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Chython [ˈkʌɪθ(ə)n]

PyPI version Python versions License: LGPLv3 Documentation Coverage of the Python layers

Library for processing molecules and reactions in a Python way.

Features

File formats

  • Read and write MDL RDF/RXN and SDF/MOL (V2000 and V3000, including atom parity and enhanced stereo), Marvin MRV, CML, SMILES, and InChI with InChIKey (InChI Trust library)
  • Read SMARTS and SMIRKS, Tripos MOL2, PDBx/mmCIF, legacy PDB, XYZ, and IUPAC names through OPSIN
  • Compact binary (de)serialization — pach for a wire record, mol.to_bytes() for the arena buffer — and full pickle support
  • A coordinate format hands back a record of atoms and coordinates rather than a molecule, because it states no bond order: build_molecule() places the atoms, perceive_bonds() reads the connectivity out of a geometry, saturate() raises the orders, and all three are calls the caller makes

Input is unreliable by default

A reader stores and logs what a file says — an illegal valence, a nonsense charge, an underivable hydrogen count — and never rejects a record for being chemically wrong. Repair is a pipeline you run afterwards: kekule(), standardize(), fix_resonance(), thiele().

Toolkit interoperability

Conversions build the target structure directly from the graph, so atom order matches atoms() and stereo is carried over without needing a 2D layout. Each toolkit has one callable in chython.interop that dispatches on its argument, and the export direction is also a container method.

Toolkit API Requires
RDKit mol.to_rdkit(), rxn.to_rdkit(), chython.interop.rdkit() both ways extra rdkit
Open Babel mol.to_openbabel() extra extra-clean2d
Indigo mol.to_indigo() extra extra-clean2d
CDK mol.to_cdk() extra extra-clean2d + cdk.jar (CDK_PATH)
CDPKit mol.to_cdpkit(), and 3D conformers (conformer_engine = 'cdpkit') extra extra-clean3d

RDKit is the only one of the five with a reaction form.

Allene stereo is not portable through any of these toolkits. Indigo additionally omits cis-trans, which it derives from 2D coordinates.

IUPAC names, both directions

from chython import iupac

mol = iupac('ethanol')   # name -> structure, via OPSIN
mol.iupac                # 'ethanol' -- structure -> name, via openclatura

iupac() needs JPype and opsin.jar (OPSIN_PATH); the .iupac property needs the iupac extra (Python >= 3.11) and returns None when the structure cannot be named.

Molecules

  • Atoms and bonds in one contiguous buffer, addressed by an id that survives editing; edits go through an explicit session (with mol.edit() as e:) and derived data is recomputed on seal
  • Standardize, canonicalize, kekulize/aromatize, repair resonance forms, neutralize, put a mobile hydrogen and charge where the canonical order says, check valences
  • Split and decompose salts, expand contracted groups, derive implicit hydrogen counts
  • Many 3D models per molecule in one conformer store
  • Tetrahedral, cis-trans, allene, atropisomer and helical stereo, with CIP labels
  • Descriptors: TPSA, Crippen logP and MR, hydrogen-bond donors and acceptors, rotatable bonds, ring counts, Bertz CT, Randić and Zagreb indices
  • The 166 MACCS structural keys, one-based, and QED with its three published weight sets — both state what they transcribe and neither claims parity with another implementation's bits or score
  • Morgan and linear fingerprints with Tanimoto similarity, as hash sets, folded bit vectors or count vectors, and the graph matrices and distance-derived descriptors — extra ml
  • A molecule or a mapped reaction as int32 arrays for a model: mol.state_view(), rxn.transition_view() — extra ml

Search

  • Subgraph isomorphism
  • SMARTS parser with chython-specific query semantics, including component grouping for intramolecular patterns

