EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65637 - citrifolinoside

ChEBI IDCHEBI:65637
ChEBI Namecitrifolinoside
Stars
DefinitionAn 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.
Last Modified16 March 2015
DownloadsMolfile
FormulaC28H30O15
Net Charge0
Average Mass606.533
Monoisotopic Mass606.15847
SMILES[H][C@]12O[C@@]1([H])[C@]1([H])C(C(=O)OC)=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC)[C@]1([H])[C@]21C=C(C(=O)c2ccc(OC)c(O)c2)C(=O)O1
InChIInChI=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
InChIKeyNUMSWUCLFNXPFE-WVQLPIEPSA-N
Species of MetaboliteComponentSourceComments
Morinda citrifolia (ncbitaxon:43522) leaf (BTO:0000713) PubMed (11348221)
Roles Classification
Biological Roles:
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).
ChEBI Ontology
Outgoing Relation(s)
citrifolinoside (CHEBI:65637) has role AP-1 antagonist (CHEBI:67199)
citrifolinoside (CHEBI:65637) has role metabolite (CHEBI:25212)
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)
citrifolinoside (CHEBI:65637) is a β-D-glucoside (CHEBI:22798)
citrifolinoside (CHEBI:65637) is a γ-lactone (CHEBI:37581)
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