diff --git a/CHANGELOG.md b/CHANGELOG.md index 0ab9c0a..7396ea9 100644 --- a/CHANGELOG.md +++ b/CHANGELOG.md @@ -6,10 +6,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0 ## [Unreleased] ### Added -- Zenodo to automatically generate a DOI for new releases +- Integration with Zenodo to automatically generate a DOI for new releases - Citation page -- PDBQT section in the "How-to" notebook -- Example PDBQT files from Vina in the data folder +- Docking section in the Quickstart notebook (Issue #11) +- PDBQT, MOL2 and SDF molecule suppliers to make it easier for users to use docking + results as input (Issue #11) +- `Molecule.from_rdkit` classmethod to easily prepare RDKit molecules for ProLIF ### Changed - The visualisation notebook now displays the protein with py3Dmol. Some examples for creating and displaying a graph from the interaction dataframe have been added @@ -17,6 +19,9 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0 - The previous repr method of `ResidueId` was easy to confuse with a string, especially when trying to access the `Fingerprint.ifp` results by string. The new repr method is now more explicit. +- Added the `Fingerprint.run_from_iterable` method, which uses the new supplier functions + to quickly generate a fingerprint. +- Sorted the output of `Fingerprint.list_available` ### Deprecated ### Removed ### Fixed diff --git a/docs/notebooks/how-to.ipynb b/docs/notebooks/how-to.ipynb index e64dc30..097dca0 100644 --- a/docs/notebooks/how-to.ipynb +++ b/docs/notebooks/how-to.ipynb @@ -6,7 +6,15 @@ "source": [ "# How-to\n", "\n", - "This notebook serves as a practical guide to common questions users might have." + "This notebook serves as a practical guide to common questions users might have.\n", + "\n", + "**Table of content**\n", + "\n", + "- [Changing the parameters for an interaction](#Changing-the-parameters-for-an-interaction)\n", + "- [Writing your own interaction](#Writing-your-own-interaction)\n", + "- [Working with docking poses instead of MD simulations](#Working-with-docking-poses-instead-of-MD-simulations)\n", + "- [Using PDBQT files](#Using-PDBQT-files)\n", + "\n" ] }, { @@ -17,6 +25,7 @@ "source": [ "import MDAnalysis as mda\n", "import prolif as plf\n", + "import pandas as pd\n", "import numpy as np" ] }, @@ -37,7 +46,7 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "## 1. Changing the parameters for an interaction" + "## Changing the parameters for an interaction" ] }, { @@ -81,7 +90,7 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "### 1.a Overwriting the original interaction" + "### Overwriting the original interaction" ] }, { @@ -136,7 +145,7 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "### 1.b Reparameterizing an interaction with another name" + "### Reparameterizing an interaction with another name" ] }, { @@ -183,7 +192,7 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "## 2. Writing your own interaction" + "## Writing your own interaction" ] }, { @@ -339,19 +348,17 @@ ] }, { - "cell_type": "markdown", - "metadata": {}, "source": [ - "## 3. Using PDBQT files\n", + "## Working with docking poses instead of MD simulations\n", "\n", - "The typical use case here is getting the IFP from AutoDock Vina's output. It requires a few additional steps and informations compared to other formats like MOL2, since the PDBQT format gets rid of most hydrogen atoms and doesn't contain bond order information.\n", + "ProLIF currently provides file readers for MOL2, SDF and PDBQT files. The API is slightly different compared to the quickstart example but the end result is the same.\n", "\n", - "The prerequisites for a successfull usage of ProLIF in this case is having external files (typically in the MOL2 format) that contain bond orders and formal charges for your ligand and protein, or at least a PDB file with explicit hydrogen atoms. \n", + "Please note that this part of the tutorial is only suitable for interactions between one protein and several ligands, or in more general terms, between one molecule with multiple residues and one molecule with a single residue. This is not suitable for protein-protein or DNA-protein interactions.\n", "\n", - "Please note that your PDBQT input must have a single model per file. Splitting a multi-model file can be done using the `vina_split` command-line tool that comes with AutoDock Vina: `vina_split --input vina_output.pdbqt`\n", - "\n", - "Let's start by loading our \"template\" file with bond orders. It can be a SMILES string, MOL2, SDF file or anything supported by RDKit." - ] + "Let's start by loading the protein. Here I'm using a PDB file but you can use any format supported by MDAnalysis as long as it contains explicit hydrogens." + ], + "cell_type": "markdown", + "metadata": {} }, { "cell_type": "code", @@ -359,25 +366,45 @@ "metadata": {}, "outputs": [], "source": [ - "from rdkit import Chem\n", - "from rdkit.Chem import AllChem\n", - "\n", - "template = Chem.MolFromSmiles(\"C[NH+]1CC(C(=O)NC2(C)OC3(O)C4CCCN4C(=O)C\"\n", - " \"(Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)CC21\")\n", - "template" + "# load protein\n", + "prot = mda.Universe(plf.datafiles.datapath / \"vina\" / \"rec.pdb\")\n", + "prot = plf.Molecule.from_mda(prot)\n", + "prot.n_residues" ] }, { + "source": [ + "### Using an SDF file" + ], "cell_type": "markdown", + "metadata": {} + }, + { + "cell_type": "code", + "execution_count": null, "metadata": {}, + "outputs": [], "source": [ - "Next, we'll define a function that loads a PDBQT file and assigns bond orders and charges using the template. The template and PDBQT file must have the exact same atoms (even hydrogens) otherwise no match will be found. Since PDBQT files partially keep the hydrogen atoms, we have the choice between:\n", + "# load ligands\n", + "path = str(plf.datafiles.datapath / \"vina\" / \"vina_output.sdf\")\n", + "lig_suppl = list(plf.sdf_supplier(path))\n", + "# generate fingerprint\n", + "fp = plf.Fingerprint()\n", + "fp.run_from_iterable(lig_suppl, prot)\n", + "df = fp.to_dataframe()\n", + "df" + ] + }, + { + "source": [ + "Please note that converting the `lig_suppl` to a list is optionnal (and maybe not suitable for large files) as it will load all the ligands in memory, but it's nicer to track the progression with the progress bar.\n", "\n", - "* Manually selecting where to add the hydrogens on the template, do the matching, then add the remaining hydrogens\n", - "* Or just remove the hydrogens from the PDBQT file, do the matching, then add all hydrogens.\n", + "If you want to calculate the Tanimoto similarity between your docked poses and a reference ligand, here's how to do it.\n", "\n", - "This last option will delete the coordinates of your hydrogens atoms and replace them by the ones generated by RDKit, but unless you're working with an exotic system this should be fine." - ] + "We first need to generate the interaction fingerprint for the reference, and concatenate it to the previous one" + ], + "cell_type": "markdown", + "metadata": {} }, { "cell_type": "code", @@ -385,32 +412,29 @@ "metadata": {}, "outputs": [], "source": [ - "mda_to_rdkit = mda._CONVERTERS[\"RDKIT\"]().convert\n", - "\n", - "def pdbqt_to_rdkit(pdbqt, template):\n", - " pdbqt = mda.Universe(pdbqt)\n", - " # set attributes needed by the converter\n", - " elements = [mda.topology.guessers.guess_atom_element(x)\n", - " for x in pdbqt.atoms.names]\n", - " pdbqt.add_TopologyAttr(\"elements\", elements)\n", - " pdbqt.add_TopologyAttr(\"chainIDs\", pdbqt.atoms.segids)\n", - " pdbqt.atoms.types = pdbqt.atoms.elements\n", - " # convert without infering bond orders and charges\n", - " mol = mda_to_rdkit(pdbqt.atoms, NoImplicit=False)\n", - " # assign BO from template then add hydrogens\n", - " mol = Chem.RemoveHs(mol, sanitize=False)\n", - " mol = AllChem.AssignBondOrdersFromTemplate(template, mol)\n", - " mol = Chem.AddHs(mol, addCoords=True, addResidueInfo=True)\n", - " return mol\n", - "\n", - "pdbqt_to_rdkit(plf.datafiles.datapath / \"vina/vina_output_ligand_1.pdbqt\", template)" + "# load the reference\n", + "ref = mda.Universe(plf.datafiles.datapath / \"vina\" / \"lig.pdb\")\n", + "ref = plf.Molecule.from_mda(ref)\n", + "# generate IFP\n", + "fp.run_from_iterable([ref], prot)\n", + "df0 = fp.to_dataframe()\n", + "df0.rename({0: \"ref\"}, inplace=True)\n", + "# drop the ligand level on both dataframes\n", + "df0.columns = df0.columns.droplevel(0)\n", + "df.columns = df.columns.droplevel(0)\n", + "# concatenate them\n", + "df = (pd.concat([df0, df])\n", + " .fillna(False)\n", + " .sort_index(axis=1, level=0,\n", + " key=lambda index: [plf.ResidueId.from_string(x) for x in index]))\n", + "df" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ - "Now our ligand is ready to be used. For the protein, there's usually no need to load the PDBQT that was used by Vina. The original file that was used to generate the PDBQT can be used directly, but **it must contain explicit hydrogen atoms**:" + "Lastly, we can convert the dataframe to a list of RDKit bitvectors to finally compute the Tanimoto similarity between our reference pose and the docking poses generated by Vina:" ] }, { @@ -419,51 +443,43 @@ "metadata": {}, "outputs": [], "source": [ - "prot = mda.Universe(plf.datafiles.datapath / \"vina/rec.pdb\")\n", - "prot = plf.Molecule.from_mda(prot)\n", - "prot.GetNumHeavyAtoms()" + "from rdkit import DataStructs\n", + "\n", + "bvs = plf.to_bitvectors(df)\n", + "for i, bv in enumerate(bvs[1:]):\n", + " tc = DataStructs.TanimotoSimilarity(bvs[0], bv)\n", + " print(f\"{i}: {tc:.3f}\")" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ - "We are now ready to compute the IFP for our docking poses (we will also do it for the reference structure):" + "Interestingly, the best scored docking pose (#0) isn't the most similar to the reference (#5)" ] }, + { + "source": [ + "### Using a MOL2 file\n", + "\n", + "The input mol2 file can contain multiple ligands in different conformations." + ], + "cell_type": "markdown", + "metadata": {} + }, { "cell_type": "code", "execution_count": null, "metadata": {}, "outputs": [], "source": [ + "# load ligands\n", + "path = plf.datafiles.datapath / \"vina\" / \"vina_output.mol2\"\n", + "lig_suppl = list(plf.mol2_supplier(path))\n", + "# generate fingerprint\n", "fp = plf.Fingerprint()\n", - "ifp = []\n", - "\n", - "# equivalent to what happens in the fp.run method\n", - "def run_fp(lig, prot, frame=0):\n", - " data = {\"Frame\": frame}\n", - " for lres in lig:\n", - " for presid in plf.get_residues_near_ligand(lres, prot):\n", - " bv = fp.bitvector(lres, prot[presid])\n", - " data[(lres.resid, presid)] = bv\n", - " return data\n", - "\n", - "# original structure for reference\n", - "lig = mda.Universe(plf.datafiles.datapath / \"vina/lig.pdb\")\n", - "lig = plf.Molecule.from_mda(lig)\n", - "data = run_fp(lig, prot, frame=0)\n", - "ifp.append(data)\n", - "\n", - "# docking poses\n", - "pdbqt_files = sorted((plf.datafiles.datapath / \"vina\").glob(\"*.pdbqt\"))\n", - "for i, pdbqt in enumerate(pdbqt_files, start=1):\n", - " lig = pdbqt_to_rdkit(pdbqt, template)\n", - " lig = plf.Molecule(lig)\n", - " data = run_fp(lig, prot, frame=i)\n", - " ifp.append(data)\n", - "\n", - "df = plf.to_dataframe(ifp, fp.interactions.keys())\n", + "fp.run_from_iterable(lig_suppl, prot)\n", + "df = fp.to_dataframe()\n", "df" ] }, @@ -471,7 +487,15 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "Lastly, we can now compute the Tanimoto similarity between our reference pose and the docking poses generated by Vina:" + "### Using PDBQT files\n", + "\n", + "The typical use case here is getting the IFP from AutoDock Vina's output. It requires a few additional steps and informations compared to other formats like MOL2, since the PDBQT format gets rid of most hydrogen atoms and doesn't contain bond order information.\n", + "\n", + "The prerequisites for a successfull usage of ProLIF in this case is having external files that contain bond orders and formal charges for your ligand (like SMILES, SDF or MOL2), or at least a file with explicit hydrogen atoms. \n", + "\n", + "Please note that your PDBQT input must have a single model per file (this is required by MDAnalysis). Splitting a multi-model file can be done using the `vina_split` command-line tool that comes with AutoDock Vina: `vina_split --input vina_output.pdbqt`\n", + "\n", + "Let's start by loading our \"template\" file with bond orders. It can be a SMILES string, MOL2, SDF file or anything supported by RDKit." ] }, { @@ -480,24 +504,26 @@ "metadata": {}, "outputs": [], "source": [ - "from rdkit import DataStructs\n", + "from rdkit import Chem\n", + "from rdkit.Chem import AllChem\n", "\n", - "bvs = plf.to_bitvectors(df)\n", - "DataStructs.BulkTanimotoSimilarity(bvs[0], bvs[1:])" - ] - }, - { - "cell_type": "markdown", - "metadata": {}, - "source": [ - "Interestingly, the best scored docking pose (#1) isn't the most similar to the reference (#6)!" + "template = Chem.MolFromSmiles(\"C[NH+]1CC(C(=O)NC2(C)OC3(O)C4CCCN4C(=O)C\"\n", + " \"(Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)CC21\")\n", + "template" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ - "## 4. Ignoring the protein backbone when computing interactions" + "Next, we'll use the PDBQT supplier which loads each file from a list of paths, and assigns bond orders and charges using the template. The template and PDBQT file must have the exact same atoms, **even hydrogens**, otherwise no match will be found. Since PDBQT files partially keep the hydrogen atoms, we have the choice between:\n", + "\n", + "* Manually selecting where to add the hydrogens on the template, do the matching, then add the remaining hydrogens (not covered here)\n", + "* Or just remove the hydrogens from the PDBQT file, do the matching, then add all hydrogens.\n", + "\n", + "This last option will delete the coordinates of your hydrogens atoms and replace them by the ones generated by RDKit, but unless you're working with an exotic system this should be fine.