CHEBI:131781 - vibsanin B

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ChEBI Name vibsanin B
ChEBI ID CHEBI:131781
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H36O5
Net Charge 0
Average Mass 416.551
Monoisotopic Mass 416.25627
InChI InChI=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
InChIKey GYXPHGPELZUVGI-QYGPLFBNSA-N
SMILES C1=CC(C(=CC[C@@](C=C[C@]([C@@]1(O)C)(OC(=O)C=C(C)C)[H])(CCC=C(C)C)C)CO)=O
Metabolite of Species Details
Viburnum suspensum (NCBI:txid237958) Found in leaf (BTO:0000713). See: PubMed
Viburnum awabuki (NCBI:txid453244) Found in leaf (BTO:0000713). https://www.jstage.jst.go.jp/article/bbb1961/44/6/44_6_1367/_pdf See: Kawazu, K., 1980. Isolation of vibsanins A, B, C, D, E, and F from Viburnum odoratissimum . Agric. Biol. Chem. 44, 1367–1372.
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
plant growth retardant

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ChEBI Ontology
Outgoing 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 B ChEBI
Registry Number Type Source
7831954 Reaxys Registry Number Reaxys
Last Modified
20 April 2016