Reactions

  • Template application from SMIRKS: mol.react(template), or mol @ other for a two-component join
  • Reaction enumeration over the shipped reaction corpus
  • Functional and protective group detection and deprotection, with the whole corpus in the docs
  • Sticky fragment / linker enumeration for combinatorial reassembly
  • Atom-to-atom mapping reconstruction against a template corpus: rxn.reconstruct_mapping()
  • Reaction-level standardization: each molecule pass once per molecule, plus the passes a loop cannot do

Depiction

  • 2D coordinate generation, default SmilesDrawer, switchable to RDKit/CDK/Open Babel/Indigo (clean2d_engine)
  • SVG and SVGZ output with Jupyter support, and scalar data overlaid on the same scene
  • 3D: a stored conformer as an X3DOM document (mol.depict3d()) or a notebook widget (mol.view3d())
  • 3D conformer generation with RDKit or CDPKit (conformer_engine)

Full documentation can be found here.

Install

Only Python 3.10+.

pip install chython

The default 2D layout backend needs no extra: its JS engine (QuickJS) is a required dependency and costs under 2.5 MB.

A plain install has no numpy, and that is deliberate — the base install is about 7.5 MB of runtime files, small enough for a serverless bundle. Reading and writing every format, standardize(), kekule(), thiele(), canonicalize(), stereo, substructure matching, template application and depiction all work without it. What needs chython[ml] is the surface that answers a numpy array: the fingerprints, atom_invariants, adjacency_matrix, distance_matrix, the distance-derived graph descriptors, pharmacophore_invariants, maccs_keys()/maccs_bit_set() and the ML views. Each of those raises an ImportError naming the extra when you call it, so nothing fails at import time.

Optional extras, combinable (chython[rdkit,iupac]):

Extra Enables
ml numpy, and with it fingerprints, atom invariants, the graph matrices, the descriptors built on them and the ML views
rdkit RDKit conversion both ways, RDKit 2D layout and 3D conformers
iupac molecule.iupac name generation (Python >= 3.11)
extra-clean2d CDK, Open Babel and Indigo backends (CDK also needs cdk.jar)
extra-clean3d CDPKit conformer engine

CGRtools

Chython is a fork of CGRtools.

Copyright

Contributors

CGRtools contributors are included too.

Project links

Key dates

PyPI data
Data sourced directly from PyPI's database.
  • Released:
Newer release available (3.3.1)

1 maintainer

PyPI data
Data sourced directly from PyPI's database.
Avatar for nougmanoff from gravatar.com nougmanoff

Credits

Author: Ramil Nugmanov

License expression

LGPL-3.0-or-later
View SPDX License List

Requires

Python >=3.10

Provides Extra

ml mapping rdkit extra-clean2d extra-clean3d iupac

Classifiers

Report project as malware

Release files for chython 3.2

For a detailed explanation of source distributions (sdists) and built distributions (wheels), please see the package formats documentation.

Source distribution (sdist)

Source distribution for chython 3.2
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chython-3.2.tar.gz 3.4 MB Details

Built distributions (wheels)