\n", + "\n", + "For the protein, there's usually no need to load the PDBQT that was used by Vina. The original file that was used to generate the PDBQT can be used directly, but **it must contain explicit hydrogen atoms**:" ] }, { @@ -506,7 +532,14 @@ "metadata": {}, "outputs": [], "source": [ - "# not implemented yet" + "# load ligands\n", + "pdbqt_files = sorted(plf.datafiles.datapath.glob(\"vina/*.pdbqt\"))\n", + "lig_suppl = list(plf.pdbqt_supplier(pdbqt_files, template))\n", + "# generate fingerprint\n", + "fp = plf.Fingerprint()\n", + "fp.run_from_iterable(lig_suppl, prot)\n", + "df = fp.to_dataframe()\n", + "df" ] } ], @@ -526,9 +559,9 @@ "name": "python", "nbconvert_exporter": "python", "pygments_lexer": "ipython3", - "version": "3.8.5" + "version": "3.8.5-final" } }, "nbformat": 4, "nbformat_minor": 2 -} +} \ No newline at end of file diff --git a/docs/notebooks/quickstart.ipynb b/docs/notebooks/quickstart.ipynb index 9268388..f023186 100644 --- a/docs/notebooks/quickstart.ipynb +++ b/docs/notebooks/quickstart.ipynb @@ -232,7 +232,7 @@ "cell_type": "markdown", "metadata": {}, "source": [ - "You can also compute a Tanimoto similarity between each frames:" + "You can also compute a Tanimoto similarity between each frame:" ] }, { @@ -269,4 +269,4 @@ }, "nbformat": 4, "nbformat_minor": 2 -} +} \ No newline at end of file diff --git a/prolif/__init__.py b/prolif/__init__.py index ee651ad..d23658a 100644 --- a/prolif/__init__.py +++ b/prolif/__init__.py @@ -1,7 +1,12 @@ -from .molecule import Molecule +from .molecule import (Molecule, + pdbqt_supplier, + mol2_supplier, + sdf_supplier) from .residue import ResidueId from .fingerprint import Fingerprint -from .utils import get_residues_near_ligand, to_dataframe, to_bitvectors +from .utils import (get_residues_near_ligand, + to_dataframe, + to_bitvectors) from . import datafiles from ._version import get_versions __version__ = get_versions()['version'] diff --git a/prolif/data/vina/vina_output.mol2 b/prolif/data/vina/vina_output.mol2 new file mode 100644 index 0000000..5fe2274 --- /dev/null +++ b/prolif/data/vina/vina_output.mol2 @@ -0,0 +1,1566 @@ +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 1.4240 1.3400 12.7270 C.3 1 noname 0.2017 +2 C2 2.4870 0.8460 13.7760 C.2 1 noname 0.0859 +3 C3 4.0730 1.9290 15.2560 C.3 1 noname 0.1001 +4 O1 2.0390 2.5820 12.2920 O.3 1 noname -0.3049 +5 C4 3.9120 3.3800 15.9040 C.2 1 noname 0.0539 +6 C5 3.4980 5.8160 15.5500 C.3 1 noname 0.0065 +7 C6 2.6560 6.4710 14.4840 C.3 1 noname -0.0381 +8 C7 2.6580 5.5380 13.2830 C.3 1 noname -0.0291 +9 C8 2.7950 4.1300 14.0210 C.3 1 noname 0.0870 +10 C9 3.1900 2.9120 13.1250 C.3 1 noname 0.2535 +11 C10 0.2490 1.4570 13.7150 C.3 1 noname -0.0125 +12 O2 2.4730 -0.2350 14.4210 O.2 1 noname -0.2735 +13 N1 3.4540 1.8360 13.9640 N.3 1 noname -0.0076 +14 O3 4.1160 3.4310 17.1140 O.2 1 noname -0.2883 +15 N2 3.6390 4.3990 15.1010 N.3 1 noname -0.0572 +16 N3 1.2210 0.6180 11.5910 N.3 1 noname -0.0502 +17 C11 0.6920 1.1580 10.4110 C.2 1 noname 0.0544 +18 O4 0.3000 2.3070 10.3880 O.2 1 noname -0.2899 +19 C12 0.7180 0.2040 9.2400 C.3 1 noname 0.0996 +20 C13 1.2190 1.0110 8.0210 C.3 1 noname 0.0041 +21 N4 1.2970 0.0640 6.8800 N.4 1 noname 0.0094 +22 C14 1.3330 0.9250 5.5640 C.3 1 noname -0.0218 +23 C15 2.2380 -1.0390 6.9860 C.3 1 noname 0.0303 +24 C16 2.0880 -2.1970 5.9570 C.3 1 noname 0.0498 +25 C17 2.3040 -1.4620 8.5110 C.2 1 noname -0.0158 +26 C18 3.1050 -3.3550 6.1960 C.2 1 noname -0.0271 +27 C19 3.7040 -4.3130 5.5140 C.2 1 noname -0.1133 +28 C20 3.5500 -3.3880 7.5780 C.2 1 noname -0.0193 +29 N5 4.5340 -5.0360 6.4660 N.3 1 noname -0.0790 +30 C21 4.3780 -4.5210 7.7400 C.2 1 noname -0.0845 +31 C22 4.8510 -4.8830 8.9500 C.2 1 noname -0.0420 +32 C23 4.5410 -4.0450 10.0910 C.2 1 noname -0.0462 +33 C24 3.7890 -2.9380 9.9940 C.2 1 noname -0.0383 +34 C25 3.2150 -2.6450 8.7010 C.2 1 noname -0.0179 +35 C26 1.6230 -0.9550 9.5220 C.2 1 noname -0.0320 +36 O5 4.3150 2.9760 12.3150 O.3 1 noname -0.3514 +37 C27 5.5740 1.6220 15.1920 C.3 1 noname -0.0030 +38 C28 5.9870 0.3810 14.5030 C.2 1 noname -0.0541 +39 C29 6.4950 0.4310 13.2290 C.2 1 noname -0.0567 +40 C30 6.5700 -0.7570 12.4530 C.2 1 noname -0.0604 +41 C31 6.2220 -2.0410 12.9850 C.2 1 noname -0.0616 +42 C32 5.7500 -2.0670 14.2970 C.2 1 noname -0.0604 +43 C33 5.5910 -0.8980 15.0340 C.2 1 noname -0.0567 +44 H1 3.5551 1.1833 15.8771 H 1 noname 0.0574 +45 H2 4.4828 6.3011 15.6196 H 1 noname 0.0435 +46 H3 3.0421 5.8939 16.5480 H 1 noname 0.0435 +47 H4 1.6284 6.6150 14.8492 H 1 noname 0.0280 +48 H5 3.0594 7.4586 14.2156 H 1 noname 0.0280 +49 H6 1.7214 5.6086 12.7104 H 1 noname 0.0286 +50 H7 3.4394 5.7466 12.5374 H 1 noname 0.0286 +51 H8 1.8162 3.7547 14.3544 H 1 noname 0.0544 +52 H9 0.6314 1.4189 14.7457 H 1 noname 0.0279 +53 H10 -0.2730 2.4116 13.5526 H 1 noname 0.0279 +54 H11 -0.4509 0.6241 13.5526 H 1 noname 0.0279 +55 H12 1.4702 -0.3814 11.5992 H 1 noname 0.1344 +56 H13 -0.2819 -0.2125 9.0483 H 1 noname 0.0509 +57 H14 0.5151 1.8242 7.7903 H 1 noname 0.0951 +58 H15 2.2005 1.4640 8.2248 H 1 noname 0.0951 +59 H16 0.4494 -0.5211 6.8735 H 1 noname 0.2583 +60 H17 1.3776 1.9926 5.8254 H 1 noname 0.0902 +61 H18 2.2206 0.6547 4.9732 H 1 noname 0.0902 +62 H19 0.4259 0.7298 4.9732 H 1 noname 0.0902 +63 H20 3.2277 -0.6832 6.6636 H 1 noname 0.1037 +64 H21 1.0687 -2.6037 6.0320 H 1 noname 0.0390 +65 H22 2.2895 -1.7807 4.9590 H 1 noname 0.0390 +66 H23 3.5972 -4.5232 4.4396 H 1 noname 0.0792 +67 H24 5.1527 -5.8232 6.2242 H 1 noname 0.1522 +68 H25 5.4578 -5.7929 9.0681 H 1 noname 0.0642 +69 H26 4.9384 -4.3280 11.0769 H 1 noname 0.0623 +70 H27 3.6172 -2.2826 10.8606 H 1 noname 0.0629 +71 H28 1.7172 -1.3697 10.5365 H 1 noname 0.0592 +72 H29 5.1264 3.0222 12.8803 H 1 noname 0.2151 +73 H30 6.0608 2.4630 14.6765 H 1 noname 0.0337 +74 H31 5.8754 1.4751 16.2396 H 1 noname 0.0337 +75 H32 6.8427 1.3869 12.8103 H 1 noname 0.0625 +76 H33 6.9068 -0.6885 11.4081 H 1 noname 0.0622 +77 H34 6.3221 -2.9599 12.3887 H 1 noname 0.0622 +78 H35 5.4980 -3.0329 14.7591 H 1 noname 0.0622 +79 H36 5.1542 -0.9514 16.0422 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 1.1200 1.1530 12.1940 C.3 1 noname 0.2017 +2 C2 1.8960 1.0940 13.5610 C.2 1 noname 0.0859 +3 C3 2.9250 2.7320 15.0240 C.3 1 noname 0.1001 +4 O1 1.7240 2.3310 11.5960 O.3 1 noname -0.3049 +5 C4 2.4720 4.2550 15.1930 C.2 1 noname 0.0539 +6 C5 1.9680 6.4400 14.0980 C.3 1 noname 0.0065 +7 C6 1.3950 6.6810 12.7240 C.3 1 noname -0.0381 +8 C7 1.8010 5.4980 11.8610 C.3 1 noname -0.0291 +9 C8 1.8500 4.3480 12.9660 C.3 1 noname 0.0870 +10 C9 2.5740 3.0240 12.5580 C.3 1 noname 0.2535 +11 C10 -0.2840 1.3250 12.8010 C.3 1 noname -0.0125 +12 O2 1.7980 0.2120 14.4540 O.2 1 noname -0.2735 +13 N1 2.6890 2.2350 13.6980 N.3 1 noname -0.0076 +14 O3 2.3360 4.6270 16.3560 O.2 1 noname -0.2883 +15 N2 2.3440 4.9950 14.1010 N.3 1 noname -0.0572 +16 N3 1.2950 0.1540 11.2840 N.3 1 noname -0.0502 +17 C11 1.0100 0.2900 9.9190 C.2 1 noname 0.0544 +18 O4 0.4970 1.3070 9.5000 O.2 1 noname -0.2899 +19 C12 1.4410 -0.8960 9.0880 C.3 1 noname 0.0996 +20 C13 2.8070 -1.3550 9.6470 C.3 1 noname 0.0041 +21 N4 3.2100 -2.5530 8.8680 N.4 1 noname 0.0094 +22 C14 4.7580 -2.7440 9.0770 C.3 1 noname -0.0218 +23 C15 2.3700 -3.7350 8.9710 C.3 1 noname 0.0303 +24 C16 2.6000 -4.8600 7.9200 C.3 1 noname 0.0498 +25 C17 0.8750 -3.2410 9.1500 C.2 1 noname -0.0158 +26 C18 1.6080 -6.0520 8.0820 C.2 1 noname -0.0271 +27 C19 1.5470 -7.3420 7.8120 C.2 1 noname -0.1133 +28 C20 0.3870 -5.6340 8.7470 C.2 1 noname -0.0193 +29 N5 0.2380 -7.7940 8.2610 N.3 1 noname -0.0790 +30 C21 -0.4990 -6.7340 8.7590 C.2 1 noname -0.0845 +31 C22 -1.7650 -6.6190 9.2100 C.2 1 noname -0.0420 +32 C23 -2.1920 -5.3410 9.7450 C.2 1 noname -0.0462 +33 C24 -1.3850 -4.2690 9.7930 C.2 1 noname -0.0383 +34 C25 -0.0740 -4.4070 9.2030 C.2 1 noname -0.0179 +35 C26 0.4310 -1.9980 9.1730 C.2 1 noname -0.0320 +36 O5 3.8670 3.0610 12.0560 O.3 1 noname -0.3514 +37 C27 4.4070 2.6500 15.4080 C.3 1 noname -0.0030 +38 C28 5.0700 1.3340 15.2930 C.2 1 noname -0.0541 +39 C29 5.8450 1.0410 14.2000 C.2 1 noname -0.0567 +40 C30 6.1950 -0.3080 13.9250 C.2 1 noname -0.0604 +41 C31 5.8470 -1.3830 14.8060 C.2 1 noname -0.0616 +42 C32 5.0960 -1.0490 15.9320 C.2 1 noname -0.0604 +43 C33 4.6750 0.2560 16.1630 C.2 1 noname -0.0567 +44 H1 2.3226 2.0893 15.6829 H 1 noname 0.0574 +45 H2 2.8526 7.0718 14.2662 H 1 noname 0.0435 +46 H3 1.2536 6.6869 14.8972 H 1 noname 0.0435 +47 H4 0.2986 6.7504 12.7786 H 1 noname 0.0280 +48 H5 1.7717 7.6239 12.3008 H 1 noname 0.0280 +49 H6 1.0526 5.2847 11.0836 H 1 noname 0.0286 +50 H7 2.7351 5.6367 11.2969 H 1 noname 0.0286 +51 H8 0.8524 3.9204 13.1448 H 1 noname 0.0544 +52 H9 -0.2125 1.3162 13.8986 H 1 noname 0.0279 +53 H10 -0.7122 2.2823 12.4691 H 1 noname 0.0279 +54 H11 -0.9306 0.4994 12.4691 H 1 noname 0.0279 +55 H12 1.6566 -0.7508 11.6180 H 1 noname 0.1344 +56 H13 1.5245 -0.6239 8.0255 H 1 noname 0.0509 +57 H14 3.5533 -0.5561 9.5258 H 1 noname 0.0951 +58 H15 2.7358 -1.5879 10.7197 H 1 noname 0.0951 +59 H16 3.0258 -2.3782 7.8698 H 1 noname 0.2583 +60 H17 4.9820 -2.7716 10.1536 H 1 noname 0.0902 +61 H18 5.0771 -3.6883 8.6117 H 1 noname 0.0902 +62 H19 5.2970 -1.9056 8.6117 H 1 noname 0.0902 +63 H20 2.6768 -4.3014 9.8627 H 1 noname 0.1037 +64 H21 2.4739 -4.4323 6.9144 H 1 noname 0.0390 +65 H22 3.6162 -5.2524 8.0728 H 1 noname 0.0390 +66 H23 2.3299 -7.9545 7.3410 H 1 noname 0.0792 +67 H24 -0.0937 -8.7680 8.2144 H 1 noname 0.1522 +68 H25 -2.4564 -7.4738 9.1728 H 1 noname 0.0642 +69 H26 -3.2191 -5.2457 10.1272 H 1 noname 0.0623 +70 H27 -1.7080 -3.3274 10.2610 H 1 noname 0.0629 +71 H28 -0.6442 -1.7794 9.2519 H 1 noname 0.0592 +72 H29 4.5121 3.0795 12.8068 H 1 noname 0.2151 +73 H30 4.9541 3.3522 14.7618 H 1 noname 0.0337 +74 H31 4.4313 2.8830 16.4828 H 1 noname 0.0337 +75 H32 6.1943 1.8477 13.5387 H 1 noname 0.0625 +76 H33 6.7523 -0.5351 13.0042 H 1 noname 0.0622 +77 H34 6.1566 -2.4190 14.6042 H 1 noname 0.0622 +78 H35 4.8305 -1.8354 16.6539 H 1 noname 0.0622 +79 H36 4.0279 0.4692 17.0266 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 1.1630 1.1080 12.2000 C.3 1 noname 0.2017 +2 C2 1.8410 0.9760 13.6120 C.2 1 noname 0.0859 +3 C3 2.8680 2.5190 15.1770 C.3 1 noname 0.1001 +4 O1 1.8760 2.2570 11.6690 O.3 1 noname -0.3049 +5 C4 2.4990 4.0640 15.3490 C.2 1 noname 0.0539 +6 C5 2.2040 6.2960 14.2730 C.3 1 noname 0.0065 +7 C6 1.7390 6.5980 12.8710 C.3 1 noname -0.0381 +8 C7 2.1290 5.4080 12.0100 C.3 1 noname -0.0291 +9 C8 2.0340 4.2370 13.0890 C.3 1 noname 0.0870 +10 C9 2.7010 2.8780 12.7000 C.3 1 noname 0.2535 +11 C10 -0.2660 1.3570 12.7170 C.3 1 noname -0.0125 +12 O2 1.6290 0.0860 14.4770 O.2 1 noname -0.2735 +13 N1 2.6910 2.0630 13.8270 N.3 1 noname -0.0076 +14 O3 2.3080 4.4220 16.5090 O.2 1 noname -0.2883 +15 N2 2.4890 4.8310 14.2680 N.3 1 noname -0.0572 +16 N3 1.3370 0.1180 11.2810 N.3 1 noname -0.0502 +17 C11 1.1390 0.2920 9.9040 C.2 1 noname 0.0544 +18 O4 0.7050 1.3430 9.4780 O.2 1 noname -0.2899 +19 C12 1.5530 -0.9000 9.0750 C.3 1 noname 0.0996 +20 C13 2.9080 -1.3830 9.6410 C.3 1 noname 0.0041 +21 N4 3.2940 -2.5880 8.8640 N.4 1 noname 0.0094 +22 C14 4.8370 -2.8060 9.0810 C.3 1 noname -0.0218 +23 C15 2.4330 -3.7550 8.9620 C.3 1 noname 0.0303 +24 C16 2.6490 -4.8830 7.9120 C.3 1 noname 0.0498 +25 C17 0.9460 -3.2350 9.1330 C.2 1 noname -0.0158 +26 C18 1.6360 -6.0580 8.0680 C.2 1 noname -0.0271 +27 C19 1.5540 -7.3470 7.7960 C.2 1 noname -0.1133 +28 C20 0.4190 -5.6200 8.7260 C.2 1 noname -0.0193 +29 N5 0.2350 -7.7760 8.2390 N.3 1 noname -0.0790 +30 C21 -0.4860 -6.7040 8.7330 C.2 1 noname -0.0845 +31 C22 -1.7530 -6.5660 9.1770 C.2 1 noname -0.0420 +32 C23 -2.1590 -5.2820 9.7110 C.2 1 noname -0.0462 +33 C24 -1.3350 -4.2240 9.7640 C.2 1 noname -0.0383 +34 C25 -0.0230 -4.3850 9.1810 C.2 1 noname -0.0179 +35 C26 0.5240 -1.9840 9.1550 C.2 1 noname -0.0320 +36 O5 4.0240 2.8430 12.2850 O.3 1 noname -0.3514 +37 C27 4.3140 2.3380 15.6550 C.3 1 noname -0.0030 +38 C28 4.5520 1.3830 16.7580 C.2 1 noname -0.0541 +39 C29 4.5630 0.0330 16.5160 C.2 1 noname -0.0567 +40 C30 4.4520 -0.8780 17.6010 C.2 1 noname -0.0604 +41 C31 4.4240 -0.4430 18.9660 C.2 1 noname -0.0616 +42 C32 4.4590 0.9340 19.1830 C.2 1 noname -0.0604 +43 C33 4.4790 1.8360 18.1230 C.2 1 noname -0.0567 +44 H1 2.1856 1.9029 15.7809 H 1 noname 0.0574 +45 H2 3.1129 6.8676 14.5122 H 1 noname 0.0435 +46 H3 1.4549 6.5726 15.0295 H 1 noname 0.0435 +47 H4 0.6476 6.7343 12.8557 H 1 noname 0.0280 +48 H5 2.1990 7.5236 12.4946 H 1 noname 0.0280 +49 H6 1.4227 5.2562 11.1805 H 1 noname 0.0286 +50 H7 3.1055 5.4988 11.5118 H 1 noname 0.0286 +51 H8 1.0026 3.8687 13.1918 H 1 noname 0.0544 +52 H9 -0.2632 1.3565 13.8170 H 1 noname 0.0279 +53 H10 -0.6236 2.3310 12.3517 H 1 noname 0.0279 +54 H11 -0.9319 0.5614 12.3517 H 1 noname 0.0279 +55 H12 1.6305 -0.8106 11.6164 H 1 noname 0.1344 +56 H13 1.6464 -0.6290 8.0130 H 1 noname 0.0509 +57 H14 3.6688 -0.5973 9.5237 H 1 noname 0.0951 +58 H15 2.8272 -1.6147 10.7133 H 1 noname 0.0951 +59 H16 3.1179 -2.4099 7.8649 H 1 noname 0.2583 +60 H17 5.0550 -2.8368 10.1588 H 1 noname 0.0902 +61 H18 5.1418 -3.7561 8.6180 H 1 noname 0.0902 +62 H19 5.3931 -1.9775 8.6180 H 1 noname 0.0902 +63 H20 2.7249 -4.3269 9.8551 H 1 noname 0.1037 +64 H21 2.5355 -4.4527 6.9060 H 1 noname 0.0390 +65 H22 3.6575 -5.2929 8.0700 H 1 noname 0.0390 +66 H23 2.3281 -7.9727 7.3278 H 1 noname 0.0792 +67 H24 -0.1131 -8.7442 8.1911 H 1 noname 0.1522 +68 H25 -2.4599 -7.4077 9.1345 H 1 noname 0.0642 +69 H26 -3.1859 -5.1695 10.0889 H 1 noname 0.0623 +70 H27 -1.6446 -3.2770 10.2303 H 1 noname 0.0629 +71 H28 -0.5475 -1.7465 9.2296 H 1 noname 0.0592 +72 H29 4.6179 2.8273 13.0769 H 1 noname 0.2151 +73 H30 4.9067 1.9998 14.7922 H 1 noname 0.0337 +74 H31 4.5991 3.3180 16.0654 H 1 noname 0.0337 +75 H32 4.6573 -0.3429 15.4865 H 1 noname 0.0625 +76 H33 4.3852 -1.9546 17.3855 H 1 noname 0.0622 +77 H34 4.3773 -1.1587 19.8000 H 1 noname 0.0622 +78 H35 4.4711 1.3158 20.2145 H 1 noname 0.0622 +79 H36 4.4383 2.9152 18.3320 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 2.9670 0.4730 11.2610 C.3 1 noname 0.2017 +2 C2 2.7690 -0.9680 10.6640 C.2 1 noname 0.0859 +3 C3 1.8690 -1.8640 8.5980 C.3 1 noname 0.1001 +4 O1 1.8680 1.1780 10.6240 O.3 1 noname -0.3049 +5 C4 1.8700 -1.1300 7.1790 C.2 1 noname 0.0539 +6 C5 1.2780 0.8990 5.8510 C.3 1 noname 0.0065 +7 C6 1.2380 2.3330 6.3140 C.3 1 noname -0.0381 +8 C7 0.9350 2.3090 7.8030 C.3 1 noname -0.0291 +9 C8 1.6220 0.9270 8.2080 C.3 1 noname 0.0870 +10 C9 1.2370 0.3440 9.6060 C.3 1 noname 0.2535 +11 C10 4.3730 0.7100 10.6790 C.3 1 noname -0.0125 +12 O2 3.4330 -2.0020 10.9390 O.2 1 noname -0.2735 +13 N1 1.7680 -0.9390 9.6910 N.3 1 noname -0.0076 +14 O3 2.2820 -1.8140 6.2450 O.2 1 noname -0.2883 +15 N2 1.3820 0.1000 7.1090 N.3 1 noname -0.0572 +16 N3 2.7980 0.6710 12.5980 N.3 1 noname -0.0502 +17 C11 3.6850 0.1930 13.5720 C.2 1 noname 0.0544 +18 O4 4.6190 -0.5130 13.2530 O.2 1 noname -0.2899 +19 C12 3.3740 0.6810 14.9680 C.3 1 noname 0.0996 +20 C13 4.5310 0.1990 15.8720 C.3 1 noname 0.0041 +21 N4 4.2580 0.7210 17.2350 N.4 1 noname 0.0094 +22 C14 5.1240 -0.1260 18.2390 C.3 1 noname -0.0218 +23 C15 4.2460 2.1640 17.4120 C.3 1 noname 0.0303 +24 C16 3.6450 2.7080 18.7410 C.3 1 noname 0.0498 +25 C17 3.6820 2.8020 16.0770 C.2 1 noname -0.0158 +26 C18 3.6250 4.2670 18.8030 C.2 1 noname -0.0271 +27 C19 3.6280 5.2280 19.7060 C.2 1 noname -0.1133 +28 C20 3.6210 4.8460 17.4720 C.2 1 noname -0.0193 +29 N5 3.5790 6.4830 18.9690 N.3 1 noname -0.0790 +30 C21 3.4930 6.2460 17.6080 C.2 1 noname -0.0845 +31 C22 3.3430 7.0510 16.5370 C.2 1 noname -0.0420 +32 C23 3.3750 6.4540 15.2160 C.2 1 noname -0.0462 +33 C24 3.5290 5.1350 15.0210 C.2 1 noname -0.0383 +34 C25 3.5780 4.2980 16.1970 C.2 1 noname -0.0179 +35 C26 3.2600 2.1730 14.9950 C.2 1 noname -0.0320 +36 O5 -0.0960 0.1670 9.9460 O.3 1 noname -0.3514 +37 C27 0.7110 -2.8680 8.5930 C.3 1 noname -0.0030 +38 C28 1.0450 -4.2960 8.7820 C.2 1 noname -0.0541 +39 C29 2.3360 -4.7320 8.6250 C.2 1 noname -0.0567 +40 C30 2.5970 -6.1200 8.4710 C.2 1 noname -0.0604 +41 C31 1.5640 -7.1080 8.5690 C.2 1 noname -0.0616 +42 C32 0.2670 -6.6380 8.7730 C.2 1 noname -0.0604 +43 C33 -0.0090 -5.2760 8.8370 C.2 1 noname -0.0567 +44 H1 2.8262 -2.3845 8.7488 H 1 noname 0.0574 +45 H2 0.3597 0.6422 5.3026 H 1 noname 0.0435 +46 H3 2.1146 0.7056 5.1635 H 1 noname 0.0435 +47 H4 2.2098 2.8158 6.1337 H 1 noname 0.0280 +48 H5 0.4725 2.9020 5.7660 H 1 noname 0.0280 +49 H6 1.3940 3.1609 8.3260 H 1 noname 0.0286 +50 H7 -0.1322 2.3863 8.0583 H 1 noname 0.0286 +51 H8 2.6989 1.0529 8.3938 H 1 noname 0.0544 +52 H9 5.0942 0.8316 11.5006 H 1 noname 0.0279 +53 H10 4.6638 -0.1518 10.0603 H 1 noname 0.0279 +54 H11 4.3652 1.6195 10.0603 H 1 noname 0.0279 +55 H12 1.9723 1.2016 12.9105 H 1 noname 0.1344 +56 H13 2.4105 0.2838 15.3199 H 1 noname 0.0509 +57 H14 4.5663 -0.9003 15.8878 H 1 noname 0.0951 +58 H15 5.5003 0.5606 15.4982 H 1 noname 0.0951 +59 H16 3.2610 0.5801 17.4520 H 1 noname 0.2583 +60 H17 4.8527 0.1394 19.2715 H 1 noname 0.0902 +61 H18 4.9344 -1.1969 18.0737 H 1 noname 0.0902 +62 H19 6.1904 0.0873 18.0737 H 1 noname 0.0902 +63 H20 5.2808 2.5026 17.5687 H 1 noname 0.1037 +64 H21 2.6130 2.3393 18.8367 H 1 noname 0.0390 +65 H22 4.2837 2.3524 19.5629 H 1 noname 0.0390 +66 H23 3.6610 5.1059 20.7987 H 1 noname 0.0792 +67 H24 3.6048 7.4178 19.4008 H 1 noname 0.1522 +68 H25 3.1998 8.1344 16.6623 H 1 noname 0.0642 +69 H26 3.2688 7.1085 14.3383 H 1 noname 0.0623 +70 H27 3.6142 4.7102 14.0099 H 1 noname 0.0629 +71 H28 2.8391 2.7268 14.1429 H 1 noname 0.0592 +72 H29 -0.1863 0.1550 10.9318 H 1 noname 0.2151 +73 H30 0.0224 -2.5809 9.4013 H 1 noname 0.0337 +74 H31 0.2939 -2.8098 7.5768 H 1 noname 0.0337 +75 H32 3.1658 -4.0099 8.6184 H 1 noname 0.0625 +76 H33 3.6276 -6.4474 8.2696 H 1 noname 0.0622 +77 H34 1.7829 -8.1829 8.4874 H 1 noname 0.0622 +78 H35 -0.5555 -7.3597 8.8857 H 1 noname 0.0622 +79 H36 -1.0525 -4.9410 8.9314 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 4.3630 3.0650 16.3440 C.3 1 noname 0.2017 +2 C2 5.3850 3.8250 17.2660 C.2 1 noname 0.0859 +3 C3 5.4210 5.9770 18.3830 C.3 1 noname 0.1001 +4 O1 3.6990 4.1860 15.7030 O.3 1 noname -0.3049 +5 C4 4.1440 6.7850 18.9040 C.2 1 noname 0.0539 +6 C5 1.9120 7.7710 18.3790 C.3 1 noname 0.0065 +7 C6 0.8860 7.2760 17.3920 C.3 1 noname -0.0381 +8 C7 1.6430 6.5360 16.3000 C.3 1 noname -0.0291 +9 C8 2.8780 5.9790 17.1430 C.3 1 noname 0.0870 +10 C9 4.0960 5.4470 16.3210 C.3 1 noname 0.2535 +11 C10 3.5970 2.3610 17.4790 C.3 1 noname -0.0125 +12 O2 6.2650 3.3140 18.0090 O.2 1 noname -0.2735 +13 N1 5.1330 5.1970 17.2130 N.3 1 noname -0.0076 +14 O3 4.2280 7.1920 20.0600 O.2 1 noname -0.2883 +15 N2 3.1500 7.0010 18.0540 N.3 1 noname -0.0572 +16 N3 4.8310 2.2910 15.3250 N.3 1 noname -0.0502 +17 C11 5.1380 0.9300 15.4620 C.2 1 noname 0.0544 +18 O4 5.0810 0.3980 16.5510 O.2 1 noname -0.2899 +19 C12 5.4800 0.2500 14.1570 C.3 1 noname 0.0996 +20 C13 5.7630 -1.2320 14.4910 C.3 1 noname 0.0041 +21 N4 6.0470 -1.9160 13.2040 N.4 1 noname 0.0094 +22 C14 6.7880 -3.2620 13.5470 C.3 1 noname -0.0218 +23 C15 4.9750 -1.9730 12.2230 C.3 1 noname 0.0303 +24 C16 5.3650 -2.3890 10.7740 C.3 1 noname 0.0498 +25 C17 4.1310 -0.6400 12.3640 C.2 1 noname -0.0158 +26 C18 4.1560 -2.3580 9.7900 C.2 1 noname -0.0271 +27 C19 3.7740 -2.9270 8.6620 C.2 1 noname -0.1133 +28 C20 3.1240 -1.4480 10.2520 C.2 1 noname -0.0193 +29 N5 2.4780 -2.3530 8.3320 N.3 1 noname -0.0790 +30 C21 2.1190 -1.3920 9.2610 C.2 1 noname -0.0845 +31 C22 1.0800 -0.5370 9.3540 C.2 1 noname -0.0420 +32 C23 0.9770 0.2960 10.5360 C.2 1 noname -0.0462 +33 C24 1.8810 0.2630 11.5270 C.2 1 noname -0.0383 +34 C25 3.0320 -0.5880 11.3370 C.2 1 noname -0.0179 +35 C26 4.3470 0.3720 13.1850 C.2 1 noname -0.0320 +36 O5 4.6860 6.2450 15.3510 O.3 1 noname -0.3514 +37 C27 6.5350 6.9990 18.1280 C.3 1 noname -0.0030 +38 C28 7.7390 6.9230 18.9820 C.2 1 noname -0.0541 +39 C29 8.8380 6.2140 18.5700 C.2 1 noname -0.0567 +40 C30 9.8420 5.8600 19.5110 C.2 1 noname -0.0604 +41 C31 9.8020 6.3000 20.8740 C.2 1 noname -0.0616 +42 C32 8.6940 7.0570 21.2530 C.2 1 noname -0.0604 +43 C33 7.6640 7.3340 20.3610 C.2 1 noname -0.0567 +44 H1 5.7376 5.2478 19.1433 H 1 noname 0.0574 +45 H2 2.0821 8.8505 18.2538 H 1 noname 0.0435 +46 H3 1.5921 7.6257 19.4214 H 1 noname 0.0435 +47 H4 0.1797 6.5955 17.8901 H 1 noname 0.0280 +48 H5 0.3083 8.1127 16.9723 H 1 noname 0.0280 +49 H6 1.0432 5.7211 15.8686 H 1 noname 0.0286 +50 H7 1.9171 7.1506 15.4299 H 1 noname 0.0286 +51 H8 2.6237 5.0382 17.6531 H 1 noname 0.0544 +52 H9 3.9775 2.7107 18.4501 H 1 noname 0.0279 +53 H10 2.5254 2.5960 17.3989 H 1 noname 0.0279 +54 H11 3.7409 1.2734 17.3989 H 1 noname 0.0279 +55 H12 4.9667 2.7300 14.4032 H 1 noname 0.1344 +56 H13 6.3562 0.7184 13.6848 H 1 noname 0.0509 +57 H14 6.6320 -1.3098 15.1609 H 1 noname 0.0951 +58 H15 4.9040 -1.6923 15.0011 H 1 noname 0.0951 +59 H16 6.6739 -1.3222 12.6424 H 1 noname 0.2583 +60 H17 6.8516 -3.3775 14.6391 H 1 noname 0.0902 +61 H18 6.2283 -4.1076 13.1208 H 1 noname 0.0902 +62 H19 7.8019 -3.2413 13.1208 H 1 noname 0.0902 +63 H20 4.3351 -2.8363 12.4579 H 1 noname 0.1037 +64 H21 6.1361 -1.6966 10.4052 H 1 noname 0.0390 +65 H22 5.7323 -3.4251 10.8146 H 1 noname 0.0390 +66 H23 4.3256 -3.6845 8.0859 H 1 noname 0.0792 +67 H24 1.9067 -2.6245 7.5191 H 1 noname 0.1522 +68 H25 0.3292 -0.4733 8.5526 H 1 noname 0.0642 +69 H26 0.1227 0.9833 10.6241 H 1 noname 0.0623 +70 H27 1.7511 0.8577 12.4432 H 1 noname 0.0629 +71 H28 3.7167 1.2730 13.1558 H 1 noname 0.0592 +72 H29 5.2142 6.9594 15.7878 H 1 noname 0.2151 +73 H30 6.8624 6.8762 17.0851 H 1 noname 0.0337 +74 H31 6.0825 7.9726 18.3674 H 1 noname 0.0337 +75 H32 8.9419 5.9204 17.5150 H 1 noname 0.0625 +76 H33 10.6787 5.2264 19.1818 H 1 noname 0.0622 +77 H34 10.6043 6.0533 21.5850 H 1 noname 0.0622 +78 H35 8.6334 7.4438 22.2810 H 1 noname 0.0622 +79 H36 6.7752 7.8771 20.7147 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 0.8590 1.6010 12.1830 C.3 1 noname 0.2017 +2 C2 1.6390 1.1340 13.4670 C.2 1 noname 0.0859 +3 C3 3.0260 2.2280 15.1280 C.3 1 noname 0.1001 +4 O1 1.6830 2.7220 11.7660 O.3 1 noname -0.3049 +5 C4 2.9100 3.7520 15.5900 C.2 1 noname 0.0539 +6 C5 2.8510 6.1590 14.9320 C.3 1 noname 0.0065 +7 C6 2.3080 6.7620 13.6620 C.3 1 noname -0.0381 +8 C7 2.4340 5.7020 12.5790 C.3 1 noname -0.0291 +9 C8 2.2660 4.3820 13.4590 C.3 1 noname 0.0870 +10 C9 2.6840 3.0370 12.7790 C.3 1 noname 0.2535 +11 C10 -0.4620 1.9390 12.8980 C.3 1 noname -0.0125 +12 O2 1.3790 0.1400 14.1950 O.2 1 noname -0.2735 +13 N1 2.6580 2.0440 13.7530 N.3 1 noname -0.0076 +14 O3 2.8840 3.9220 16.8070 O.2 1 noname -0.2883 +15 N2 2.9130 4.6930 14.6560 N.3 1 noname -0.0572 +16 N3 0.7960 0.7750 11.1020 N.3 1 noname -0.0502 +17 C11 0.4900 1.2130 9.8070 C.2 1 noname 0.0544 +18 O4 0.1720 2.3680 9.6120 O.2 1 noname -0.2899 +19 C12 0.6450 0.1430 8.7520 C.3 1 noname 0.0996 +20 C13 1.2250 0.8380 7.4990 C.3 1 noname 0.0041 +21 N4 1.4290 -0.2190 6.4760 N.4 1 noname 0.0094 +22 C14 1.5530 0.5010 5.0820 C.3 1 noname -0.0218 +23 C15 2.3900 -1.2680 6.7760 C.3 1 noname 0.0303 +24 C16 2.3630 -2.5320 5.8690 C.3 1 noname 0.0498 +25 C17 2.3370 -1.5270 8.3380 C.2 1 noname -0.0158 +26 C18 3.3900 -3.6180 6.3130 C.2 1 noname -0.0271 +27 C19 4.0720 -4.6180 5.7900 C.2 1 noname -0.1133 +28 C20 3.7140 -3.4900 7.7220 C.2 1 noname -0.0193 +29 N5 4.8390 -5.2060 6.8780 N.3 1 noname -0.0790 +30 C21 4.5580 -4.5670 8.0730 C.2 1 noname -0.0845 +31 C22 4.9360 -4.7830 9.3500 C.2 1 noname -0.0420 +32 C23 4.5040 -3.8430 10.3650 C.2 1 noname -0.0462 +33 C24 3.7310 -2.7820 10.0880 C.2 1 noname -0.0383 +34 C25 3.2620 -2.6480 8.7290 C.2 1 noname -0.0179 +35 C26 1.5560 -0.9440 9.2290 C.2 1 noname -0.0320 +36 O5 3.9420 2.9030 12.2110 O.3 1 noname -0.3514 +37 C27 4.4670 1.7770 15.3980 C.3 1 noname -0.0030 +38 C28 4.7000 0.8970 16.5620 C.2 1 noname -0.0541 +39 C29 4.3740 -0.4340 16.5020 C.2 1 noname -0.0567 +40 C30 4.2780 -1.1910 17.7010 C.2 1 noname -0.0604 +41 C31 4.6040 -0.6390 18.9820 C.2 1 noname -0.0616 +42 C32 4.9730 0.7050 19.0070 C.2 1 noname -0.0604 +43 C33 4.9850 1.4760 17.8500 C.2 1 noname -0.0567 +44 H1 2.3177 1.6104 15.6997 H 1 noname 0.0574 +45 H2 3.8531 6.5554 15.1526 H 1 noname 0.0435 +46 H3 2.2252 6.3930 15.8058 H 1 noname 0.0435 +47 H4 1.2525 7.0408 13.7971 H 1 noname 0.0280 +48 H5 2.8643 7.6709 13.3892 H 1 noname 0.0280 +49 H6 1.6387 5.7932 11.8246 H 1 noname 0.0286 +50 H7 3.3620 5.7503 11.9904 H 1 noname 0.0286 +51 H8 1.2053 4.1406 13.6224 H 1 noname 0.0544 +52 H9 -0.3100 1.9001 13.9868 H 1 noname 0.0279 +53 H10 -0.7873 2.9493 12.6090 H 1 noname 0.0279 +54 H11 -1.2325 1.2091 12.6090 H 1 noname 0.0279 +55 H12 0.9838 -0.2277 11.2445 H 1 noname 0.1344 +56 H13 -0.3218 -0.3303 8.5254 H 1 noname 0.0509 +57 H14 0.5197 1.5950 7.1255 H 1 noname 0.0951 +58 H15 2.1713 1.3474 7.7334 H 1 noname 0.0951 +59 H16 0.6024 -0.8334 6.4630 H 1 noname 0.2583 +60 H17 1.7378 1.5740 5.2387 H 1 noname 0.0902 +61 H18 2.3891 0.0637 4.5165 H 1 noname 0.0902 +62 H19 0.6188 0.3686 4.5165 H 1 noname 0.0902 +63 H20 3.3925 -0.9098 6.4989 H 1 noname 0.1037 +64 H21 1.3537 -2.9679 5.9040 H 1 noname 0.0390 +65 H22 2.6362 -2.2149 4.8517 H 1 noname 0.0390 +66 H23 4.0630 -4.9434 4.7393 H 1 noname 0.0792 +67 H24 5.4996 -5.9893 6.7732 H 1 noname 0.1522 +68 H25 5.5571 -5.6516 9.6144 H 1 noname 0.0642 +69 H26 4.8229 -4.0061 11.4050 H 1 noname 0.0623 +70 H27 3.4662 -2.0466 10.8620 H 1 noname 0.0629 +71 H28 1.5745 -1.2472 10.2862 H 1 noname 0.0592 +72 H29 4.6215 2.8306 12.9273 H 1 noname 0.2151 +73 H30 4.8172 1.2403 14.5040 H 1 noname 0.0337 +74 H31 5.0109 2.7035 15.6340 H 1 noname 0.0337 +75 H32 4.1876 -0.9136 15.5298 H 1 noname 0.0625 +76 H33 3.9418 -2.2368 17.6433 H 1 noname 0.0622 +77 H34 4.5651 -1.2449 19.8993 H 1 noname 0.0622 +78 H35 5.2611 1.1659 19.9633 H 1 noname 0.0622 +79 H36 5.2166 2.5491 17.9195 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 3.9540 2.2580 14.5170 C.3 1 noname 0.2017 +2 C2 2.5960 2.5300 13.7710 C.2 1 noname 0.0859 +3 C3 1.5240 1.6550 11.7790 C.3 1 noname 0.1001 +4 O1 4.7920 1.8540 13.4020 O.3 1 noname -0.3049 +5 C4 1.7140 0.1870 11.1800 C.2 1 noname 0.0539 +6 C5 3.2850 -1.5800 10.3790 C.3 1 noname 0.0065 +7 C6 4.6870 -1.8630 10.8560 C.3 1 noname -0.0381 +8 C7 5.2520 -0.5490 11.3730 C.3 1 noname -0.0291 +9 C8 3.9140 0.1460 11.8950 C.3 1 noname 0.0870 +10 C9 3.9980 1.6780 12.1910 C.3 1 noname 0.2535 +11 C10 3.4260 1.1370 15.4310 C.3 1 noname -0.0125 +12 O2 1.5280 2.9700 14.2720 O.2 1 noname -0.2735 +13 N1 2.7070 2.1340 12.4360 N.3 1 noname -0.0076 +14 O3 0.6680 -0.3990 10.9100 O.2 1 noname -0.2883 +15 N2 2.9480 -0.2500 10.9680 N.3 1 noname -0.0572 +16 N3 4.6100 3.2950 15.1070 N.3 1 noname -0.0502 +17 C11 4.2380 3.8480 16.3400 C.2 1 noname 0.0544 +18 O4 3.2310 3.4690 16.9010 O.2 1 noname -0.2899 +19 C12 5.2160 4.8740 16.8650 C.3 1 noname 0.0996 +20 C13 4.4230 5.7900 17.8250 C.3 1 noname 0.0041 +21 N4 5.3900 6.7670 18.3850 N.4 1 noname 0.0094 +22 C14 4.5550 7.9670 18.9650 C.3 1 noname -0.0218 +23 C15 6.4730 6.2460 19.2050 C.3 1 noname 0.0303 +24 C16 7.6540 7.2120 19.5130 C.3 1 noname 0.0498 +25 C17 6.8650 4.8240 18.6260 C.2 1 noname -0.0158 +26 C18 8.7870 6.5360 20.3450 C.2 1 noname -0.0271 +27 C19 9.7460 6.8780 21.1840 C.2 1 noname -0.1133 +28 C20 8.7840 5.0960 20.1660 C.2 1 noname -0.0193 +29 N5 10.4340 5.6470 21.5430 N.3 1 noname -0.0790 +30 C21 9.8970 4.5700 20.8590 C.2 1 noname -0.0845 +31 C22 10.2260 3.2650 20.7820 C.2 1 noname -0.0420 +32 C23 9.3720 2.3830 20.0130 C.2 1 noname -0.0462 +33 C24 8.2810 2.8160 19.3610 C.2 1 noname -0.0383 +34 C25 8.0260 4.2370 19.3820 C.2 1 noname -0.0179 +35 C26 6.3510 4.2070 17.5780 C.2 1 noname -0.0320 +36 O5 4.4730 2.5520 11.2230 O.3 1 noname -0.3514 +37 C27 1.1060 2.5710 10.6220 C.3 1 noname -0.0030 +38 C28 0.4240 3.8360 10.9650 C.2 1 noname -0.0541 +39 C29 -0.8070 4.1270 10.4330 C.2 1 noname -0.0567 +40 C30 -1.3000 5.4590 10.4860 C.2 1 noname -0.0604 +41 C31 -0.6000 6.5070 11.1660 C.2 1 noname -0.0616 +42 C32 0.6280 6.1710 11.7350 C.2 1 noname -0.0604 +43 C33 1.1590 4.8920 11.6120 C.2 1 noname -0.0567 +44 H1 0.7469 1.6416 12.5575 H 1 noname 0.0574 +45 H2 3.2496 -1.5384 9.2804 H 1 noname 0.0435 +46 H3 2.5748 -2.3630 10.6833 H 1 noname 0.0435 +47 H4 4.6683 -2.6102 11.6630 H 1 noname 0.0280 +48 H5 5.3067 -2.2641 10.0405 H 1 noname 0.0280 +49 H6 5.9734 -0.7081 12.1880 H 1 noname 0.0286 +50 H7 5.8167 0.0348 10.6311 H 1 noname 0.0286 +51 H8 3.6596 -0.1855 12.9125 H 1 noname 0.0544 +52 H9 3.5626 1.4270 16.4833 H 1 noname 0.0279 +53 H10 2.3566 0.9743 15.2314 H 1 noname 0.0279 +54 H11 3.9816 0.2089 15.2314 H 1 noname 0.0279 +55 H12 5.4247 3.6953 14.6203 H 1 noname 0.1344 +56 H13 5.6566 5.4569 16.0428 H 1 noname 0.0509 +57 H14 3.6285 6.3164 17.2757 H 1 noname 0.0951 +58 H15 3.9469 5.2041 18.6251 H 1 noname 0.0951 +59 H16 5.9906 7.1144 17.6238 H 1 noname 0.2583 +60 H17 4.5788 7.9328 20.0642 H 1 noname 0.0902 +61 H18 4.9883 8.9167 18.6182 H 1 noname 0.0902 +62 H19 3.5139 7.8907 18.6182 H 1 noname 0.0902 +63 H20 6.1043 6.1314 20.2350 H 1 noname 0.1037 +64 H21 8.0787 7.5626 18.5608 H 1 noname 0.0390 +65 H22 7.2541 8.0432 20.1123 H 1 noname 0.0390 +66 H23 9.9791 7.8920 21.5411 H 1 noname 0.0792 +67 H24 11.2133 5.5855 22.2137 H 1 noname 0.1522 +68 H25 11.1216 2.8791 21.2909 H 1 noname 0.0642 +69 H26 9.6279 1.3144 19.9611 H 1 noname 0.0623 +70 H27 7.6117 2.1196 18.8346 H 1 noname 0.0629 +71 H28 6.7432 3.2363 17.2404 H 1 noname 0.0592 +72 H29 4.8968 3.3317 11.6618 H 1 noname 0.2151 +73 H30 2.0162 