@synsci/cli-darwin-x64-baseline 1.1.76 → 1.1.78

package/bin/skills/molfeat/references/available_featurizers.md

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+# Available Featurizers in Molfeat
+
+This document provides a comprehensive catalog of all featurizers available in molfeat, organized by category.
+
+## Transformer-Based Language Models
+
+Pre-trained transformer models for molecular embeddings using SMILES/SELFIES representations.
+
+### RoBERTa-style Models
+- **Roberta-Zinc480M-102M** - RoBERTa masked language model trained on ~480M SMILES strings from ZINC database
+- **ChemBERTa-77M-MLM** - Masked language model based on RoBERTa trained on 77M PubChem compounds
+- **ChemBERTa-77M-MTR** - Multitask regression version trained on PubChem compounds
+
+### GPT-style Autoregressive Models
+- **GPT2-Zinc480M-87M** - GPT-2 autoregressive language model trained on ~480M SMILES from ZINC
+- **ChemGPT-1.2B** - Large transformer (1.2B parameters) pretrained on PubChem10M
+- **ChemGPT-19M** - Medium transformer (19M parameters) pretrained on PubChem10M
+- **ChemGPT-4.7M** - Small transformer (4.7M parameters) pretrained on PubChem10M
+
+### Specialized Transformer Models
+- **MolT5** - Self-supervised framework for molecule captioning and text-based generation
+
+## Graph Neural Networks (GNNs)
+
+Pre-trained graph neural network models operating on molecular graph structures.
+
+### GIN (Graph Isomorphism Network) Variants
+All pre-trained on ChEMBL molecules with different objectives:
+- **gin-supervised-masking** - Supervised with node masking objective
+- **gin-supervised-infomax** - Supervised with graph-level mutual information maximization
+- **gin-supervised-edgepred** - Supervised with edge prediction objective
+- **gin-supervised-contextpred** - Supervised with context prediction objective
+
+### Other Graph-Based Models
+- **JTVAE_zinc_no_kl** - Junction-tree VAE for molecule generation (trained on ZINC)
+- **Graphormer-pcqm4mv2** - Graph transformer pretrained on PCQM4Mv2 quantum chemistry dataset for HOMO-LUMO gap prediction
+
+## Molecular Descriptors
+
+Calculators for physico-chemical properties and molecular characteristics.
+
+### 2D Descriptors
+- **desc2D** / **rdkit2D** - 200+ RDKit 2D molecular descriptors including:
+  - Molecular weight, logP, TPSA
+  - H-bond donors/acceptors
+  - Rotatable bonds
+  - Ring counts and aromaticity
+  - Molecular complexity metrics
+
+### 3D Descriptors
+- **desc3D** / **rdkit3D** - RDKit 3D molecular descriptors (requires conformer generation)
+  - Inertial moments
+  - PMI (Principal Moments of Inertia) ratios
+  - Asphericity, eccentricity
+  - Radius of gyration
+
+### Comprehensive Descriptor Sets
+- **mordred** - Over 1800 molecular descriptors covering:
+  - Constitutional descriptors
+  - Topological indices
+  - Connectivity indices
+  - Information content
+  - 2D/3D autocorrelations
+  - WHIM descriptors
+  - GETAWAY descriptors
+  - And many more
+
+### Electrotopological Descriptors
+- **estate** - Electrotopological state (E-State) indices encoding:
+  - Atomic environment information
+  - Electronic and topological properties
+  - Heteroatom contributions
+
+## Molecular Fingerprints
+
+Binary or count-based fixed-length vectors representing molecular substructures.
