appears_in: []
contact:
  email: tim.vandermeersch@gmail.com
  github: timvdm
  name: Tim Vandermeersch
contributor:
  email: cthoyt@gmail.com
  github: cthoyt
  name: Charles Tapley Hoyt
  orcid: 0000-0003-4423-4370
contributor_extras:
- github: NishaSharma14
  name: Nisha Sharma
  orcid: 0009-0006-4755-1039
depends_on: []
deprecated: false
description: Documentation of SMILES (Simplified Molecular Input Line Entry System),
  a line notation (a typographical method using printable characters) for entering
  and representing molecules and reactions.
example: CC2(C)C\1CCC(C)/C=C/12
example_extras: []
homepage: https://www.daylight.com/dayhtml/doc/theory/theory.smiles.html
keywords:
- chemistry
- life science
mappings:
  fairsharing: FAIRsharing.qv4b3c
  wikidata: P233
name: Simplified molecular-input line-entry system
pattern: ^[A-Za-z0-9+\-\*=#$:().>/\\\[\]%]+$
preferred_prefix: smiles
prefix: smiles
providers:
- code: cms.canonicalize
  description: Canonicalizes a given SMILES string according to the allowed toolkits.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_Canonicalise_convert_canonicalsmiles_get
  name: Canonicalizes a SMILES via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/canonicalsmiles?smiles=$1
- code: cms.convert
  description: Convert SMILES to various molecular formats using different toolkits.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_convert_to_Formats_convert_formats_get
  name: Convert SMILES to various molecular formats via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/formats?smiles=$1
- code: cms.coordinates2d
  description: Generates 2D Coordinates using the CDK Structure diagram generator/RDKit/Open
    Babel and returns the mol block.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/Create2D_Coordinates_convert_mol2D_get
  name: Generate 2D coordinates via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/mol2D?smiles=$1
- code: cms.coordinates3d
  description: Generates a random 3D conformer from SMILES using the specified molecule
    toolkit.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/Create3D_Coordinates_convert_mol3D_get
  name: Generate 3D conformer via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/mol3D?smiles=$1
- code: cms.cxsmiles
  description: Convert SMILES to CXSMILES. For more informations.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_to_CXSMILES_convert_cxsmiles_get
  name: Convert SMILES to CXSMILES via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/cxsmiles?smiles=$1
- code: cms.depict2d
  description: Generates a 2D depiction of a molecule using CDK or RDKit with the
    given parameters.
  homepage: https://api.naturalproducts.net/latest/docs#/depict/Depict2D_molecule_depict_2D_get
  name: Depict 2D via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/depict/2D?smiles=$1
- code: cms.depict3d
  description: Generate 3D depictions of molecules using OpenBabel or RDKit.
  homepage: https://api.naturalproducts.net/latest/docs#/depict/Depict3D_Molecule_depict_3D_get
  name: Depict 3D via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/depict/3D?smiles=$1
- code: cms.descriptor
  description: Returns descriptors calculated from the molecule with RDKit
  homepage: https://api.naturalproducts.net/latest/docs#/chem/get_descriptors_chem_descriptors_get
  name: RDKit Descriptor via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/chem/descriptors?smiles=$1
- code: cms.inchi
  description: Convert SMILES to InChI.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_to_InChI_convert_inchi_get
  name: Convert SMILES to InChI via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/inchi?smiles=$1
- code: cms.inchikey
  description: Convert SMILES to InChIKey.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_to_InChIKey_convert_inchikey_get
  name: Convert SMILES to InChIKey via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/inchikey?smiles=$1
- code: cms.iupac
  description: Generates IUPAC name for given SMILES using [STOUT](https://jcheminf.biomedcentral.com/articles/10.1186/s13321-021-00512-4)
    package.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/SMILES_to_IUPACname_convert_iupac_get
  name: Generate IUPAC name from SMILES via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/iupac?smiles=$1
- code: cms.selfies
  description: Generates SELFIES string for a given SMILES string.
  homepage: https://api.naturalproducts.net/latest/docs#/convert/encode_SELFIES_convert_selfies_get
  name: Generates SELFIES for a SMILES via the Cheminformatics Microservice
  uri_format: https://api.naturalproducts.net/latest/convert/selfies?smiles=$1
publications:
- doi: 10.1186/1758-2946-4-24
  pmc: PMC3551648
  pubmed: '23031664'
  title: mol2chemfig, a tool for rendering chemical structures from molfile or SMILES
    format to LATE X code
  year: 2012
- doi: 10.1021/ci00067a005
  title: SMILES. 3. DEPICT. Graphical depiction of chemical structures
  year: 1990
- doi: 10.1021/ci00062a008
  title: SMILES. 2. Algorithm for generation of unique SMILES notation
  year: 1989
- doi: 10.1021/ci00057a005
  title: SMILES, a chemical language and information system. 1. Introduction to methodology
    and encoding rules
  year: 1988
references:
- https://github.com/biopragmatics/bioregistry/issues/931
repository: https://github.com/timvdm/OpenSMILES/blob/master/discussion_summary.txt
synonyms: []
uri_format: https://www.simolecule.com/cdkdepict/depict/bow/svg?smi=$1&zoom=2.0&annotate=cip