2.8292 10.0609 H 1 noname 0.0337 +74 H31 0.3566 1.9916 10.0628 H 1 noname 0.0337 +75 H32 -1.4095 3.3330 9.9676 H 1 noname 0.0625 +76 H33 -2.2522 5.6930 9.9874 H 1 noname 0.0622 +77 H34 -1.0101 7.5253 11.2359 H 1 noname 0.0622 +78 H35 1.1890 6.9348 12.2935 H 1 noname 0.0622 +79 H36 2.1601 4.6826 12.0168 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 3.4020 2.8100 13.6140 C.3 1 noname 0.2017 +2 C2 4.0190 1.7900 12.5890 C.2 1 noname 0.0859 +3 C3 3.1540 0.4630 10.7530 C.3 1 noname 0.1001 +4 O1 2.0450 2.3030 13.7090 O.3 1 noname -0.3049 +5 C4 1.9040 0.8380 9.8320 C.2 1 noname 0.0539 +6 C5 -0.5020 1.4880 9.7020 C.3 1 noname 0.0065 +7 C6 -1.2990 2.3070 10.6870 C.3 1 noname -0.0381 +8 C7 -0.6610 2.1010 12.0510 C.3 1 noname -0.0291 +9 C8 0.8580 1.8700 11.6190 C.3 1 noname 0.0870 +10 C9 1.8050 1.2690 12.7080 C.3 1 noname 0.2535 +11 C10 3.6140 4.0690 12.7530 C.3 1 noname -0.0125 +12 O2 5.2140 1.7380 12.1930 O.2 1 noname -0.2735 +13 N1 3.0130 0.9580 12.0930 N.3 1 noname -0.0076 +14 O3 2.1050 0.7410 8.6240 O.2 1 noname -0.2883 +15 N2 0.7610 1.1540 10.4250 N.3 1 noname -0.0572 +16 N3 3.8690 2.8360 14.8930 N.3 1 noname -0.0502 +17 C11 3.1930 3.4530 15.9540 C.2 1 noname 0.0544 +18 O4 2.1770 4.0840 15.7470 O.2 1 noname -0.2899 +19 C12 3.8260 3.2060 17.3040 C.3 1 noname 0.0996 +20 C13 4.5270 1.8310 17.2180 C.3 1 noname 0.0041 +21 N4 5.1960 1.6070 18.5240 N.4 1 noname 0.0094 +22 C14 5.4950 0.0660 18.6360 C.3 1 noname -0.0218 +23 C15 6.2600 2.5240 18.9010 C.3 1 noname 0.0303 +24 C16 6.7270 2.4940 20.3850 C.3 1 noname 0.0498 +25 C17 5.8880 3.9480 18.3140 C.2 1 noname -0.0158 +26 C18 7.8260 3.5560 20.6960 C.2 1 noname -0.0271 +27 C19 8.8150 3.7470 21.5470 C.2 1 noname -0.1133 +28 C20 7.7650 4.6650 19.7610 C.2 1 noname -0.0193 +29 N5 9.4040 5.0350 21.2100 N.3 1 noname -0.0790 +30 C21 8.7110 5.6300 20.1710 C.2 1 noname -0.0845 +31 C22 8.8070 6.8300 19.5620 C.2 1 noname -0.0420 +32 C23 7.9490 7.0960 18.4240 C.2 1 noname -0.0462 +33 C24 7.0550 6.2060 17.9670 C.2 1 noname -0.0383 +34 C25 6.9110 4.9770 18.7120 C.2 1 noname -0.0179 +35 C26 4.8080 4.2870 17.6340 C.2 1 noname -0.0320 +36 O5 1.4620 0.0950 13.3620 O.3 1 noname -0.3514 +37 C27 3.3020 -1.0630 10.7230 C.3 1 noname -0.0030 +38 C28 4.4930 -1.6450 11.3760 C.2 1 noname -0.0541 +39 C29 5.3070 -2.5110 10.6900 C.2 1 noname -0.0567 +40 C30 6.2340 -3.3200 11.4010 C.2 1 noname -0.0604 +41 C31 6.4260 -3.2000 12.8160 C.2 1 noname -0.0616 +42 C32 5.6150 -2.2800 13.4800 C.2 1 noname -0.0604 +43 C33 4.6450 -1.5480 12.8050 C.2 1 noname -0.0567 +44 H1 4.0626 0.9444 10.3622 H 1 noname 0.0574 +45 H2 -1.0464 0.5723 9.4280 H 1 noname 0.0435 +46 H3 -0.3146 2.0304 8.7636 H 1 noname 0.0435 +47 H4 -1.2641 3.3710 10.4099 H 1 noname 0.0280 +48 H5 -2.3541 1.9959 10.6949 H 1 noname 0.0280 +49 H6 -0.7722 2.9885 12.6912 H 1 noname 0.0286 +50 H7 -1.1000 1.2882 12.6482 H 1 noname 0.0286 +51 H8 1.3851 2.8250 11.4773 H 1 noname 0.0544 +52 H9 3.7608 4.9406 13.4078 H 1 noname 0.0279 +53 H10 4.5020 3.9337 12.1181 H 1 noname 0.0279 +54 H11 2.7307 4.2320 12.1181 H 1 noname 0.0279 +55 H12 4.7692 2.3765 15.0915 H 1 noname 0.1344 +56 H13 3.0693 3.2105 18.1023 H 1 noname 0.0509 +57 H14 3.7862 1.0395 17.0315 H 1 noname 0.0951 +58 H15 5.2549 1.8105 16.3935 H 1 noname 0.0951 +59 H16 4.5494 1.8785 19.2784 H 1 noname 0.2583 +60 H17 5.5506 -0.2206 19.6966 H 1 noname 0.0902 +61 H18 4.6900 -0.5003 18.1449 H 1 noname 0.0902 +62 H19 6.4534 -0.1582 18.1449 H 1 noname 0.0902 +63 H20 7.1977 2.1737 18.4449 H 1 noname 0.1037 +64 H21 5.8579 2.6886 21.0306 H 1 noname 0.0390 +65 H22 7.1630 1.5020 20.5743 H 1 noname 0.0390 +66 H23 9.1321 3.0677 22.3520 H 1 noname 0.0792 +67 H24 10.2231 5.4462 21.6800 H 1 noname 0.1522 +68 H25 9.5190 7.5882 19.9202 H 1 noname 0.0642 +69 H26 8.0345 8.0671 17.9145 H 1 noname 0.0623 +70 H27 6.4579 6.4036 17.0645 H 1 noname 0.0629 +71 H28 4.6358 5.3273 17.3209 H 1 noname 0.0592 +72 H29 1.5038 0.2381 14.3407 H 1 noname 0.2151 +73 H30 2.4151 -1.4900 11.2140 H 1 noname 0.0337 +74 H31 3.4156 -1.3131 9.6578 H 1 noname 0.0337 +75 H32 5.2422 -2.5787 9.5940 H 1 noname 0.0625 +76 H33 6.8245 -4.0639 10.8461 H 1 noname 0.0622 +77 H34 7.1747 -3.8026 13.3511 H 1 noname 0.0622 +78 H35 5.7458 -2.1303 14.5619 H 1 noname 0.0622 +79 H36 3.9801 -0.8812 13.3737 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 +@MOLECULE + +79 86 1 +SMALL +USER_CHARGES +@ATOM +1 C1 -2.3500 -7.2670 13.4620 C.3 1 noname 0.2017 +2 C2 -2.3550 -6.4140 14.7830 C.2 1 noname 0.0859 +3 C3 -3.8670 -6.1670 16.6630 C.3 1 noname 0.1001 +4 O1 -3.7760 -7.3940 13.2220 O.3 1 noname -0.3049 +5 C4 -4.8570 -7.2880 17.2240 C.2 1 noname 0.0539 +6 C5 -6.6810 -8.9230 16.7470 C.3 1 noname 0.0065 +7 C6 -6.9310 -9.6920 15.4740 C.3 1 noname -0.0381 +8 C7 -6.3700 -8.8570 14.3350 C.3 1 noname -0.0291 +9 C8 -5.1700 -8.1230 15.0890 C.3 1 noname 0.0870 +10 C9 -4.5410 -6.8930 14.3590 C.3 1 noname 0.2535 +11 C10 -1.6340 -8.4960 14.0530 C.3 1 noname -0.0125 +12 O2 -1.3550 -5.9640 15.4010 O.2 1 noname -0.2735 +13 N1 -3.6650 -6.2760 15.2460 N.3 1 noname -0.0076 +14 O3 -4.8090 -7.4580 18.4400 O.2 1 noname -0.2883 +15 N2 -5.6740 -7.8870 16.3690 N.3 1 noname -0.0572 +16 N3 -1.8370 -6.7280 12.3210 N.3 1 noname -0.0502 +17 C11 -2.3740 -6.9520 11.0460 C.2 1 noname 0.0544 +18 O4 -3.2920 -7.7330 10.8990 O.2 1 noname -0.2899 +19 C12 -1.7350 -6.1160 9.9620 C.3 1 noname 0.0996 +20 C13 -1.8770 -4.6410 10.4000 C.3 1 noname 0.0041 +21 N4 -1.2030 -3.8180 9.3640 N.4 1 noname 0.0094 +22 C14 -1.7330 -2.3450 9.5240 C.3 1 noname -0.0218 +23 C15 0.2290 -4.0000 9.1880 C.3 1 noname 0.0303 +24 C16 0.8650 -3.3930 7.9040 C.3 1 noname 0.0498 +25 C17 0.5530 -5.5230 9.4750 C.2 1 noname -0.0158 +26 C18 2.3900 -3.6960 7.7820 C.2 1 noname -0.0271 +27 C19 3.4670 -3.1840 7.2180 C.2 1 noname -0.1133 +28 C20 2.7500 -4.8910 8.5250 C.2 1 noname -0.0193 +29 N5 4.5680 -4.0760 7.5490 N.3 1 noname -0.0790 +30 C21 4.1140 -5.1610 8.2790 C.2 1 noname -0.0845 +31 C22 4.7090 -6.2780 8.7430 C.2 1 noname -0.0420 +32 C23 3.9290 -7.1850 9.5620 C.2 1 noname -0.0462 +33 C24 2.6390 -6.9660 9.8590 C.2 1 noname -0.0383 +34 C25 2.0130 -5.8140 9.2540 C.2 1 noname -0.0179 +35 C26 -0.2950 -6.4860 9.7880 C.2 1 noname -0.0320 +36 O5 -5.3470 -5.8520 13.9220 O.3 1 noname -0.3514 +37 C27 -4.4520 -4.8040 17.0520 C.3 1 noname -0.0030 +38 C28 -4.1710 -4.3060 18.4150 C.2 1 noname -0.0541 +39 C29 -2.8980 -4.3590 18.9240 C.2 1 noname -0.0567 +40 C30 -2.6920 -4.2040 20.3220 C.2 1 noname -0.0604 +41 C31 -3.7610 -3.8940 21.2230 C.2 1 noname -0.0616 +42 C32 -5.0380 -3.8020 20.6690 C.2 1 noname -0.0604 +43 C33 -5.2610 -4.0390 19.3170 C.2 1 noname -0.0567 +44 H1 -2.8686 -6.2959 17.1064 H 1 noname 0.0574 +45 H2 -7.6083 -8.4513 17.1043 H 1 noname 0.0435 +46 H3 -6.3276 -9.5704 17.5631 H 1 noname 0.0435 +47 H4 -6.4221 -10.6663 15.5148 H 1 noname 0.0280 +48 H5 -8.0057 -9.8790 15.3322 H 1 noname 0.0280 +49 H6 -6.0080 -9.4860 13.5084 H 1 noname 0.0286 +50 H7 -7.0953 -8.1831 13.8556 H 1 noname 0.0286 +51 H8 -4.2686 -8.7528 15.1176 H 1 noname 0.0544 +52 H9 -1.6639 -8.4447 15.1514 H 1 noname 0.0279 +53 H10 -2.1394 -9.4126 13.7148 H 1 noname 0.0279 +54 H11 -0.5873 -8.5084 13.7148 H 1 noname 0.0279 +55 H12 -1.0080 -6.1218 12.3997 H 1 noname 0.1344 +56 H13 -2.2252 -6.2849 8.9919 H 1 noname 0.0509 +57 H14 -2.9402 -4.3671 10.4684 H 1 noname 0.0951 +58 H15 -1.4242 -4.4781 11.3891 H 1 noname 0.0951 +59 H16 -1.4692 -4.1701 8.4334 H 1 noname 0.2583 +60 H17 -1.8208 -2.1010 10.5930 H 1 noname 0.0902 +61 H18 -1.0292 -1.6481 9.0454 H 1 noname 0.0902 +62 H19 -2.7195 -2.2562 9.0454 H 1 noname 0.0902 +63 H20 0.7517 -3.3713 9.9239 H 1 noname 0.1037 +64 H21 0.3522 -3.8127 7.0260 H 1 noname 0.0390 +65 H22 0.7486 -2.3007 7.9620 H 1 noname 0.0390 +66 H23 3.5219 -2.2647 6.6165 H 1 noname 0.0792 +67 H24 5.5495 -3.9214 7.2776 H 1 noname 0.1522 +68 H25 5.7608 -6.4960 8.5060 H 1 noname 0.0642 +69 H26 4.4147 -8.0899 9.9561 H 1 noname 0.0623 +70 H27 2.0832 -7.6342 10.5332 H 1 noname 0.0629 +71 H28 0.0452 -7.5242 9.9164 H 1 noname 0.0592 +72 H29 -5.7188 -5.3719 14.7039 H 1 noname 0.2151 +73 H30 -4.0586 -4.0616 16.3421 H 1 noname 0.0337 +74 H31 -5.5422 -4.9483 17.0250 H 1 noname 0.0337 +75 H32 -2.0410 -4.5206 18.2536 H 1 noname 0.0625 +76 H33 -1.6761 -4.3264 20.7257 H 1 noname 0.0622 +77 H34 -3.5842 -3.7364 22.2972 H 1 noname 0.0622 +78 H35 -5.8871 -3.5362 21.3158 H 1 noname 0.0622 +79 H36 -6.2902 -4.0222 18.9291 H 1 noname 0.0625 +@BOND +1 1 2 1 +2 1 4 1 +3 1 11 1 +4 1 16 1 +5 2 12 2 +6 2 13 1 +7 3 5 1 +8 3 13 1 +9 3 37 1 +10 4 10 1 +11 5 14 2 +12 5 15 1 +13 6 7 1 +14 6 15 1 +15 7 8 1 +16 8 9 1 +17 9 10 1 +18 9 15 1 +19 10 13 1 +20 10 36 1 +21 16 17 1 +22 17 18 2 +23 17 19 1 +24 19 20 1 +25 19 35 1 +26 20 21 1 +27 21 22 1 +28 21 23 1 +29 23 24 1 +30 23 25 1 +31 24 26 1 +32 25 34 1 +33 25 35 2 +34 26 27 2 +35 26 28 1 +36 27 29 1 +37 28 30 2 +38 28 34 1 +39 29 30 1 +40 30 31 1 +41 31 32 2 +42 32 33 1 +43 33 34 2 +44 37 38 1 +45 38 39 2 +46 38 43 1 +47 39 40 1 +48 40 41 2 +49 41 42 1 +50 42 43 2 +51 3 44 1 +52 6 45 1 +53 6 46 1 +54 7 47 1 +55 7 48 1 +56 8 49 1 +57 8 50 1 +58 9 51 1 +59 11 52 1 +60 11 53 1 +61 11 54 1 +62 16 55 1 +63 19 56 1 +64 20 57 1 +65 20 58 1 +66 21 59 1 +67 22 60 1 +68 22 61 1 +69 22 62 1 +70 23 63 1 +71 24 64 1 +72 24 65 1 +73 27 66 1 +74 29 67 1 +75 31 68 1 +76 32 69 1 +77 33 70 1 +78 35 71 1 +79 36 72 1 +80 37 73 1 +81 37 74 1 +82 39 75 1 +83 40 76 1 +84 41 77 1 +85 42 78 1 +86 43 79 1 +@SUBSTRUCTURE +1 noname 1 diff --git a/prolif/data/vina/vina_output.sdf b/prolif/data/vina/vina_output.sdf new file mode 100644 index 0000000..0d217b5 --- /dev/null +++ b/prolif/data/vina/vina_output.sdf @@ -0,0 +1,1547 @@ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 1.4240 1.3400 12.7270 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.4870 0.8460 13.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0730 1.9290 15.2560 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.0390 2.5820 12.2920 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9120 3.3800 15.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4980 5.8160 15.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6560 6.4710 14.4840 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6580 5.5380 13.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7950 4.1300 14.0210 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.1900 2.9120 13.1250 C 0 0 1 0 0 0 0 0 0 0 0 0 + 0.2490 1.4570 13.7150 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4730 -0.2350 14.4210 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4540 1.8360 13.9640 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1160 3.4310 17.1140 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6390 4.3990 15.1010 N 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2210 0.6180 11.5910 N 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6920 1.1580 10.4110 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3000 2.3070 10.3880 O 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7180 0.2040 9.2400 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.2190 1.0110 8.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2970 0.0640 6.8800 N 0 0 1 0 0 4 0 0 0 0 0 0 + 1.3330 0.9250 5.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2380 -1.0390 6.9860 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.0880 -2.1970 5.9570 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3040 -1.4620 8.5110 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1050 -3.3550 6.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7040 -4.3130 5.5140 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5500 -3.3880 7.5780 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5340 -5.0360 6.4660 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3780 -4.5210 7.7400 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8510 -4.8830 8.9500 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5410 -4.0450 10.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7890 -2.9380 9.9940 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2150 -2.6450 8.7010 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6230 -0.9550 9.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3150 2.9760 12.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5740 1.6220 15.1920 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.9870 0.3810 14.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.4950 0.4310 13.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.5700 -0.7570 12.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.2220 -2.0410 12.9850 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7500 -2.0670 14.2970 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5910 -0.8980 15.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5551 1.1833 15.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4828 6.3011 15.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0421 5.8939 16.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6284 6.6150 14.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0594 7.4586 14.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7214 5.6086 12.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4394 5.7466 12.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8162 3.7547 14.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6314 1.4189 14.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.2730 2.4116 13.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.4509 0.6241 13.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4702 -0.3814 11.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.2819 -0.2125 9.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.5151 1.8242 7.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2005 1.4640 8.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4494 -0.5211 6.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3776 1.9926 5.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2206 0.6547 4.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4259 0.7298 4.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2277 -0.6832 6.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0687 -2.6037 6.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2895 -1.7807 4.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5972 -4.5232 4.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1527 -5.8232 6.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4578 -5.7929 9.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9384 -4.3280 11.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6172 -2.2826 10.