+
+### Circular Fingerprints (ECFP-style)
+- **ecfp** / **ecfp:2** / **ecfp:4** / **ecfp:6** - Extended-connectivity fingerprints
+  - Radius variants (2, 4, 6 correspond to diameter)
+  - Default: radius=3, 2048 bits
+  - Most popular for similarity searching
+- **ecfp-count** - Count version of ECFP (non-binary)
+- **fcfp** / **fcfp-count** - Functional-class circular fingerprints
+  - Similar to ECFP but uses functional groups
+  - Better for pharmacophore-based similarity
+
+### Path-Based Fingerprints
+- **rdkit** - RDKit topological fingerprints based on linear paths
+- **pattern** - Pattern fingerprints (similar to MACCS but automated)
+- **layered** - Layered fingerprints with multiple substructure layers
+
+### Key-Based Fingerprints
+- **maccs** - MACCS keys (166-bit structural keys)
+  - Fixed set of predefined substructures
+  - Good for scaffold hopping
+  - Fast computation
+- **avalon** - Avalon fingerprints
+  - Similar to MACCS but more features
+  - Optimized for similarity searching
+
+### Atom-Pair Fingerprints
+- **atompair** - Atom pair fingerprints
+  - Encodes pairs of atoms and distance between them
+  - Good for 3D similarity
+- **atompair-count** - Count version of atom pairs
+
+### Topological Torsion Fingerprints
+- **topological** - Topological torsion fingerprints
+  - Encodes sequences of 4 connected atoms
+  - Captures local topology
+- **topological-count** - Count version of topological torsions
+
+### MinHashed Fingerprints
+- **map4** - MinHashed Atom-Pair fingerprint up to 4 bonds
+  - Combines atom-pair and ECFP concepts
+  - Default: 1024 dimensions
+  - Fast and efficient for large datasets
+- **secfp** - SMILES Extended Connectivity Fingerprint
+  - Operates directly on SMILES strings
+  - Captures both substructure and atom-pair information
+
+### Extended Reduced Graph
+- **erg** - Extended Reduced Graph
+  - Uses pharmacophoric points instead of atoms
+  - Reduces graph complexity while preserving key features
+
+## Pharmacophore Descriptors
+
+Features based on pharmacologically relevant functional groups and their spatial relationships.
+
+### CATS (Chemically Advanced Template Search)
+- **cats2D** - 2D CATS descriptors
+  - Pharmacophore point pair distributions
+  - Distance based on shortest path
+  - 21 descriptors by default
+- **cats3D** - 3D CATS descriptors
+  - Euclidean distance based
+  - Requires conformer generation
+- **cats2D_pharm** / **cats3D_pharm** - Pharmacophore variants
+
+### Gobbi Pharmacophores
+- **gobbi2D** - 2D pharmacophore fingerprints
+  - 8 pharmacophore feature types:
+    - Hydrophobic
+    - Aromatic
+    - H-bond acceptor
+    - H-bond donor
+    - Positive ionizable
+    - Negative ionizable
+    - Lumped hydrophobe
+  - Good for virtual screening
+
+### Pmapper Pharmacophores
+- **pmapper2D** - 2D pharmacophore signatures
+- **pmapper3D** - 3D pharmacophore signatures
+  - High-dimensional pharmacophore descriptors
+  - Useful for QSAR and similarity searching
+
+## Shape Descriptors
+
+Descriptors capturing 3D molecular shape and electrostatic properties.
+
+### USR (Ultrafast Shape Recognition)
+- **usr** - Basic USR descriptors
+  - 12 dimensions encoding shape distribution
+  - Extremely fast computation
+- **usrcat** - USR with pharmacophoric constraints
+  - 60 dimensions (12 per feature type)
+  - Combines shape and pharmacophore information
+
+### Electrostatic Shape
+- **electroshape** - ElectroShape descriptors
+  - Combines molecular shape, chirality, and electrostatics
+  - Useful for protein-ligand docking predictions
+
+## Scaffold-Based Descriptors
+
+Descriptors based on molecular scaffolds and core structures.
+
+### Scaffold Keys
+- **scaffoldkeys** - Scaffold key calculator
+  - 40+ scaffold-based properties
+  - Bioisosteric scaffold representation
+  - Captures core structural features
+
+## Graph Featurizers for GNN Input
+
+Atom and bond-level features for constructing graph representations for Graph Neural Networks.
