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chlorogenic acid   Click here for help

GtoPdb Ligand ID: 12477

Synonyms: 3-O-caffeoylquinic acid | caffeoyl quinic acid | chlorogenate
PDB Ligand
Compound class: Natural product
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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Ligand Activity Visualisation Charts

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View interactive charts of activity data across species

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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 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

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(=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
InChI Key CWVRJTMFETXNAD-JUHZACGLSA-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
(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)
ChEBI CHEBI:16112
ChEMBL Ligand CHEMBL284616
GtoPdb PubChem SID 479821267
PubChem CID 1794427
RCSB PDB Ligand A1EG7
Search Google for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N
Search Google for chemicals with the same backbone CWVRJTMFETXNAD
UniChem Compound Search for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N
UniChem Connectivity Search for chemical match using the InChIKey CWVRJTMFETXNAD-JUHZACGLSA-N

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MedChemExpress
Chlorogenic acid (links to external site)
Cat. No. HY-N0055