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7172 -1.3697 10.5365 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1264 3.0222 12.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.0608 2.4630 14.6765 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8754 1.4751 16.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.8427 1.3869 12.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.9068 -0.6885 11.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.3221 -2.9599 12.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4980 -3.0329 14.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1542 -0.9514 16.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 6 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 1.1200 1.1530 12.1940 C 0 0 2 0 0 0 0 0 0 0 0 0 + 1.8960 1.0940 13.5610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.9250 2.7320 15.0240 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.7240 2.3310 11.5960 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4720 4.2550 15.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9680 6.4400 14.0980 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3950 6.6810 12.7240 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8010 5.4980 11.8610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8500 4.3480 12.9660 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.5740 3.0240 12.5580 C 0 0 1 0 0 0 0 0 0 0 0 0 + -0.2840 1.3250 12.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7980 0.2120 14.4540 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6890 2.2350 13.6980 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3360 4.6270 16.3560 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3440 4.9950 14.1010 N 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2950 0.1540 11.2840 N 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0100 0.2900 9.9190 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4970 1.3070 9.5000 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4410 -0.8960 9.0880 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.8070 -1.3550 9.6470 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2100 -2.5530 8.8680 N 0 0 1 0 0 4 0 0 0 0 0 0 + 4.7580 -2.7440 9.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3700 -3.7350 8.9710 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.6000 -4.8600 7.9200 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.8750 -3.2410 9.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6080 -6.0520 8.0820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5470 -7.3420 7.8120 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3870 -5.6340 8.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2380 -7.7940 8.2610 N 0 0 0 0 0 0 0 0 0 0 0 0 + -0.4990 -6.7340 8.7590 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.7650 -6.6190 9.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.1920 -5.3410 9.7450 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3850 -4.2690 9.7930 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0740 -4.4070 9.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4310 -1.9980 9.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.8670 3.0610 12.0560 O 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4070 2.6500 15.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0700 1.3340 15.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8450 1.0410 14.2000 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1950 -0.3080 13.9250 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8470 -1.3830 14.8060 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0960 -1.0490 15.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6750 0.2560 16.1630 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3226 2.0893 15.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8526 7.0718 14.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2536 6.6869 14.8972 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2986 6.7504 12.7786 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7717 7.6239 12.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0526 5.2847 11.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7351 5.6367 11.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.8524 3.9204 13.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.2125 1.3162 13.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.7122 2.2823 12.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.9306 0.4994 12.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6566 -0.7508 11.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5245 -0.6239 8.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5533 -0.5561 9.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7358 -1.5879 10.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0258 -2.3782 7.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9820 -2.7716 10.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0771 -3.6883 8.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2970 -1.9056 8.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6768 -4.3014 9.8627 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4739 -4.4323 6.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6162 -5.2524 8.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3299 -7.9545 7.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0937 -8.7680 8.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.4564 -7.4738 9.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 + -3.2191 -5.2457 10.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.7080 -3.3274 10.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.6442 -1.7794 9.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5121 3.0795 12.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9541 3.3522 14.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4313 2.8830 16.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1943 1.8477 13.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.7523 -0.5351 13.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1566 -2.4190 14.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8305 -1.8354 16.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0279 0.4692 17.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 1.1630 1.1080 12.2000 C 0 0 2 0 0 0 0 0 0 0 0 0 + 1.8410 0.9760 13.6120 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8680 2.5190 15.1770 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.8760 2.2570 11.6690 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4990 4.0640 15.3490 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2040 6.2960 14.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7390 6.5980 12.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1290 5.4080 12.0100 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.0340 4.2370 13.0890 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.7010 2.8780 12.7000 C 0 0 1 0 0 0 0 0 0 0 0 0 + -0.2660 1.3570 12.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6290 0.0860 14.4770 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6910 2.0630 13.8270 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3080 4.4220 16.5090 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4890 4.8310 14.2680 N 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3370 0.1180 11.2810 N 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1390 0.2920 9.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7050 1.3430 9.4780 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5530 -0.9000 9.0750 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.9080 -1.3830 9.6410 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2940 -2.5880 8.8640 N 0 0 1 0 0 4 0 0 0 0 0 0 + 4.8370 -2.8060 9.0810 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4330 -3.7550 8.9620 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.6490 -4.8830 7.9120 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.9460 -3.2350 9.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6360 -6.0580 8.0680 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5540 -7.3470 7.7960 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4190 -5.6200 8.7260 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2350 -7.7760 8.2390 N 0 0 0 0 0 0 0 0 0 0 0 0 + -0.4860 -6.7040 8.7330 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.7530 -6.5660 9.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.1590 -5.2820 9.7110 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3350 -4.2240 9.7640 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0230 -4.3850 9.1810 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.5240 -1.9840 9.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0240 2.8430 12.2850 O 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3140 2.3380 15.6550 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5520 1.3830 16.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5630 0.0330 16.5160 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4520 -0.8780 17.6010 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4240 -0.4430 18.9660 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4590 0.9340 19.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4790 1.8360 18.1230 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1856 1.9029 15.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1129 6.8676 14.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4549 6.5726 15.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6476 6.7343 12.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1990 7.5236 12.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4227 5.2562 11.1805 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1055 5.4988 11.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0026 3.8687 13.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.2632 1.3565 13.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.6236 2.3310 12.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.9319 0.5614 12.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6305 -0.8106 11.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6464 -0.6290 8.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6688 -0.5973 9.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8272 -1.6147 10.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1179 -2.4099 7.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0550 -2.8368 10.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1418 -3.7561 8.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.3931 -1.9775 8.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7249 -4.3269 9.8551 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.5355 -4.4527 6.9060 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6575 -5.2929 8.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3281 -7.9727 7.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.1131 -8.7442 8.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.4599 -7.4077 9.1345 H 0 0 0 0 0 0 0 0 0 0 0 0 + -3.1859 -5.1695 10.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.6446 -3.2770 10.2303 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.5475 -1.7465 9.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6179 2.8273 13.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9067 1.9998 14.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5991 3.3180 16.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6573 -0.3429 15.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3852 -1.9546 17.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3773 -1.1587 19.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4711 1.3158 20.2145 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4383 2.9152 18.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 2.9670 0.4730 11.2610 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.7690 -0.9680 10.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8690 -1.8640 8.5980 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.8680 1.1780 10.6240 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8700 -1.1300 7.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2780 0.8990 5.8510 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2380 2.3330 6.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.9350 2.3090 7.8030 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6220 0.9270 8.2080 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.2370 0.3440 9.6060 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.3730 0.7100 10.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4330 -2.0020 10.9390 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7680 -0.9390 9.6910 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2820 -1.8140 6.2450 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3820 0.1000 7.1090 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7980 0.6710 12.5980 N 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6850 0.1930 13.5720 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6190 -0.5130 13.2530 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3740 0.6810 14.9680 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.5310 0.1990 15.8720 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2580 0.7210 17.2350 N 0 0 1 0 0 4 0 0 0 0 0 0 + 5.1240 -0.1260 18.2390 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2460 2.1640 17.4120 C 0 0 2 0 0 0 0 0 0 0 0 0 + 3.6450 2.7080 18.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6820 2.8020 16.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6250 4.2670 18.8030 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6280 5.2280 19.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6210 4.8460 17.4720 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5790 6.4830 18.9690 N 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4930 6.2460 17.6080 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3430 7.0510 16.5370 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3750 6.4540 15.2160 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5290 5.1350 15.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5780 4.2980 16.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2600 2.1730 14.9950 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0960 0.1670 9.9460 O 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7110 -2.8680 8.5930 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0450 -4.2960 8.7820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3360 -4.7320 8.6250 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.5970 -6.1200 8.