CHEBI:136555 - 1-O-caffeoylquinic acid

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ChEBI Name 1-O-caffeoylquinic acid
ChEBI ID CHEBI:136555
ChEBI ASCII Name 1-O-caffeoylquinic acid
Definition An alkyl caffeate ester obtained by the formal condensation of the carboxy group of trans-caffeic acid with the 1-hydroxy group of (−)-quinic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H18O9
Net Charge 0
Average Mass 354.309
Monoisotopic Mass 354.09508
InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+/t11-,12-,14-,16+/m1/s1
InChIKey GWTUHAXUUFROTF-JUHZACGLSA-N
SMILES C(=O)(/C=C/C1=CC=C(O)C(O)=C1)O[C@@]2(C[C@@H](O)[C@@H]([C@@H](C2)O)O)C(O)=O
Metabolite of Species Details
Tetrastigma hemsleyanum (NCBI:txid1006121) Found in leaf (BTO:0000713). See: PubMed
Lonicera japonica (NCBI:txid105884) Found in flower bud (BTO:0000470). See: PubMed
Cyclocarya paliurus (NCBI:txid117167) Found in leaf (BTO:0000713). See: DOI
Xanthium (NCBI:txid36590) Found in fruit (BTO:0000486). See: PubMed
Camellia sinensis (NCBI:txid4442) See: MetaboLights Study
Canna edulis (NCBI:txid4628) Obtained from water-soluble extracts See: DOI
Cynara cardunculus var. scolymus (NCBI:txid59895) See: PubMed
Crepidiastrum sonchifolium (NCBI:txid77563) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Camellia sinensis metabolite
Any plant metabolite that is produced by Camellia sinensis.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via quinic acid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 1-O-caffeoylquinic acid (CHEBI:136555) has functional parent trans-caffeic acid (CHEBI:16433)
1-O-caffeoylquinic acid (CHEBI:136555) has parent hydride (−)-quinic acid (CHEBI:17521)
1-O-caffeoylquinic acid (CHEBI:136555) has role Camellia sinensis metabolite (CHEBI:140160)
1-O-caffeoylquinic acid (CHEBI:136555) has role antineoplastic agent (CHEBI:35610)
1-O-caffeoylquinic acid (CHEBI:136555) has role antioxidant (CHEBI:22586)
1-O-caffeoylquinic acid (CHEBI:136555) has role NF-κB inhibitor (CHEBI:73240)
1-O-caffeoylquinic acid (CHEBI:136555) is a alkyl caffeate ester (CHEBI:65331)
1-O-caffeoylquinic acid (CHEBI:136555) is a quinic acid (CHEBI:26493)
IUPAC Name
(1S,3R,4S,5R)-1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylic acid
Synonyms Sources
1-Caffeoylquinic acid ChemIDplus
1-O-(trans-caffeoyl)quinic acid ChEBI
trans-1-o-Caffeoylquinic acid ChemIDplus
Registry Numbers Types Sources
3173163 Reaxys Registry Number Reaxys
928005-87-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15884803 PubMed citation Europe PMC
18830958 PubMed citation Europe PMC
19185132 PubMed citation Europe PMC
23661994 PubMed citation Europe PMC
24151872 PubMed citation Europe PMC
24228586 PubMed citation Europe PMC
28873750 PubMed citation Europe PMC
IND44292559 Agricola citation Europe PMC
IND44619880 Agricola citation Europe PMC
Last Modified
15 February 2018