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CHEBI:65957 - gelsemiol-6'-trans-caffeoyl-1-glucoside

ChEBI IDCHEBI:65957
ChEBI Namegelsemiol-6'-trans-caffeoyl-1-glucoside
Stars
ASCII Namegelsemiol-6'-trans-caffeoyl-1-glucoside
DefinitionA iridoid monoterpenoid isolated from the aerial parts of Verbena litoralis and shown to possess stimulating effects on nerve growth factor.
Last Modified7 February 2013
DownloadsMolfile
FormulaC25H32O12
Net Charge0
Average Mass524.519
Monoisotopic Mass524.18938
SMILES[H][C@]12[C@H](CO)C(=O)O[C@@]1([H])C[C@H](C)[C@H]2CO[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(O)c(O)c2)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C25H32O12/c1-11-6-17-20(13(8-26)24(33)36-17)14(11)9-35-25-23(32)22(31)21(30)18(37-25)10-34-19(29)5-3-12-2-4-15(27)16(28)7-12/h2-5,7,11,13-14,17-18,20-23,25-28,30-32H,6,8-10H2,1H3/b5-3+/t11-,13-,14+,17-,18+,20+,21+,22-,23+,25+/m0/s1
InChIKeyRLIILNKNNUJZAL-HPBWOJKHSA-N
Species of MetaboliteComponentSourceComments
Verbena litoralis (ncbitaxon:443384) aerial part (BTO:0001658) PubMed (12951458)
Roles Classification
Biological Roles:
nerve growth factor stimulator  Any molecule shown to have the potentiality in stimulating the effect of nerve growth factor.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
nerve growth factor stimulator  Any molecule shown to have the potentiality in stimulating the effect of nerve growth factor.
ChEBI Ontology
Outgoing Relation(s)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has functional parent trans-caffeic acid (CHEBI:16433)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has role metabolite (CHEBI:25212)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has role nerve growth factor stimulator (CHEBI:72294)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a cinnamate ester (CHEBI:36087)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a iridoid monoterpenoid (CHEBI:50563)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a monoterpene glycoside (CHEBI:72293)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a β-D-glucoside (CHEBI:22798)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a γ-lactone (CHEBI:37581)
IUPAC Name 
[(3R,3aS,4R,5S,6aS)-3-(hydroxymethyl)-5-methyl-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl]methyl 6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Registry NumbersSources
Reaxys:9601910Reaxys
Citations