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5640 -7.1080 8.5690 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2670 -6.6380 8.7730 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0090 -5.2760 8.8370 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8262 -2.3845 8.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3597 0.6422 5.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1146 0.7056 5.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2098 2.8158 6.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4725 2.9020 5.7660 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3940 3.1609 8.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.1322 2.3863 8.0583 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6989 1.0529 8.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0942 0.8316 11.5006 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6638 -0.1518 10.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3652 1.6195 10.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9723 1.2016 12.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4105 0.2838 15.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5663 -0.9003 15.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5003 0.5606 15.4982 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2610 0.5801 17.4520 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8527 0.1394 19.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9344 -1.1969 18.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1904 0.0873 18.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2808 2.5026 17.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6130 2.3393 18.8367 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2837 2.3524 19.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6610 5.1059 20.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6048 7.4178 19.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1998 8.1344 16.6623 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2688 7.1085 14.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6142 4.7102 14.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8391 2.7268 14.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.1863 0.1550 10.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.0224 -2.5809 9.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2939 -2.8098 7.5768 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1658 -4.0099 8.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6276 -6.4474 8.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7829 -8.1829 8.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.5555 -7.3597 8.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.0525 -4.9410 8.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 1 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 1 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 1 + 20 57 1 0 + 20 58 1 0 + 21 59 1 1 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 4.3630 3.0650 16.3440 C 0 0 2 0 0 0 0 0 0 0 0 0 + 5.3850 3.8250 17.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4210 5.9770 18.3830 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.6990 4.1860 15.7030 O 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1440 6.7850 18.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9120 7.7710 18.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.8860 7.2760 17.3920 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6430 6.5360 16.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8780 5.9790 17.1430 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.0960 5.4470 16.3210 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.5970 2.3610 17.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.2650 3.3140 18.0090 O 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1330 5.1970 17.2130 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2280 7.1920 20.0600 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1500 7.0010 18.0540 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8310 2.2910 15.3250 N 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1380 0.9300 15.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0810 0.3980 16.5510 O 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4800 0.2500 14.1570 C 0 0 1 0 0 0 0 0 0 0 0 0 + 5.7630 -1.2320 14.4910 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.0470 -1.9160 13.2040 N 0 0 1 0 0 4 0 0 0 0 0 0 + 6.7880 -3.2620 13.5470 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9750 -1.9730 12.2230 C 0 0 2 0 0 0 0 0 0 0 0 0 + 5.3650 -2.3890 10.7740 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1310 -0.6400 12.3640 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1560 -2.3580 9.7900 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7740 -2.9270 8.6620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1240 -1.4480 10.2520 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4780 -2.3530 8.3320 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1190 -1.3920 9.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0800 -0.5370 9.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.9770 0.2960 10.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.8810 0.2630 11.5270 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0320 -0.5880 11.3370 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3470 0.3720 13.1850 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6860 6.2450 15.3510 O 0 0 0 0 0 0 0 0 0 0 0 0 + 6.5350 6.9990 18.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.7390 6.9230 18.9820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.8380 6.2140 18.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.8420 5.8600 19.5110 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.8020 6.3000 20.8740 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.6940 7.0570 21.2530 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.6640 7.3340 20.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7376 5.2478 19.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.0821 8.8505 18.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5921 7.6257 19.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.1797 6.5955 17.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3083 8.1127 16.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.0432 5.7211 15.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9171 7.1506 15.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6237 5.0382 17.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9775 2.7107 18.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.5254 2.5960 17.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7409 1.2734 17.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9667 2.7300 14.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.3562 0.7184 13.6848 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.6320 -1.3098 15.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9040 -1.6923 15.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.6739 -1.3222 12.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.8516 -3.3775 14.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.2283 -4.1076 13.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.8019 -3.2413 13.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3351 -2.8363 12.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1361 -1.6966 10.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7323 -3.4251 10.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3256 -3.6845 8.0859 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9067 -2.6245 7.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3292 -0.4733 8.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.1227 0.9833 10.6241 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7511 0.8577 12.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7167 1.2730 13.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2142 6.9594 15.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.8624 6.8762 17.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.0825 7.9726 18.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.9419 5.9204 17.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 + 10.6787 5.2264 19.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 + 10.6043 6.0533 21.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.6334 7.4438 22.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.7752 7.8771 20.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 0.8590 1.6010 12.1830 C 0 0 2 0 0 0 0 0 0 0 0 0 + 1.6390 1.1340 13.4670 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0260 2.2280 15.1280 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.6830 2.7220 11.7660 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.9100 3.7520 15.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8510 6.1590 14.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3080 6.7620 13.6620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4340 5.7020 12.5790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2660 4.3820 13.4590 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.6840 3.0370 12.7790 C 0 0 1 0 0 0 0 0 0 0 0 0 + -0.4620 1.9390 12.8980 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3790 0.1400 14.1950 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6580 2.0440 13.7530 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8840 3.9220 16.8070 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.9130 4.6930 14.6560 N 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7960 0.7750 11.1020 N 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4900 1.2130 9.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.1720 2.3680 9.6120 O 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6450 0.1430 8.7520 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.2250 0.8380 7.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4290 -0.2190 6.4760 N 0 0 1 0 0 4 0 0 0 0 0 0 + 1.5530 0.5010 5.0820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3900 -1.2680 6.7760 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.3630 -2.5320 5.8690 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3370 -1.5270 8.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3900 -3.6180 6.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0720 -4.6180 5.7900 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7140 -3.4900 7.7220 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8390 -5.2060 6.8780 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5580 -4.5670 8.0730 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9360 -4.7830 9.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5040 -3.8430 10.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7310 -2.7820 10.0880 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2620 -2.6480 8.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5560 -0.9440 9.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9420 2.9030 12.2110 O 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4670 1.7770 15.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.7000 0.8970 16.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.3740 -0.4340 16.5020 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2780 -1.1910 17.7010 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6040 -0.6390 18.9820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9730 0.7050 19.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9850 1.4760 17.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3177 1.6104 15.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.8531 6.5554 15.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.2252 6.3930 15.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2525 7.0408 13.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.8643 7.6709 13.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.6387 5.7932 11.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3620 5.7503 11.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2053 4.1406 13.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.3100 1.9001 13.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.7873 2.9493 12.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.2325 1.2091 12.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.9838 -0.2277 11.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.3218 -0.3303 8.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.5197 1.5950 7.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1713 1.3474 7.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6024 -0.8334 6.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7378 1.5740 5.2387 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3891 0.0637 4.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6188 0.3686 4.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3925 -0.9098 6.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3537 -2.9679 5.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6362 -2.2149 4.8517 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0630 -4.9434 4.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4996 -5.9893 6.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5571 -5.6516 9.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8229 -4.0061 11.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4662 -2.0466 10.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5745 -1.2472 10.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6215 2.8306 12.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8172 1.2403 14.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.0109 2.7035 15.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1876 -0.9136 15.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9418 -2.2368 17.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5651 -1.2449 19.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2611 1.1659 19.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2166 2.5491 17.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 3.9540 2.2580 14.5170 C 0 0 2 0 0 0 0 0 0 0 0 0 + 2.5960 2.5300 13.7710 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5240 1.6550 11.7790 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.7920 1.8540 13.4020 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.7140 0.1870 11.1800 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2850 -1.5800 10.