CHEBI:138434 - 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
ChEBI ID CHEBI:138434
ChEBI ASCII Name 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
Definition A carbocyclic fatty acid that is cyclopent-2-en-1-one which has been substituted at positions 4 and 5 by 5-carboxypentyl and (2ZZ)-pent-2-en-1-yl groups, respectively (the S,S stereoisomer). It is an intermediate in the synthesis of jasmonic acid from hexadecatrienoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H24O3
Net Charge 0
Average Mass 264.361
Monoisotopic Mass 264.17254
InChI InChI=1S/C16H24O3/c1-2-3-5-9-14-13(11-12-15(14)17)8-6-4-7-10-16(18)19/h3,5,11-14H,2,4,6-10H2,1H3,(H,18,19)/b5-3-/t13-,14-/m0/s1
InChIKey SZVNKXCDJUBPQO-DWMAKUKJSA-N
SMILES C=1C([C@@H](C/C=C\CC)[C@H](C1)CCCCCC(=O)O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434) is a carbocyclic fatty acid (CHEBI:35744)
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434) is a enone (CHEBI:51689)
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434) is a oxo fatty acid (CHEBI:59644)
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434) is a polyunsaturated fatty acid (CHEBI:26208)
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434) is conjugate acid of 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoate (CHEBI:138432)
Incoming (9S,13S)-1a,1b-dinor-12-oxo-10,15-phytodienoyl-CoA (CHEBI:139107) has functional parent 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434)
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoate (CHEBI:138432) is conjugate base of 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid (CHEBI:138434)
IUPAC Name
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
Synonyms Sources
(S,S,Z)-dinor-12-oxo PDA ChEBI
(S,S,Z)-dinor-12-oxo-phytodienoic acid ChEBI
(S,S,Z)-dinor-OPDA ChEBI
4-oxo-5S-(2Z)-2-penten-1-yl-2-cyclopentene-1S-hexanoic acid ChEBI
dinor-12-oxo PDA ChEBI
Registry Number Type Source
197247-23-7 CAS Registry Number ChEBI
Citation Waiting for Citations Type Source
9294235 PubMed citation Europe PMC
Last Modified
20 November 2017