chlorogenic acid   Click here for help

GtoPdb Ligand ID: 12477

Synonyms: 3-O-caffeoylquinic acid | caffeoyl quinic acid | chlorogenate
Comment: Chlorogenic acid is a natural product that is present in coffee and black tea and some other plants. Chemically it is a caffeic acid-quinic acid ester. It has been attributed with several biological activities, including antioxidant, anti-carcinogenic and immunomodulatory effects [1-3,5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 164.75
Molecular weight 354.31
XLogP -0.97
No. Lipinski's rules broken 1
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Canonical SMILES C1=C(/C=C/C(=O)O[C@@H]2C[C@@](C[C@H]([C@H]2O)O)(C(=O)O)O)C=C(C(=C1)O)O
Isomeric SMILES C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Synonyms Click here for help
3-O-caffeoylquinic acid | caffeoyl quinic acid | chlorogenate
Database Links Click here for help
BindingDB Ligand 13080
CAS Registry No. 327-97-9 (source: PubChem)
ChEMBL Ligand CHEMBL284616
GtoPdb PubChem SID 479821267
PubChem CID 1794427
Search Google for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N
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UniChem Compound Search for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N
UniChem Connectivity Search for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N