3,5-di-O-caffeoyl quinic acid (CHEBI:65751)

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CHEBI:65751 - 3,5-di-O-caffeoyl quinic acid

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ChEBI ID	CHEBI:65751
ChEBI Name	3,5-di-O-caffeoyl quinic acid
Stars
ASCII Name	3,5-di-O-caffeoyl quinic acid
Definition	A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (−)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.
Last Modified	7 November 2024
Downloads	Molfile

Formula	C25H24O12
Net Charge	0
Average Mass	516.455
Monoisotopic Mass	516.12678
SMILES	O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H]1O
InChI	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
InChIKey	KRZBCHWVBQOTNZ-PSEXTPKNSA-N

Species of Metabolite	Component	Source	Comments
Dichrocephala bicolor (IPNI:201282-1)	whole plant (BTO:0001461)	DOI (10.1021/np980153o)
Apis mellifera (ncbitaxon:7460)	-	PubMed (8951168)	Found in propolis.
Solidago virgaaurea var. gigantea (ncbitaxon:462879)	aerial part (BTO:0001658)	PubMed (15022716)
Suaeda glauca (ncbitaxon:397272)	whole plant (BTO:0001461)	PubMed (18481014)
Phagnalon rupestre (ncbitaxon:943712)	aerial part (BTO:0001658)	PubMed (21469692)	Ethyl acetate soluble fraction from methanolic extract of aerial parts

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. hepatoprotective agent Any compound that is able to prevent damage to the liver.

ChEBI Ontology

Outgoing Relation(s)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent (−)-quinic acid (CHEBI:17521)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent trans-caffeic acid (CHEBI:16433)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role antineoplastic agent (CHEBI:35610)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role hepatoprotective agent (CHEBI:62868)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role metabolite (CHEBI:25212)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) is a carboxylic ester (CHEBI:33308)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) is a cyclitol carboxylic acid (CHEBI:36123)
	3,5-di-O-caffeoyl quinic acid (CHEBI:65751) is conjugate acid of 3,5-di-O-caffeoyl quinate (CHEBI:231591)
Incoming Relation(s)
	methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has functional parent 3,5-di-O-caffeoyl quinic acid (CHEBI:65751)
	3,5-di-O-caffeoyl quinate (CHEBI:231591) is conjugate base of 3,5-di-O-caffeoyl quinic acid (CHEBI:65751)

IUPAC Name
(3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid

Synonyms	Source
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate	ChEBI
Quinic acid 3,5-di-O-caffeate	HMDB
3,5-DCQA	HMDB
Isochlorogenic acid a	HMDB
3,5-Dicaffeoylquinic acid	HMDB

Manual Xrefs	Databases
HMDB0030706	HMDB

Registry Numbers	Sources
Reaxys:4895191	Reaxys

Citations