+
+### Atom-Level Features
+- **atom-onehot** - One-hot encoded atom features
+- **atom-default** - Default atom featurization including:
+  - Atomic number
+  - Degree, formal charge
+  - Hybridization
+  - Aromaticity
+  - Number of hydrogen atoms
+
+### Bond-Level Features
+- **bond-onehot** - One-hot encoded bond features
+- **bond-default** - Default bond featurization including:
+  - Bond type (single, double, triple, aromatic)
+  - Conjugation
+  - Ring membership
+  - Stereochemistry
+
+## Integrated Pretrained Model Collections
+
+Molfeat integrates models from various sources:
+
+### HuggingFace Models
+Access to transformer models through HuggingFace hub:
+- ChemBERTa variants
+- ChemGPT variants
+- MolT5
+- Custom uploaded models
+
+### DGL-LifeSci Models
+Pre-trained GNN models from DGL-Life:
+- GIN variants with different pre-training tasks
+- AttentiveFP models
+- MPNN models
+
+### FCD (Fréchet ChemNet Distance)
+- **fcd** - Pre-trained CNN for molecular generation evaluation
+
+### Graphormer Models
+- Graph transformers from Microsoft Research
+- Pre-trained on quantum chemistry datasets
+
+## Usage Notes
+
+### Choosing a Featurizer
+
+**For traditional ML (Random Forest, SVM, etc.):**
+- Start with **ecfp** or **maccs** fingerprints
+- Try **desc2D** for interpretable models
+- Use **FeatConcat** to combine multiple fingerprints
+
+**For deep learning:**
+- Use **ChemBERTa** or **ChemGPT** for transformer embeddings
+- Use **gin-supervised-*** for graph neural network embeddings
+- Consider **Graphormer** for quantum property predictions
+
+**For similarity searching:**
+- **ecfp** - General purpose, most popular
+- **maccs** - Fast, good for scaffold hopping
+- **map4** - Efficient for large-scale searches
+- **usr** / **usrcat** - 3D shape similarity
+
+**For pharmacophore-based approaches:**
+- **fcfp** - Functional group based
+- **cats2D/3D** - Pharmacophore pair distributions
+- **gobbi2D** - Explicit pharmacophore features
+
+**For interpretability:**
+- **desc2D** / **mordred** - Named descriptors
+- **maccs** - Interpretable substructure keys
+- **scaffoldkeys** - Scaffold-based features
+
+### Model Dependencies
+
+Some featurizers require optional dependencies:
+
+- **DGL models** (gin-*, jtvae): `pip install "molfeat[dgl]"`
+- **Graphormer**: `pip install "molfeat[graphormer]"`
+- **Transformers** (ChemBERTa, ChemGPT, MolT5): `pip install "molfeat[transformer]"`
+- **FCD**: `pip install "molfeat[fcd]"`
+- **MAP4**: `pip install "molfeat[map4]"`
+- **All dependencies**: `pip install "molfeat[all]"`
+
+### Accessing All Available Models
+
+```python
+from molfeat.store.modelstore import ModelStore
+
+store = ModelStore()
+all_models = store.available_models
+
+# Print all available featurizers
+for model in all_models:
+    print(f"{model.name}: {model.description}")
+
+# Search for specific types
+transformers = [m for m in all_models if "transformer" in m.tags]
+gnn_models = [m for m in all_models if "gnn" in m.tags]
+fingerprints = [m for m in all_models if "fingerprint" in m.tags]
+```
+
+## Performance Characteristics
+
+### Computational Speed (relative)
+**Fastest:**
+- maccs
+- ecfp
+- rdkit fingerprints
+- usr
+
+**Medium:**
+- desc2D
+- cats2D
+- Most fingerprints
+
+**Slower:**
+- mordred (1800+ descriptors)
+- desc3D (requires conformer generation)
+- 3D descriptors in general
+
+**Slowest (first run):**
+- Pretrained models (ChemBERTa, ChemGPT, GIN)
+- Note: Subsequent runs benefit from caching
+
+### Dimensionality
+
+**Low (< 200 dims):**
+- maccs (167)
+- usr (12)
+- usrcat (60)
+
+**Medium (200-2000 dims):**
+- desc2D (~200)
+- ecfp (2048 default, configurable)
+- map4 (1024 default)
+
+**High (> 2000 dims):**
+- mordred (1800+)
+- Concatenated fingerprints
+- Some transformer embeddings
+
+**Variable:**
+- Transformer models (typically 768-1024)
+- GNN models (depends on architecture)