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6870 -1.8630 10.8560 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2520 -0.5490 11.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9140 0.1460 11.8950 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.9980 1.6780 12.1910 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.4260 1.1370 15.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5280 2.9700 14.2720 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7070 2.1340 12.4360 N 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6680 -0.3990 10.9100 O 0 0 0 0 0 0 0 0 0 0 0 0 + 2.9480 -0.2500 10.9680 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6100 3.2950 15.1070 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.2380 3.8480 16.3400 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2310 3.4690 16.9010 O 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2160 4.8740 16.8650 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.4230 5.7900 17.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.3900 6.7670 18.3850 N 0 0 1 0 0 4 0 0 0 0 0 0 + 4.5550 7.9670 18.9650 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.4730 6.2460 19.2050 C 0 0 2 0 0 0 0 0 0 0 0 0 + 7.6540 7.2120 19.5130 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.8650 4.8240 18.6260 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.7870 6.5360 20.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.7460 6.8780 21.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.7840 5.0960 20.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 + 10.4340 5.6470 21.5430 N 0 0 0 0 0 0 0 0 0 0 0 0 + 9.8970 4.5700 20.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 + 10.2260 3.2650 20.7820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.3720 2.3830 20.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.2810 2.8160 19.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.0260 4.2370 19.3820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.3510 4.2070 17.5780 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4730 2.5520 11.2230 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1060 2.5710 10.6220 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.4240 3.8360 10.9650 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.8070 4.1270 10.4330 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3000 5.4590 10.4860 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.6000 6.5070 11.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.6280 6.1710 11.7350 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1590 4.8920 11.6120 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7469 1.6416 12.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.2496 -1.5384 9.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.5748 -2.3630 10.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6683 -2.6102 11.6630 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.3067 -2.2641 10.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.9734 -0.7081 12.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8167 0.0348 10.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6596 -0.1855 12.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5626 1.4270 16.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3566 0.9743 15.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9816 0.2089 15.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.4247 3.6953 14.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.6566 5.4569 16.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6285 6.3164 17.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9469 5.2041 18.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.9906 7.1144 17.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5788 7.9328 20.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.9883 8.9167 18.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5139 7.8907 18.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.1043 6.1314 20.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.0787 7.5626 18.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.2541 8.0432 20.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 + 9.9791 7.8920 21.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 + 11.2133 5.5855 22.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 + 11.1216 2.8791 21.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 + 9.6279 1.3144 19.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.6117 2.1196 18.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.7432 3.2363 17.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8968 3.3317 11.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.0162 2.8292 10.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3566 1.9916 10.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.4095 3.3330 9.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.2522 5.6930 9.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.0101 7.5253 11.2359 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1890 6.9348 12.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1601 4.6826 12.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 1 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + 3.4020 2.8100 13.6140 C 0 0 2 0 0 0 0 0 0 0 0 0 + 4.0190 1.7900 12.5890 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1540 0.4630 10.7530 C 0 0 1 0 0 0 0 0 0 0 0 0 + 2.0450 2.3030 13.7090 O 0 0 0 0 0 0 0 0 0 0 0 0 + 1.9040 0.8380 9.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.5020 1.4880 9.7020 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.2990 2.3070 10.6870 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.6610 2.1010 12.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.8580 1.8700 11.6190 C 0 0 1 0 0 0 0 0 0 0 0 0 + 1.8050 1.2690 12.7080 C 0 0 1 0 0 0 0 0 0 0 0 0 + 3.6140 4.0690 12.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2140 1.7380 12.1930 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0130 0.9580 12.0930 N 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1050 0.7410 8.6240 O 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7610 1.1540 10.4250 N 0 0 0 0 0 0 0 0 0 0 0 0 + 3.8690 2.8360 14.8930 N 0 0 0 0 0 0 0 0 0 0 0 0 + 3.1930 3.4530 15.9540 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1770 4.0840 15.7470 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.8260 3.2060 17.3040 C 0 0 1 0 0 0 0 0 0 0 0 0 + 4.5270 1.8310 17.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.1960 1.6070 18.5240 N 0 0 1 0 0 4 0 0 0 0 0 0 + 5.4950 0.0660 18.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.2600 2.5240 18.9010 C 0 0 2 0 0 0 0 0 0 0 0 0 + 6.7270 2.4940 20.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8880 3.9480 18.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.8260 3.5560 20.6960 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.8150 3.7470 21.5470 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.7650 4.6650 19.7610 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.4040 5.0350 21.2100 N 0 0 0 0 0 0 0 0 0 0 0 0 + 8.7110 5.6300 20.1710 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.8070 6.8300 19.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.9490 7.0960 18.4240 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.0550 6.2060 17.9670 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.9110 4.9770 18.7120 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.8080 4.2870 17.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.4620 0.0950 13.3620 O 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3020 -1.0630 10.7230 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4930 -1.6450 11.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.3070 -2.5110 10.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.2340 -3.3200 11.4010 C 0 0 0 0 0 0 0 0 0 0 0 0 + 6.4260 -3.2000 12.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.6150 -2.2800 13.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6450 -1.5480 12.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.0626 0.9444 10.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.0464 0.5723 9.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.3146 2.0304 8.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.2641 3.3710 10.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.3541 1.9959 10.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.7722 2.9885 12.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.1000 1.2882 12.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3851 2.8250 11.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7608 4.9406 13.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5020 3.9337 12.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7307 4.2320 12.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.7692 2.3765 15.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0693 3.2105 18.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.7862 1.0395 17.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2549 1.8105 16.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5494 1.8785 19.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5506 -0.2206 19.6966 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6900 -0.5003 18.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.4534 -0.1582 18.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.1977 2.1737 18.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.8579 2.6886 21.0306 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.1630 1.5020 20.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 + 9.1321 3.0677 22.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 + 10.2231 5.4462 21.6800 H 0 0 0 0 0 0 0 0 0 0 0 0 + 9.5190 7.5882 19.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.0345 8.0671 17.9145 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.4579 6.4036 17.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.6358 5.3273 17.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.5038 0.2381 14.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.4151 -1.4900 11.2140 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4156 -1.3131 9.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.2422 -2.5787 9.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 + 6.8245 -4.0639 10.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 + 7.1747 -3.8026 13.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7458 -2.1303 14.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9801 -0.8812 13.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 1 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 1 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 6 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 6 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 1 + 20 57 1 0 + 20 58 1 0 + 21 59 1 1 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 6 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END +$$$$ + + RDKit 3D + + 79 86 0 0 0 0 0 0 0 0999 V2000 + -2.3500 -7.2670 13.4620 C 0 0 2 0 0 0 0 0 0 0 0 0 + -2.3550 -6.4140 14.7830 C 0 0 0 0 0 0 0 0 0 0 0 0 + -3.8670 -6.1670 16.6630 C 0 0 1 0 0 0 0 0 0 0 0 0 + -3.7760 -7.3940 13.2220 O 0 0 0 0 0 0 0 0 0 0 0 0 + -4.8570 -7.2880 17.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 + -6.6810 -8.9230 16.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 + -6.9310 -9.6920 15.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 + -6.3700 -8.8570 14.3350 C 0 0 0 0 0 0 0 0 0 0 0 0 + -5.1700 -8.1230 15.0890 C 0 0 1 0 0 0 0 0 0 0 0 0 + -4.5410 -6.8930 14.3590 C 0 0 1 0 0 0 0 0 0 0 0 0 + -1.6340 -8.4960 14.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3550 -5.9640 15.4010 O 0 0 0 0 0 0 0 0 0 0 0 0 + -3.6650 -6.2760 15.2460 N 0 0 0 0 0 0 0 0 0 0 0 0 + -4.8090 -7.4580 18.4400 O 0 0 0 0 0 0 0 0 0 0 0 0 + -5.6740 -7.8870 16.3690 N 0 0 0 0 0 0 0 0 0 0 0 0 + -1.8370 -6.7280 12.3210 N 0 0 0 0 0 0 0 0 0 0 0 0 + -2.3740 -6.9520 11.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 + -3.2920 -7.7330 10.8990 O 0 0 0 0 0 0 0 0 0 0 0 0 + -1.7350 -6.1160 9.9620 C 0 0 1 0 0 0 0 0 0 0 0 0 + -1.8770 -4.6410 10.4000 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.2030 -3.8180 9.3640 N 0 0 1 0 0 4 0 0 0 0 0 0 + -1.7330 -2.3450 9.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.2290 -4.0000 9.1880 C 0 0 2 0 0 0 0 0 0 0 0 0 + 0.8650 -3.3930 7.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.5530 -5.5230 9.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3900 -3.6960 7.7820 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.4670 -3.1840 7.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.7500 -4.8910 8.5250 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.5680 -4.0760 7.5490 N 0 0 0 0 0 0 0 0 0 0 0 0 + 4.1140 -5.1610 8.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.7090 -6.2780 8.7430 C 0 0 0 0 0 0 0 0 0 0 0 0 + 3.9290 -7.1850 9.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.6390 -6.9660 9.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.0130 -5.8140 9.2540 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.2950 -6.4860 9.7880 C 0 0 0 0 0 0 0 0 0 0 0 0 + -5.3470 -5.8520 13.9220 O 0 0 0 0 0 0 0 0 0 0 0 0 + -4.4520 -4.8040 17.0520 C 0 0 0 0 0 0 0 0 0 0 0 0 + -4.1710 -4.3060 18.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.8980 -4.3590 18.9240 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.6920 -4.2040 20.3220 C 0 0 0 0 0 0 0 0 0 0 0 0 + -3.7610 -3.8940 21.2230 C 0 0 0 0 0 0 0 0 0 0 0 0 + -5.0380 -3.8020 20.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 + -5.2610 -4.0390 19.3170 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.8686 -6.2959 17.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 + -7.6083 -8.4513 17.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 + -6.3276 -9.5704 17.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 + -6.4221 -10.6663 15.5148 H 0 0 0 0 0 0 0 0 0 0 0 0 + -8.0057 -9.8790 15.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 + -6.0080 -9.4860 13.5084 H 0 0 0 0 0 0 0 0 0 0 0 0 + -7.0953 -8.1831 13.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 + -4.2686 -8.7528 15.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.6639 -8.4447 15.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.1394 -9.4126 13.7148 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.5873 -8.5084 13.7148 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.0080 -6.1218 12.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.2252 -6.2849 8.