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CHEBI:38300 - (−)-vernolic acid

ChEBI IDCHEBI:38300
ChEBI Name(−)-vernolic acid
Stars
ASCII Name(-)-vernolic acid
DefinitionAn optically active form of vernolic acid having (12R,13S)-configuration.
Last Modified9 March 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC18H32O3
Net Charge0
Average Mass296.451
Monoisotopic Mass296.23514
SMILESCCCCC[C@@H]1O[C@@H]1C/C=C\CCCCCCCC(=O)O
InChIInChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1
InChIKeyCCPPLLJZDQAOHD-BEBBCNLGSA-N
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
(−)-vernolic acid (CHEBI:38300) is a vernolic acid (CHEBI:38299)
(−)-vernolic acid (CHEBI:38300) is conjugate acid of (−)-vernolate (CHEBI:194416)
(−)-vernolic acid (CHEBI:38300) is enantiomer of (+)-vernolic acid (CHEBI:27706)
Incoming Relation(s)
(−)-vernolate (CHEBI:194416) is conjugate base of (−)-vernolic acid (CHEBI:38300)
(+)-vernolic acid (CHEBI:27706) is enantiomer of (−)-vernolic acid (CHEBI:38300)
IUPAC Name 
(9Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoic acid
Synonyms  Source
(9Z)-(12R,13S)-12,13-epoxyoctadecenoic acidChEBI
(−)-VernolsäureChEBI
(−)-leukotoxin BChEBI
(−)-12(R),13(S)-vernolic acidChEBI
cis-12S,13R,-ep, 9c-18:1ChEBI
12,13-epoxylinoleic acidChEBI
Manual XrefsDatabases
C00001241KNApSAcK
T25PDBeChem
C08368KEGG COMPOUND
C14826KEGG COMPOUND
Registry NumbersSources
Reaxys:86881Reaxys
CAS:503-07-1KEGG COMPOUND
Citations