Table of built distributions (wheels) for chython 3.2
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chython-3.2-cp314-cp314-win_amd64.whl 4.9 MB CPython 3.14 CPython 3.14 Windows x86-64 Details
chython-3.2-cp314-cp314-manylinux_2_39_x86_64.whl 5.2 MB CPython 3.14 CPython 3.14 Linux glibc 2.39+ x86-64 Details
chython-3.2-cp314-cp314-manylinux_2_39_aarch64.whl 5.1 MB CPython 3.14 CPython 3.14 Linux glibc 2.39+ ARM64 Details
chython-3.2-cp314-cp314-macosx_10_15_universal2.whl 7.1 MB CPython 3.14 CPython 3.14 macOS 10.15+ universal2 (ARM64, x86-64) Details
chython-3.2-cp313-cp313-win_amd64.whl 4.9 MB CPython 3.13 CPython 3.13 Windows x86-64 Details
chython-3.2-cp313-cp313-manylinux_2_39_x86_64.whl 5.2 MB CPython 3.13 CPython 3.13 Linux glibc 2.39+ x86-64 Details
chython-3.2-cp313-cp313-manylinux_2_39_aarch64.whl 5.1 MB CPython 3.13 CPython 3.13 Linux glibc 2.39+ ARM64 Details
chython-3.2-cp313-cp313-macosx_10_13_universal2.whl 7.1 MB CPython 3.13 CPython 3.13 macOS 10.13+ universal2 (ARM64, x86-64) Details
chython-3.2-cp312-cp312-win_amd64.whl 4.9 MB CPython 3.12 CPython 3.12 Windows x86-64 Details
chython-3.2-cp312-cp312-manylinux_2_39_x86_64.whl 5.2 MB CPython 3.12 CPython 3.12 Linux glibc 2.39+ x86-64 Details
chython-3.2-cp312-cp312-manylinux_2_39_aarch64.whl 5.1 MB CPython 3.12 CPython 3.12 Linux glibc 2.39+ ARM64 Details
chython-3.2-cp312-cp312-macosx_10_13_universal2.whl 7.1 MB CPython 3.12 CPython 3.12 macOS 10.13+ universal2 (ARM64, x86-64) Details
chython-3.2-cp311-cp311-win_amd64.whl 4.9 MB CPython 3.11 CPython 3.11 Windows x86-64 Details
chython-3.2-cp311-cp311-manylinux_2_39_x86_64.whl 5.3 MB CPython 3.11 CPython 3.11 Linux glibc 2.39+ x86-64 Details
chython-3.2-cp311-cp311-manylinux_2_39_aarch64.whl 5.2 MB CPython 3.11 CPython 3.11 Linux glibc 2.39+ ARM64 Details
chython-3.2-cp311-cp311-macosx_10_9_universal2.whl 7.1 MB CPython 3.11 CPython 3.11 macOS 10.9+ universal2 (ARM64, x86-64) Details
chython-3.2-cp310-cp310-win_amd64.whl 4.9 MB CPython 3.10 CPython 3.10 Windows x86-64 Details
chython-3.2-cp310-cp310-manylinux_2_39_x86_64.whl 5.3 MB CPython 3.10 CPython 3.10 Linux glibc 2.39+ x86-64 Details
chython-3.2-cp310-cp310-manylinux_2_39_aarch64.whl 5.2 MB CPython 3.10 CPython 3.10 Linux glibc 2.39+ ARM64 Details
chython-3.2-cp310-cp310-macosx_10_9_universal2.whl 7.1 MB CPython 3.10 CPython 3.10 macOS 10.9+ universal2 (ARM64, x86-64) Details

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3.3.1

21 release files

This release

3.2 This release

21 release files

3.1

21 release files

3.0.2

21 release files

2.24

20 release files

2.22

20 release files

2.21

20 release files

2.20

20 release files

2.19

15 release files

2.18

9 release files

2.17

9 release files

2.16

9 release files

Pre-release

2.15.2a1

9 release files

2.15.1

9 release files

2.13

9 release files

2.12

9 release files

2.11.1

9 release files

2.11

9 release files

2.10

9 release files

2.9.1

9 release files

2.8.1

9 release files

2.7.2

14 release files

2.6

9 release files

2.5

9 release files

2.4

13 release files

2.3

12 release files

1.78

12 release files

1.75

12 release files

1.70

16 release files

1.68

7 release files

1.64.1

1 release file

1.64

6 release files

1.57

7 release files

1.54

7 release files

1.48.1

7 release files

1.45

7 release files

1.44

4 release files

1.42

1 release file

1.41

1 release file

1.38

1 release file

1.36

1 release file

1.34

1 release file

1.33

1 release file

1.31

1 release file

1.27

1 release file

1.23

1 release file

1.22

1 release file

1.20

1 release file

1.19

1 release file

1.17

1 release file

1.16.1

1 release file

1.15

1 release file

1.11.1

1 release file

1.10

1 release file

1.8

1 release file

1.6

1 release file

1.1

1 release file

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