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.9402 -4.3671 10.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.4242 -4.4781 11.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.4692 -4.1701 8.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.8208 -2.1010 10.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.0292 -1.6481 9.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.7195 -2.2562 9.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7517 -3.3713 9.9239 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.3522 -3.8127 7.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.7486 -2.3007 7.9620 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.5219 -2.2647 6.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5495 -3.9214 7.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7608 -6.4960 8.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 + 4.4147 -8.0899 9.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.0832 -7.6342 10.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 + 0.0452 -7.5242 9.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 + -5.7188 -5.3719 14.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 + -4.0586 -4.0616 16.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 + -5.5422 -4.9483 17.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.0410 -4.5206 18.2536 H 0 0 0 0 0 0 0 0 0 0 0 0 + -1.6761 -4.3264 20.7257 H 0 0 0 0 0 0 0 0 0 0 0 0 + -3.5842 -3.7364 22.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 + -5.8871 -3.5362 21.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 + -6.2902 -4.0222 18.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 2 1 0 + 1 4 1 0 + 1 11 1 0 + 1 16 1 6 + 2 12 2 0 + 2 13 1 0 + 3 5 1 0 + 3 13 1 0 + 3 37 1 0 + 4 10 1 0 + 5 14 2 0 + 5 15 1 0 + 6 7 1 0 + 6 15 1 0 + 7 8 1 0 + 8 9 1 0 + 9 10 1 0 + 9 15 1 0 + 10 13 1 0 + 10 36 1 6 + 16 17 1 0 + 17 18 2 0 + 17 19 1 0 + 19 20 1 0 + 19 35 1 0 + 20 21 1 0 + 21 22 1 0 + 21 23 1 0 + 23 24 1 0 + 23 25 1 0 + 24 26 1 0 + 25 34 1 0 + 25 35 2 0 + 26 27 2 0 + 26 28 1 0 + 27 29 1 0 + 28 30 2 0 + 28 34 1 0 + 29 30 1 0 + 30 31 1 0 + 31 32 2 0 + 32 33 1 0 + 33 34 2 0 + 37 38 1 0 + 38 39 2 0 + 38 43 1 0 + 39 40 1 0 + 40 41 2 0 + 41 42 1 0 + 42 43 2 0 + 3 44 1 1 + 6 45 1 0 + 6 46 1 0 + 7 47 1 0 + 7 48 1 0 + 8 49 1 0 + 8 50 1 0 + 9 51 1 1 + 11 52 1 0 + 11 53 1 0 + 11 54 1 0 + 16 55 1 0 + 19 56 1 6 + 20 57 1 0 + 20 58 1 0 + 21 59 1 6 + 22 60 1 0 + 22 61 1 0 + 22 62 1 0 + 23 63 1 1 + 24 64 1 0 + 24 65 1 0 + 27 66 1 0 + 29 67 1 0 + 31 68 1 0 + 32 69 1 0 + 33 70 1 0 + 35 71 1 0 + 36 72 1 0 + 37 73 1 0 + 37 74 1 0 + 39 75 1 0 + 40 76 1 0 + 41 77 1 0 + 42 78 1 0 + 43 79 1 0 +M CHG 1 21 1 +M END diff --git a/prolif/fingerprint.py b/prolif/fingerprint.py index a289f1c..fd85983 100644 --- a/prolif/fingerprint.py +++ b/prolif/fingerprint.py @@ -158,9 +158,12 @@ def list_available(show_hidden=False): underscore ``_``. Those are not supposed to be called directly) """ if show_hidden: - return [name for name in _INTERACTIONS.keys()] - return [name for name in _INTERACTIONS.keys() - if not (name.startswith("_") or name == "Interaction")] + interactions = [name for name in _INTERACTIONS.keys()] + else: + interactions = [name for name in _INTERACTIONS.keys() + if not (name.startswith("_") + or name == "Interaction")] + return sorted(interactions) @property def n_interactions(self): @@ -290,6 +293,74 @@ def run(self, traj, lig, prot, residues=None, return_atoms=False, self.ifp = ifp return self + def run_from_iterable(self, lig_iterable, prot_mol, residues=None, + return_atoms=False, progress=True): + """Generates the fingerprint between a list of ligands and a protein + + Parameters + ---------- + lig_iterable : list or generator + An iterable yielding ligands as :class:`~prolif.molecule.Molecule` + objects + prot_mol : prolif.molecule.Molecule + The protein + residues : list or "all" or None + A list of protein residues (:class:`str`, :class:`int` or + :class:`~prolif.residue.ResidueId`) to take into account for + the fingerprint extraction. + If ``"all"``, all residues will be used. + If ``None``, at each frame the :func:`~prolif.utils.get_residues_near_ligand` + function is used to automatically use protein residues that are + distant of 6.0 Å or less from each ligand residue. + return_atoms : bool + For each residue pair and interaction, return indices of atoms + responsible for the interaction instead of bits. + progress : bool + Use the `tqdm `_ package to display a + progressbar while running the calculation + + Returns + ------- + prolif.fingerprint.Fingerprint + The Fingerprint instance that generated the fingerprint + + Example + ------- + :: + + >>> prot = mda.Universe("protein.pdb") + >>> prot = plf.Molecule.from_mda(prot) + >>> lig_iter = plf.mol2_supplier("docking_output.mol2") + >>> fp = plf.Fingerprint() + >>> fp.run_from_iterable(lig_iter, prot) + + """ + iterator = tqdm(lig_iterable) if progress else lig_iterable + # set which residues to use + select_residues = False + if residues == "all": + resids = prot_mol.residues.keys() + elif isinstance(residues, Iterable): + resids = residues + else: + select_residues = True + ifp = [] + for i, lig_mol in enumerate(iterator): + data = {"Frame": i} + lres = lig_mol[0] + if select_residues: + resids = get_residues_near_ligand(lres, prot_mol) + for prot_key in resids: + pres = prot_mol[prot_key] + if return_atoms: + bv, value = self.bitvector_atoms(lres, pres) + else: + value = self.bitvector(lres, pres) + data[(lres.resid, pres.resid)] = value + ifp.append(data) + self.ifp = ifp + return self + def to_dataframe(self, **kwargs): """Converts fingerprints to a pandas DataFrame diff --git a/prolif/molecule.py b/prolif/molecule.py index 1bae60f..fe86cea 100644 --- a/prolif/molecule.py +++ b/prolif/molecule.py @@ -2,14 +2,17 @@ Reading proteins and ligands --- :mod:`prolif.molecule` ======================================================= """ +import copy from operator import attrgetter -from MDAnalysis import _CONVERTERS +import MDAnalysis as mda +from rdkit import Chem +from rdkit.Chem.AllChem import AssignBondOrdersFromTemplate from .rdkitmol import BaseRDKitMol from .residue import Residue, ResidueGroup from .utils import split_mol_by_residues -mda_to_rdkit = _CONVERTERS["RDKIT"]().convert +mda_to_rdkit = mda._CONVERTERS["RDKIT"]().convert class Molecule(BaseRDKitMol): @@ -78,7 +81,7 @@ def __init__(self, mol): @classmethod def from_mda(cls, obj, selection=None, **kwargs): - """Create a Molecule from an MDAnalysis object + """Creates a Molecule from an MDAnalysis object Parameters ---------- @@ -111,6 +114,42 @@ def from_mda(cls, obj, selection=None, **kwargs): ag = obj.select_atoms(selection) if selection else obj.atoms mol = mda_to_rdkit(ag, **kwargs) return cls(mol) + + @classmethod + def from_rdkit(cls, mol, resname="UNL", resnumber=1, chain=""): + """Creates a Molecule from an RDKit molecule + + While directly instantiating a molecule with ``prolif.Molecule(mol)`` + would also work, this method insures that every atom is linked to an + AtomPDBResidueInfo which is required by ProLIF + + Parameters + ---------- + mol : rdkit.Chem.rdchem.Mol + The input RDKit molecule + resname : str + The default residue name that is used if none was found + resnumber : int + The default residue number that is used if none was found + chain : str + The default chain Id that is used if none was found + + Notes + ----- + This method only checks for an existing AtomPDBResidueInfo in the first + atom. If none was found, it will patch all atoms with the one created + from the method's arguments (resname, resnumber, chain). + """ + if mol.GetAtomWithIdx(0).GetMonomerInfo(): + return cls(mol) + mol = copy.deepcopy(mol) + for atom in mol.GetAtoms(): + mi = Chem.AtomPDBResidueInfo(f" {atom.GetSymbol():<3.3}", + residueName=resname, + residueNumber=resnumber, + chainId=chain) + atom.SetMonomerInfo(mi) + return cls(mol) def __iter__(self): for residue in self.residues.values(): @@ -127,3 +166,124 @@ def __repr__(self): # pragma: no cover @property def n_residues(self): return len(self.residues) + + +def pdbqt_supplier(paths, template): + """Supplies molecules, given a path to PDBQT files + + Parameters + ---------- + paths : list + A list (or any iterable) of PDBQT files + template : rdkit.Chem.rdchem.Mol + A template molecule with the correct bond orders and charges. It must + match exactly the molecule inside the PDBQT file. + + Returns + ------- + suppl : generator + A generator object that will provide the :class:`Molecule` object as + you iterate over it. + + Example + ------- + The supplier is typically used like this:: + + >>> import glob + >>> pdbqts = glob.glob("docking/ligand1/*.pdbqt") + >>> lig_suppl = pdbqt_supplier(pdbqts, template) + >>> for lig in lig_suppl: + ... # do something with each ligand + + """ + for pdbqt_path in paths: + pdbqt = mda.Universe(pdbqt_path) + # set attributes needed by the converter + elements = [mda.topology.guessers.guess_atom_element(x) + for x in pdbqt.atoms.names] + pdbqt.add_TopologyAttr("elements", elements) + pdbqt.add_TopologyAttr("chainIDs", pdbqt.atoms.segids) + pdbqt.atoms.types = pdbqt.atoms.elements + # convert without infering bond orders and charges + mol = mda_to_rdkit(pdbqt.atoms, NoImplicit=False) + # assign BO from template then add hydrogens + mol = Chem.RemoveHs(mol, sanitize=False) + mol = AssignBondOrdersFromTemplate(template, mol) + mol = Chem.AddHs(mol, addCoords=True, addResidueInfo=True) + yield Molecule(mol) + + +def sdf_supplier(path, **kwargs): + """Supplies molecules, given a path to an SDFile + + Parameters + ---------- + path : str + A path to the .sdf file + resname : str + Residue name for every ligand + resnumber : int + Residue number for every ligand + chain : str + Chain ID for every ligand + + Returns + ------- + suppl : generator + A generator object that will provide the :class:`Molecule` object as + you iterate over it. + + Example + ------- + The supplier is typically used like this:: + + >>> lig_suppl = sdf_supplier("docking/output.sdf") + >>> for lig in lig_suppl: + ... # do something with each ligand + + """ + suppl = Chem.SDMolSupplier(path, removeHs=False) + for mol in suppl: + yield Molecule.from_rdkit(mol, **kwargs) + + +def mol2_supplier(path, **kwargs): + """Generates prolif.Molecule objects from a MOL2 file + + Parameters + ---------- + path : str + A path to the .mol2 file + resname : str + Residue name for every ligand + resnumber : int + Residue number for every ligand + chain : str + Chain ID for every ligand + + Returns + ------- + suppl : generator + A generator object that will provide the :class:`Molecule` object as + you iterate over it. + + Example + ------- + The supplier is typically used like this:: + + >>> lig_suppl = mol2_supplier("docking/output.mol2") + >>> for lig in lig_suppl: + ... # do something with each ligand + + """ + block = [] + with open(path, "r") as f: + for line in f: + if block and line.startswith("@MOLECULE"): + mol = Chem.MolFromMol2Block("".join(block), removeHs=False) + yield Molecule.from_rdkit(mol, **kwargs) + block = [] + block.append(line) + mol = Chem.MolFromMol2Block("".join(block), removeHs=False) + yield Molecule.from_rdkit(mol, **kwargs) + diff --git a/tests/test_fingerprint.py b/tests/test_fingerprint.py index 6d9661f..ab97954 100644 --- a/tests/test_fingerprint.py +++ b/tests/test_fingerprint.py @@ -6,6 +6,8 @@ _return_first_element) from prolif.interactions import Interaction from prolif.residue import ResidueId +from prolif.datafiles import datapath +from prolif.molecule import sdf_supplier from .test_base import protein_mol, ligand_mol, u, ligand_ag, protein_ag @@ -104,6 +106,12 @@ def test_run_return_atoms(self, fp_class): ifp.pop("Frame") atom_pair = list(ifp.values())[0] assert isinstance(atom_pair, list) + + def test_run_from_iterable(self, fp): + path = str(datapath / "vina" / "vina_output.sdf") + lig_suppl = list(sdf_supplier(path)) + fp.run_from_iterable(lig_suppl[:2], protein_mol, progress=False) + assert len(fp.ifp) == 2 def test_to_df(self, fp, fp_class): with pytest.raises(AttributeError, match="use the run method"): diff --git a/tests/test_molecule.py b/tests/test_molecule.py index acc01f4..1a7795d 100644 --- a/tests/test_molecule.py +++ b/tests/test_molecule.py @@ -1,6 +1,11 @@ import pytest -from prolif.molecule import Molecule +from rdkit import Chem +from prolif.molecule import (Molecule, + pdbqt_supplier, + mol2_supplier, + sdf_supplier) from prolif.residue import ResidueId +from prolif.datafiles import datapath from .test_base import TestBaseRDKitMol, rdkit_mol, ligand_rdkit, u @@ -19,6 +24,17 @@ def test_from_mda(self): assert rdkit_mol[0].resid == mda_mol[0].resid assert (rdkit_mol.HasSubstructMatch(mda_mol) and mda_mol.HasSubstructMatch(rdkit_mol)) + + def test_from_rdkit(self): + rdkit_mol = Molecule(ligand_rdkit) + newmol = Molecule.from_rdkit(ligand_rdkit) + assert rdkit_mol[0].resid == newmol[0].resid + mol = Chem.MolFromSmiles("CCO") + newmol = Molecule.from_rdkit(mol) + assert newmol[0].resid == ResidueId("UNL", 1) + newmol = Molecule.from_rdkit(mol, "FOO", 42, "A") + assert newmol[0].resid == ResidueId("FOO", 42, "A") + @pytest.mark.parametrize("key", [ 0, @@ -36,3 +52,38 @@ def test_iter(self, mol): def test_n_residues(self, mol): assert mol.n_residues == mol.residues.n_residues + + +class TestSupplier: + def test_pdbqt(self): + path = datapath / "vina" + pdbqts = sorted(path.glob("*.pdbqt")) + template = Chem.MolFromSmiles("C[NH+]1CC(C(=O)NC2(C)OC3(O)C4CCCN4C(=O)" + "C(Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc" + "(c34)CC21") + suppl = pdbqt_supplier(pdbqts, template) + mols = list(suppl) + assert isinstance(mols[0], Molecule) + assert len(mols) == len(pdbqts) + + def test_sdf(self): + path = str(datapath / "vina" / "vina_output.sdf") + suppl = sdf_supplier(path) + mols = list(suppl) + assert isinstance(mols[0], Molecule) + assert len(mols) == 9 + mi = mols[0].GetAtomWithIdx(0).GetMonomerInfo() + assert all([mi.GetResidueName() == "UNL", + mi.GetResidueNumber() == 1, + mi.GetChainId() == ""]) + + def test_mol2(self): + path = str(datapath / "vina" / "vina_output.mol2") + suppl = mol2_supplier(path) + mols = list(suppl) + assert isinstance(mols[0], Molecule) + assert len(mols) == 9 + mi = mols[0].GetAtomWithIdx(0).GetMonomerInfo() + assert all([mi.GetResidueName() == "UNL", + mi.GetResidueNumber() == 1, + mi.GetChainId() == ""])