CHEBI:132826 - versicolactone B

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ChEBI Name versicolactone B
ChEBI ID CHEBI:132826
Definition A sesquiterpene lactone with formula C15H22O3 that is isolated from Viola yedoensis and Aristolochia versicolor.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Supplier Information
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Formula C15H22O3
Net Charge 0
Average Mass 250.334
Monoisotopic Mass 250.15689
InChI InChI=1S/C15H22O3/c1-9(2)12-6-4-10(3)13(16)7-5-11-8-14(12)18-15(11)17/h4,11-14,16H,1,5-8H2,2-3H3/b10-4+/t11-,12-,13+,14-/m1/s1
InChIKey COEDSYSRVAUHQU-GEHWQCAJSA-N
SMILES [C@H]1([C@]2(C[C@H](C(O2)=O)CC[C@@H](C(=CC1)C)O)[H])C(C)=C
Metabolite of Species Details
Aristolochia versicolar (NCBI:txid1523942) Found in root (BTO:0001188). See: PubMed
Viola yedoensis (NCBI:txid316493) Found in leaf (BTO:0000713). See: PubMed
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.
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ChEBI Ontology
Outgoing versicolactone B (CHEBI:132826) has role plant metabolite (CHEBI:76924)
versicolactone B (CHEBI:132826) is a germacrane sesquiterpenoid (CHEBI:68588)
versicolactone B (CHEBI:132826) is a olefinic compound (CHEBI:78840)
versicolactone B (CHEBI:132826) is a oxabicycloalkane (CHEBI:46733)
versicolactone B (CHEBI:132826) is a secondary alcohol (CHEBI:35681)
versicolactone B (CHEBI:132826) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name
(1R,4S,5E,8R,9R)-4-hydroxy-5-methyl-8-(prop-1-en-2-yl)-10-oxabicyclo[7.2.1]dodec-5-en-11-one
Manual Xref Database
C00033470 KNApSAcK
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Registry Numbers Types Sources
104613-44-7 CAS Registry Number ChemIDplus
27710224 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
25562805 PubMed citation Europe PMC
3788595 PubMed citation Europe PMC
Last Modified
24 January 2017