DebiChem Cheminformatics packages

The CDK is a library of Java classes used in computational and information chemistry and in bioinformatics. It includes renderers, file IO, SMILES generation/parsing, maximal common substructure algorithms, fingerprinting and much, much more.

ChemicalTagger parser is a medium-depth, phrase-based semantic NLP tool for the language of chemical experiments. Tagging is based on a modular architecture and uses a combination of OSCAR, domain-specific regex and English taggers to identify parts-of-speech. The ANTLR grammar is used to structure this into tree-based phrases.

The International Chemical Identifier (InChI) is an Open Source chemical structure representation algorithm.

InChIs are text strings comprising different layers and sublayers of information separated by slashes (/). Each InChI strings starts with the InChI version number followed by the main layer. This main layer contains sublayers for chemical formula, atom connections and hydrogen atoms. Depending on the structure of the molecule the main layer may be followed by additional layers e. g. for charge, stereochemical and/or isotop information.

This package contains the executable, inchi_main.

JNI-InChI provides JNI (Java Native Interface) wrappers for the InChI (International Chemical Identifier) C library distributed by IUPAC. All of the features from the InChI libarary are supported:

• Standard and Non-Standard InChI generation from structures with 3D, 2D, or no coordinates
• Structure generation (without coordinates) from InChI
• InChIKey generation
• Check InChI / InChIKey
• InChI-to-InChI conversion
• AuxInfo to InChI input
• Access to the full range of options supported by InChI
• Full support for InChI's handling of stereochemistry

OpenChemLib is Java based framework providing cheminformatics core functionality and user interface components. Its main focus is on organics chemistry and small molecules. It is built around a StereoMolecule class, which represents a molecule using atom and bond tables, provides atom neighbours, ring and aromaticity information, and supports MDL's concept of enhanced stereo representation. Additional classes provide, 2D-depiction, descriptor calculation, molecular similarity and substructure search, reaction search, property prediction, conformer generation, support for molfile and SMILES formats, energy minimization, ligand-protein interactions, and more. OpenChemLib's idcode represents molecules, fragments or reactions as canonical, very compact string that includes stereo and query features.

Different to other cheminformatics frameworks, OpenChemLib also provides user interface components that allow one to easily embed chemical functionality into Java applications, e.g. to display or edit chemical structures or reactions.

OPSIN (Open Parser for Systematic IUPAC Nomenclature) converts IUPAC compound names to semantic chemical information and outputs a structure either as CML (Chemical Markup Language), SMILES, or InChI.

This package contains the Java library.

OSCAR (Open Source Chemistry Analysis Routines) is an open source extensible system for the automated annotation of chemistry in scientific articles. It can be used to identify chemical names, reaction names, ontology terms, enzymes and chemical prefixes and adjectives, and chemical data such as state, yield, IR, NMR and mass spectra and elemental analyses. In addition, where possible, any chemical names detected will be annotated with structures derived either by lookup, or name-to-structure parsing using OPSIN or with identifiers from the ChEBI (Chemical Entities of Biological Interest) ontology.

Open Babel is a chemical toolbox designed to speak the many languages of chemical data. It allows one to search, convert, analyze, or store data from molecular modeling, chemistry, solid-state materials, biochemistry, or related areas. Features include:

• Hydrogen addition and deletion
• Support for Molecular Mechanics
• Support for SMARTS molecular matching syntax
• Automatic feature perception (rings, bonds, hybridization, aromaticity)
• Flexible atom typer and perception of multiple bonds from atomic coordinates
• Gasteiger-Marsili partial charge calculation

File formats Open Babel supports include PDB, XYZ, CIF, CML, SMILES, MDL Molfile, ChemDraw, Gaussian, GAMESS, MOPAC and MPQC.

This package includes the following utilities:

• obabel: Convert between various chemical file formats
• obenergy: Calculate the energy for a molecule
• obminimize: Optimize the geometry, minimize the energy for a molecule
• obgrep: Molecular search program using SMARTS pattern
• obgen: Generate 3D coordinates for a molecule
• obprop: Print standard molecular properties
• obfit: Superimpose two molecules based on a pattern
• obrotamer: Generate conformer/rotamer coordinates
• obconformer: Generate low-energy conformers
• obchiral: Print molecular chirality information
• obrotate: Rotate dihedral angle of molecules in batch mode
• obprobe: Create electrostatic probe grid

OSRA is a utility designed to convert graphical representations of chemical structures, as they appear in journal articles, patent documents, textbooks, trade magazines etc., into SMILES (Simplified Molecular Input Line Entry Specification) - a computer recognizable molecular structure format. OSRA can read a document in any of the over 90 graphical formats parseable by ImageMagick - including GIF, JPEG, PNG, TIFF, PDF, PS etc., and generate the SMILES representation of the molecular structure images encountered within that document.

Indigo is a C++ based organic chemistry and cheminformatics software environment. Features Include:

• Molecule and reaction rendering including SVG support
• Automatic layout for SMILES-represented molecules and reactions
• Canonical (isomeric) SMILES computation
• Exact matching, substructure matching, SMARTS matching
• Matching of tautomers and resonance structures
• Molecule fingerprinting, molecule similarity computation
• Fast enumeration of SSSR rings, subtrees, and edge sugraphs
• Molecular weight, molecular formula computation
• R-Group deconvolution and scaffold detection
• Computation of the exact maximum common substructure for an arbitrary amount of input structures
• Combinatorial chemistry
• Plugin support in the API

File formats Indigo support include MDL Mol, SDF, RDF, CML, SMILES and SMARTS.

This package contains the Python modules.

Open Babel is a chemical toolbox designed to speak the many languages of chemical data. It allows one to search, convert, analyze, or store data from molecular modeling, chemistry, solid-state materials, biochemistry, or related areas. Features include:

• Hydrogen addition and deletion
• Support for Molecular Mechanics
• Support for SMARTS molecular matching syntax
• Automatic feature perception (rings, bonds, hybridization, aromaticity)
• Flexible atom typer and perception of multiple bonds from atomic coordinates
• Gasteiger-Marsili partial charge calculation

File formats Open Babel supports include PDB, XYZ, CIF, CML, SMILES, MDL Molfile, ChemDraw, Gaussian, GAMESS, MOPAC and MPQC.

This package contains the Python binding.

RDKit is a Python/C++ based cheminformatics and machine-learning software environment. Features Include:

• Chemical reaction handling and transforms
• Substructure searching with SMARTS
• Canonical SMILES
• Molecule-molecule alignment
• Large number of molecular descriptors, including topological, compositional, EState, SlogP/SMR, VSA and Feature-map vectors
• Fragmentation using RECAP rules
• 2D coordinate generation and depiction, including constrained depiction
• 3D coordinate generation using geometry embedding
• UFF and MMFF94 forcefields
• Chirality support, including calculation of (R/S) stereochemistry codes
• 2D pharmacophore searching
• Fingerprinting, including Daylight-like, atom pairs, topological torsions, Morgan algorithm and MACCS keys
• Calculation of shape similarity
• Multi-molecule maximum common substructure
• Machine-learning via clustering and information theory algorithms
• Gasteiger-Marsili partial charge calculation

File formats RDKit supports include MDL Mol, PDB, SDF, TDT, SMILES and RDKit binary format.

Package provides command line tools to work with Simplified Molecular-Input Line-Entry System (SMILES) descriptors. Package contains command line interface scripts for Chemistry Development Kit (CDK), as well as a syntax checker for SMILES.