catechin   Click here for help

GtoPdb Ligand ID: 13091

Synonyms: (+)-catechin | catechol | cianidanol | D-Catechin
PDB Ligand
Compound class: Natural product
Comment: Catechin is a plant-derived flavonoid (from Acacia catechu, and cacao, grapes and tea plants). This entry represents the 2R,3S diastereoisomer, but 3 others are possible given that the molecule has two chiral centers. Catechin has relatively low antioxidant properties compared to other flavonoids.

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 1
Topological polar surface area 110.38
Molecular weight 290.27
XLogP 0.58
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C1=C(C=C(C(=C1)O)O)[C@@H]2[C@H](CC3=C(C=C(C=C3O)O)O2)O
Isomeric SMILES C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
InChI InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
InChI Key PFTAWBLQPZVEMU-DZGCQCFKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms Click here for help
(+)-catechin | catechol | cianidanol | D-Catechin
Database Links Click here for help
BindingDB Ligand 60836
ChEMBL Ligand CHEMBL311498
DrugBank Ligand DB14086
GtoPdb PubChem SID 491299873
LIPID MAPS LMPK12020001
PubChem CID 9064
RCSB PDB Ligand KXN
Search Google for chemical match using the InChIKey PFTAWBLQPZVEMU-DZGCQCFKSA-N
Search Google for chemicals with the same backbone PFTAWBLQPZVEMU
UniChem Compound Search for chemical match using the InChIKey PFTAWBLQPZVEMU-DZGCQCFKSA-N
UniChem Connectivity Search for chemical match using the InChIKey PFTAWBLQPZVEMU-DZGCQCFKSA-N

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MedChemExpress
(±)-Catechin (links to external site)
Cat. No. HY-B1890
Catechin (links to external site)
Cat. No. HY-N0898