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CHEBI:66708 - methyl 3,5-di-O-caffeoyl quinate

ChEBI IDCHEBI:66708
ChEBI Namemethyl 3,5-di-O-caffeoyl quinate
Stars
ASCII Namemethyl 3,5-di-O-caffeoyl quinate
DefinitionA methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.
Last Modified6 March 2015
DownloadsMolfile
FormulaC26H26O12
Net Charge0
Average Mass530.482
Monoisotopic Mass530.14243
SMILESCOC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/c2ccc(O)c(O)c2)[C@@H](O)[C@H](OC(=O)/C=C/c2ccc(O)c(O)c2)C1
InChIInChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24-,26+/m1/s1
InChIKeyVEBNYMXKXIIGFX-VOHNXBSUSA-N
Species of MetaboliteComponentSourceComments
Solidago virgaaurea var. gigantea (ncbitaxon:462879) aerial part (BTO:0001658) PubMed (15022716)
Suaeda glauca (ncbitaxon:397272) whole plant (BTO:0001461) PubMed (18481014)
Dichrocephala bicolor (IPNI:201282-1) whole plant (BTO:0001461) DOI (10.1021/np980153o)
Phagnalon rupestre (ncbitaxon:943712) aerial part (BTO:0001658) PubMed (21469692) Ethyl acetate soluble fraction from methanolic extract of aerial parts
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
ChEBI Ontology
Outgoing Relation(s)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has functional parent 3,5-di-O-caffeoyl quinic acid (CHEBI:65751)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has role hepatoprotective agent (CHEBI:62868)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has role metabolite (CHEBI:25212)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a catechols (CHEBI:33566)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a cinnamate ester (CHEBI:36087)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a methyl ester (CHEBI:25248)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a secondary alcohol (CHEBI:35681)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
methyl (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylate
Manual XrefsDatabases
24692051ChemSpider
Registry NumbersSources
Reaxys:9172717Reaxys
Citations