CHEBI:65637 - citrifolinoside

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ChEBI Name citrifolinoside
ChEBI ID CHEBI:65637
Definition An unusual iridoid monoterpenoid isolated from the leaves of Morinda citrifolia. It exhibits significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H30O15
Net Charge 0
Average Mass 606.52880
Monoisotopic Mass 606.15847
InChI InChI=1S/C28H30O15/c1-36-14-5-4-10(6-13(14)30)18(31)11-7-28(43-25(11)35)17-16(21-23(28)41-21)12(24(34)38-3)9-39-26(17)42-27-22(37-2)20(33)19(32)15(8-29)40-27/h4-7,9,15-17,19-23,26-27,29-30,32-33H,8H2,1-3H3/t15-,16-,17-,19-,20+,21+,22-,23+,26+,27+,28-/m1/s1
InChIKey NUMSWUCLFNXPFE-WVQLPIEPSA-N
SMILES CO[C@H]1[C@H](O[C@@H]2OC=C([C@H]3[C@@H]4O[C@@H]4[C@]4(OC(=O)C(=C4)C(=O)c4ccc(OC)c(O)c4)[C@@H]23)C(=O)OC)O[C@H](CO)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Morinda citrifolia (NCBI:txid43522) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
AP-1 antagonist
An antogonist that interferes with the action of activator protein 1 (AP-1).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing citrifolinoside (CHEBI:65637) has role AP-1 antagonist (CHEBI:67199)
citrifolinoside (CHEBI:65637) has role metabolite (CHEBI:25212)
citrifolinoside (CHEBI:65637) is a β-D-glucoside (CHEBI:22798)
citrifolinoside (CHEBI:65637) is a γ-lactone (CHEBI:37581)
citrifolinoside (CHEBI:65637) is a aromatic ether (CHEBI:35618)
citrifolinoside (CHEBI:65637) is a aromatic ketone (CHEBI:76224)
citrifolinoside (CHEBI:65637) is a enone (CHEBI:51689)
citrifolinoside (CHEBI:65637) is a epoxide (CHEBI:32955)
citrifolinoside (CHEBI:65637) is a iridoid monoterpenoid (CHEBI:50563)
citrifolinoside (CHEBI:65637) is a methyl ester (CHEBI:25248)
citrifolinoside (CHEBI:65637) is a oxaspiro compound (CHEBI:37948)
citrifolinoside (CHEBI:65637) is a phenols (CHEBI:33853)
IUPAC Name
methyl (1a'S,1b'S,2R,5'S,5a'S,6a'S)-5'-(β-D-glucopyranosyloxy)-4-(3-hydroxy-4-methoxybenzoyl)-5-oxo-1a',5',5a',6a'-tetrahydro-1b'H,5H-spiro[furan-2,6'-oxireno[3,4]cyclopenta[1,2-c]pyran]-2'-carboxylate
Citations Waiting for Citations Types Sources
11348221 PubMed citation Europe PMC
17078712 PubMed citation Europe PMC
Last Modified
16 March 2015
General Comment
2012-12-12 Citrifolinoside and yopaaoside A were found to be identical, and their structures were revised as shown: Org Lett.2006, 8(23), 5337-40.