write main mcss clustering loop

examples/chemical_series_clustering.ipynb

@@ -66,7 +66,7 @@
    "outputs": [],
    "source": [
     "from rdkit import Chem\n",
-    "mols = Chem.SDMolSupplier(mypath)"
+    "mols = Chem.SDMolSupplier(str(mypath))"
    ]
   },
   {
@@ -93,7 +93,7 @@
    "metadata": {},
    "outputs": [],
    "source": [
-    "# define the grid to show the scafffolds\n",
+    "# define the grid to show the scaffolds\n",
     "grid = mols2grid.display(mols)"
    ]
   },
@@ -106,12 +106,206 @@
     "grid"
    ]
   },
+  {
+   "cell_type": "markdown",
+   "source": [
+    "# MCSS-based Clustering"
+   ],
+   "metadata": {
+    "collapsed": false
+   }
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "from harbor.clustering.hierarchical import ClusterResults, ClusterCenter, HeirarchicalClustering\n",
+    "from openeye import oechem"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "mol: Chem.Mol = mols[0]\n",
+    "mol.GetPropsAsDict()"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "oemols = []\n",
+    "mol_ids = []\n",
+    "for rdkit_mol in mols[:20]:\n",
+    "    smiles = Chem.MolToSmiles(rdkit_mol)\n",
+    "    properties = rdkit_mol.GetPropsAsDict()\n",
+    "    mol_ids.append(properties[\"Compound_ID\"])\n",
+    "    mol = oechem.OEMol()\n",
+    "    oechem.OESmilesToMol(mol, smiles)\n",
+    "    oemols.append(mol)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "from harbor.clustering import hierarchical as h\n",
+    "from importlib import reload\n",
+    "reload(h)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "clusterer = h.HeirarchicalClustering(molecules=oemols, mol_ids=mol_ids)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "clusters = clusterer.cluster(max_iterations=10)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "len(clusters)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "def get_descendents(cluster):\n",
+    "    descendents = []\n",
+    "    for child in cluster.children:\n",
+    "        if isinstance(child, str):\n",
+    "            descendents.append(cluster)\n",
+    "        else:\n",
+    "            descendents.extend(get_descendents(child))\n",
+    "    return descendents"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "from harbor.plotting import ligands as l\n",
+    "reload(l)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "ids_found = []\n",
+    "for cluster_id, cluster in clusters.items():\n",
+    "    print(f\"Cluster {cluster_id}\")\n",
+    "    descendents = get_descendents(cluster)\n",
+    "    print(f\"Children: {len(descendents)}\")\n",
+    "    l.plot_ligands_with_mcs(filename=f\"cluster_{cluster_id}.png\", mols=[desc.repr for desc in descendents], mcs_mol=cluster.repr)\n",
+    "    ids_found.extend([desc.children[0] for desc in descendents])"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "set(ids_found)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "set(mol_ids) - set(ids_found)"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "def get_row_col(i, max_cols, zero_indexed=True):\n",
+    "    row = i // max_cols + (0 if zero_indexed else 1)\n",
+    "    col = i % max_cols + (0 if zero_indexed else 1)\n",
+    "    return row, col"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
+  {
+   "cell_type": "code",
+   "outputs": [],
+   "source": [
+    "for i in range(6):\n",
+    "    print(get_row_col(i, 4, zero_indexed=False))"
+   ],
+   "metadata": {
+    "collapsed": false
+   },
+   "execution_count": null
+  },
   {
    "cell_type": "code",
-   "execution_count": null,
-   "metadata": {},
    "outputs": [],
-   "source": []
+   "source": [],
+   "metadata": {
+    "collapsed": false
+   }
   }
  ],
  "metadata": {