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

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ChEBI Name gelsemiol-6'-trans-caffeoyl-1-glucoside
ChEBI ID CHEBI:65957
ChEBI ASCII Name gelsemiol-6'-trans-caffeoyl-1-glucoside
Definition A iridoid monoterpenoid isolated from the aerial parts of Verbena litoralis and shown to possess stimulating effects on nerve growth factor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H32O12
Net Charge 0
Average Mass 524.51440
Monoisotopic Mass 524.18938
InChI InChI=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
InChIKey RLIILNKNNUJZAL-HPBWOJKHSA-N
SMILES [H][C@]12C[C@H](C)[C@@H](CO[C@@H]3O[C@H](COC(=O)\C=C\c4ccc(O)c(O)c4)[C@@H](O)[C@H](O)[C@H]3O)[C@@]1([H])[C@H](CO)C(=O)O2
Metabolite of Species Details
Verbena litoralis (NCBI:txid443384) Found in aerial part (BTO:0001658). 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.
nerve growth factor stimulator
Any molecule shown to have the potentiality in stimulating the effect of nerve growth factor.
Application(s): nerve growth factor stimulator
Any molecule shown to have the potentiality in stimulating the effect of nerve growth factor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) is a γ-lactone (CHEBI:37581)
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)
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 Number Type Source
9601910 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12951458 PubMed citation Europe PMC
Last Modified
07 February 2013