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CHEBI:131781 - vibsanin B

ChEBI IDCHEBI:131781
ChEBI Namevibsanin B
Stars
DefinitionA vibsane diterpenoid that is (2Z,6E,10E)-cycloundeca-2,6,10-trien-1-one which is substituted at positions 2, 5, 5, 8, 9, and 9 by hydroxymethyl, methyl, 2-methylpent-2-en-5-yl, 3-methylbut-2-enoyloxy, hydroxy, and methyl groups, respectively (the 5S,8R,9R stereoisomer). It has been found to inhibit root growth in rice seedlings (IC50 0.14 mM).
Last Modified20 April 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H36O5
Net Charge0
Average Mass416.558
Monoisotopic Mass416.25627
SMILES[H][C@@]1(OC(=O)C=C(C)C)/C=C/[C@@](C)(CCC=C(C)C)C/C=C(/CO)C(=O)/C=C/[C@@]1(C)O
InChIInChI=1S/C25H36O5/c1-18(2)8-7-12-24(5)13-9-20(17-26)21(27)10-15-25(6,29)22(11-14-24)30-23(28)16-19(3)4/h8-11,14-16,22,26,29H,7,12-13,17H2,1-6H3/b14-11+,15-10+,20-9-/t22-,24+,25-/m1/s1
InChIKeyGYXPHGPELZUVGI-QYGPLFBNSA-N
Species of MetaboliteComponentSourceComments
Viburnum awabuki (ncbitaxon:453244) leaf (BTO:0000713) Article (Kawazu, K., 1980. Isolation of vibsanins A, B, C, D, E, and F from Viburnum odoratissimum . Agric. Biol. Chem. 44, 1367–1372.) https://www.jstage.jst.go.jp/article/bbb1961/44/6/44_6_1367/_pdf
Viburnum suspensum (ncbitaxon:237958) leaf (BTO:0000713) PubMed (12150795)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
vibsanin B (CHEBI:131781) has functional parent 3-methylbut-2-enoic acid (CHEBI:37127)
vibsanin B (CHEBI:131781) has role plant growth retardant (CHEBI:35219)
vibsanin B (CHEBI:131781) has role plant metabolite (CHEBI:76924)
vibsanin B (CHEBI:131781) is a cyclic terpene ketone (CHEBI:36130)
vibsanin B (CHEBI:131781) is a enone (CHEBI:51689)
vibsanin B (CHEBI:131781) is a tertiary alcohol (CHEBI:26878)
vibsanin B (CHEBI:131781) is a vibsane diterpenoid (CHEBI:131782)
IUPAC Name 
(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate
Synonym  Source
vibsanine BChEBI
Registry NumbersSources
Reaxys:7831954Reaxys