--- name: pharmaclaw-cheminformatics description: Advanced cheminformatics agent for 3D molecular analysis, pharmacophore mapping, format conversion, RECAP fragmentation, and stereoisomer enumeration. The "senior cheminformatician" upgrade to Chemistry Query. Use for 3D conformer generation/ensembles (ETKDG + MMFF/UFF), pharmacophore feature extraction and fingerprints, molecular format conversion (SMILES/SDF/MOL/InChI/PDB/XYZ), RECAP retrosynthetic fragmentation for library design, stereoisomer enumeration (R/S, E/Z), and cheminformatics profiling. Chains from chemistry-query (receives SMILES) and feeds into pharmacology, catalyst-design, ip-expansion. Triggers on conformer, 3D structure, pharmacophore, SDF, MOL file, format conversion, RECAP, fragmentation, stereoisomer, chirality, enantiomer, cheminformatics, library design, building blocks, docking prep. --- # Cheminformatics Agent v1.0.0 ## Overview Advanced cheminformatics toolkit for 3D molecular analysis and drug development workflows. Extends Chemistry Query (which handles 2D lookup/properties/visualization) with predictive and structural capabilities that require 3D reasoning. **Chemistry Query** = "What is this molecule?" (2D, lookup, descriptors) **Cheminformatics** = "What can this molecule become?" (3D, conformers, pharmacophores, fragments, stereoisomers) ## Scripts ### `scripts/conformer_gen.py` 3D conformer ensemble generation using ETKDG with MMFF/UFF optimization. ``` --smiles --action [--num_confs N] [--optimize mmff|uff|none] [--energy_window F] [--prune_rms F] [--output file.sdf] ``` | Action | Description | |--------|-------------| | generate | Generate N conformers with energies and RMSD matrix | | ensemble | Same as generate + write SDF file | | best | Find lowest-energy conformer with 3D coordinates | ```bash python scripts/conformer_gen.py --smiles "CC(=O)Oc1ccccc1C(=O)O" --action generate --num_confs 20 python scripts/conformer_gen.py --smiles "CCO" --action best --output best.sdf python scripts/conformer_gen.py --smiles "c1ccccc1" --action ensemble --num_confs 50 --output benzene_confs.sdf ``` Output includes: conformer energies (kcal/mol), relative energies, convergence status, RMSD matrix (top 20), SDF file. ### `scripts/format_converter.py` Convert between molecular file formats. ``` --smiles | --input --to [--output file] [--batch] [--name label] ``` Supported formats: `smiles`, `sdf`, `mol`, `inchi`, `inchikey`, `pdb`, `xyz` ```bash python scripts/format_converter.py --smiles "CCO" --to sdf --output ethanol.sdf python scripts/format_converter.py --smiles "CCO" --to inchi python scripts/format_converter.py --input mols.sdf --to smiles --batch python scripts/format_converter.py --smiles "CCO" --to pdb --output ethanol.pdb ``` Batch mode reads multi-molecule SDF files. All 3D formats auto-generate and optimize conformers. ### `scripts/pharmacophore.py` Pharmacophore feature extraction, fingerprints, and comparison. ``` --smiles --action [--target_smiles "smi1,smi2"] [--output file.png] ``` | Action | Description | |--------|-------------| | features | Extract 3D pharmacophoric features (HBD, HBA, aromatic, hydrophobic, ionizable) with coordinates | | fingerprint | Generate Gobbi 2D pharmacophore fingerprint | | compare | Pairwise pharmacophore similarity (Tanimoto) across multiple molecules | | map | Generate color-coded pharmacophore PNG (green=donor, red=acceptor, yellow=aromatic, blue=hydrophobic) | ```bash python scripts/pharmacophore.py --smiles "CC(=O)Oc1ccccc1C(=O)O" --action features python scripts/pharmacophore.py --smiles "CC(=O)Oc1ccccc1C(=O)O" --action map --output pharm.png python scripts/pharmacophore.py --target_smiles "CCO,CC(=O)O,c1ccccc1" --action compare ``` ### `scripts/recap_fragment.py` RECAP (Retrosynthetic Combinatorial Analysis Procedure) fragmentation at synthetically accessible bonds (amide, ester, amine, urea, ether, olefin, sulfonamide, etc.). ``` --smiles --action [--target_smiles "smi1,smi2"] [--max_depth N] ``` | Action | Description | |--------|-------------| | fragment | All RECAP fragments with metadata | | leaves | Terminal building blocks only (for library design) | | tree | Hierarchical decomposition tree | | common_fragments | Shared fragments across multiple molecules (common scaffolds) | ```bash python scripts/recap_fragment.py --smiles "CC(=O)Nc1ccc(O)cc1" --action fragment python scripts/recap_fragment.py --smiles "CC(=O)Nc1ccc(O)cc1" --action leaves python scripts/recap_fragment.py --target_smiles "CC(=O)Nc1ccc(O)cc1,CC(=O)Nc1ccccc1" --action common_fragments ``` Use case: Leaf fragments → building blocks for combinatorial library enumeration. Common fragments across a compound series → shared pharmacophoric scaffolds. ### `scripts/stereoisomers.py` Stereoisomer enumeration and analysis (chiral centers R/S, double bond E/Z). ``` --smiles --action [--max_isomers N] [--only_unassigned] ``` | Action | Description | |--------|-------------| | enumerate | Generate all stereoisomers with configurations | | analyze | Count chiral centers and stereo bonds without enumerating | | compare | Compare properties across all stereoisomers (drug dev relevance) | ```bash python scripts/stereoisomers.py --smiles "C(F)(Cl)Br" --action enumerate python scripts/stereoisomers.py --smiles "CC=CC" --action analyze python scripts/stereoisomers.py --smiles "OC(F)(Cl)Br" --action compare ``` Drug relevance: FDA requires characterization of each stereoisomer for chiral drug candidates. Flags meso forms and provides R/S assignments. ### `scripts/chain_entry.py` Standard agent chain interface. Runs all 5 modules on a SMILES input. ```bash python scripts/chain_entry.py --input-json '{"smiles": "CC(=O)Nc1ccc(O)cc1", "context": "user"}' python scripts/chain_entry.py --input-json '{"smiles": "CCO", "actions": ["conformers", "pharmacophore"]}' ``` Input JSON fields: - `smiles` (required): Input SMILES - `context`: Chain context string - `actions`: Array to run subset — `["conformers", "pharmacophore", "recap", "stereoisomers", "formats"]` - `output_dir`: Directory for SDF/PNG output files Output schema: ```json { "agent": "cheminformatics", "version": "1.0.0", "smiles": "", "status": "success|error", "report": { "conformers": {...}, "pharmacophore": {...}, "recap": {...}, "stereoisomers": {...}, "formats": {...} }, "risks": [], "warnings": [], "viz": ["path/to/file.sdf", "path/to/pharmacophore_map.png"], "recommend_next": ["pharmacology", "catalyst-design", "ip-expansion"], "confidence": 0.9, "timestamp": "ISO8601" } ``` ## Chaining | From | To | What passes | |------|----|-------------| | Chemistry Query → | **Cheminformatics** | SMILES + basic properties | | **Cheminformatics** → | Pharmacology | SMILES + pharmacophore profile for ADME context | | **Cheminformatics** → | Catalyst Design | 3D conformer data for catalyst selection | | **Cheminformatics** → | IP Expansion | Stereoisomers as patentable variants | | **Cheminformatics** → | Toxicology | Fragment analysis for structural alerts | ## Dependencies - Python ≥ 3.10 - rdkit-pypi - Pillow (for pharmacophore map PNG) - numpy

Pharmaclaw Cheminformatics

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