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CHEBI:66499 - yuccalan

ChEBI IDCHEBI:66499
ChEBI Nameyuccalan
Stars
DefinitionA spirostanyl glycoside that is (3β,5α,6α,25S)-spirostan-3,6,27-triol attached to a 6-O-β-D-glucopyranosyl-β-D-glucopyranosyl residue via a glycosidic linkage. Isolated from Yucca smalliana, it exhibits antifungal activity.
Last Modified15 July 2013
DownloadsMolfile
FormulaC39H64O15
Net Charge0
Average Mass772.926
Monoisotopic Mass772.42452
SMILES[H][C@@]1(OC[C@H]2O[C@@]([H])(O[C@H]3CC[C@]4(C)[C@@]5([H])CC[C@@]6(C)[C@@]([H])(C[C@]7([H])O[C@]8(CC[C@@H](CO)CO8)[C@@H](C)[C@]67[H])[C@]5([H])C[C@H](O)[C@@]4([H])C3)[C@H](O)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C39H64O15/c1-17-28-25(54-39(17)9-4-18(13-40)15-50-39)12-22-20-11-24(42)23-10-19(5-7-37(23,2)21(20)6-8-38(22,28)3)51-36-34(48)32(46)30(44)27(53-36)16-49-35-33(47)31(45)29(43)26(14-41)52-35/h17-36,40-48H,4-16H2,1-3H3/t17-,18-,19-,20+,21-,22-,23+,24-,25-,26+,27+,28-,29+,30+,31-,32-,33+,34+,35+,36+,37+,38-,39+/m0/s1
InChIKeyALKMFECERUDLEI-UBXCSCSKSA-N
Species of MetaboliteComponentSourceComments
Yucca smalliana (IPNI:270423-2) leaf (BTO:0000713) PubMed (17615670)
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.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
yuccalan (CHEBI:66499) has parent hydride (25S)-5α-spirostan (CHEBI:74686)
yuccalan (CHEBI:66499) has role antifungal agent (CHEBI:35718)
yuccalan (CHEBI:66499) has role metabolite (CHEBI:25212)
yuccalan (CHEBI:66499) is a 27-hydroxy steroid (CHEBI:37914)
yuccalan (CHEBI:66499) is a 6α-hydroxy steroid (CHEBI:36850)
yuccalan (CHEBI:66499) is a disaccharide derivative (CHEBI:63353)
yuccalan (CHEBI:66499) is a organic heterohexacyclic compound (CHEBI:51914)
yuccalan (CHEBI:66499) is a oxaspiro compound (CHEBI:37948)
yuccalan (CHEBI:66499) is a spirostanyl glycoside (CHEBI:38091)
IUPAC Name 
(3β,5α,6α,25S)-6,27-dihydroxyspirostan-3-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside
Synonym  Source
3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(3β, 5α, 6α, 25S)-spirostan-3,6,27-triolChEBI
Citations