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

ChEBI IDCHEBI:138434
ChEBI Name6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
Stars
ASCII Name6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
DefinitionA 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.
Last Modified20 November 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H24O3
Net Charge0
Average Mass264.365
Monoisotopic Mass264.17254
SMILESCC/C=C\C[C@@H]1C(=O)C=C[C@@H]1CCCCCC(=O)O
InChIInChI=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
InChIKeySZVNKXCDJUBPQO-DWMAKUKJSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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  Source
4-oxo-5S-(2Z)-2-penten-1-yl-2-cyclopentene-1S-hexanoic acidChEBI
dinor-12-oxo PDAChEBI
(S,S,Z)-dinor-12-oxo-phytodienoic acidChEBI
(S,S,Z)-dinor-12-oxo PDAChEBI
(S,S,Z)-dinor-OPDAChEBI
Registry NumbersSources
CAS:197247-23-7ChEBI
Citations