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MetaCyc Compound: 2-oxopent-4-enoate

Synonyms: 2-oxo-4-pentenoate, 2-oxopentenoate, 2-keto-4-pentenoate, oxopent-4-enoate, 2-keto-4-pentenoic acid, 2-ketopent-4-enoic acid

Citations: [He99]

Chemical Formula: C5H5O3

Molecular Weight: 113.09 Daltons

Monoisotopic Molecular Weight: 114.0316940589 Daltons

2-oxopent-4-enoate compound structure

SMILES: C=CCC(=O)C(=O)[O-]

InChI: InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8)/p-1

InChIKey: InChIKey=NOXRYJAWRSNUJD-UHFFFAOYSA-M

Unification Links: ChEBI:11641 , ChemSpider:7822120 , IAF1260:35454 , KEGG:C00596 , PubChem:9543147 , UMBBD-Compounds:c0102

Tautomers: (2Z)-2-hydroxypenta-2,4-dienoate , (3Z)-2-oxopent-3-enoate , (2E)-2-hydroxypenta-2,4-dienoate

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -36.70646 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

hypoglycin biosynthesis :
2-oxopent-4-enoate + an oxidized unknown electron acceptor → 2-oxopenta-3,4-dienoate + an reduced unknown electron acceptor

Reactions known to produce the compound:

2,2'-dihydroxybiphenyl degradation :
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O → 2-oxopent-4-enoate + salicylate + H+
2-hydroxy-6-oxo-6-(2,3-dihydroxyphenyl)-hexa-2,4-dienoate + H2O → 2,3-dihydroxybenzoate + 2-oxopent-4-enoate + H+

2,3-dihydroxybenzoate degradation , 2-amino-3-carboxymuconate semialdehyde degradation to 2-oxopentenoate , 2-aminophenol degradation , 2-nitrobenzoate degradation I , 3-chlorocatechol degradation III (meta pathway) , 4-amino-3-hydroxybenzoate degradation , catechol degradation to 2-oxopent-4-enoate II , orthanilate degradation , protocatechuate degradation III (para-cleavage pathway) :
(3E)-2-oxohex-3-enedioate + H+2-oxopent-4-enoate + CO2

2-hydroxybiphenyl degradation , biphenyl degradation :
2,6-dioxo-6-phenylhexa-3-enoate + H2O → 2-oxopent-4-enoate + benzoate + H+

2-nitrotoluene degradation , toluene degradation to 2-oxopent-4-enoate (via 4-methylcatechol) , toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol) , toluene degradation to 2-oxopent-4-enoate I (via o-cresol) :
cis,cis-2-hydroxy-6-oxohepta-2,4-dienoate + H2O → 2-oxopent-4-enoate + acetate + H+

2-propylphenol degradation :
2-hydroxy-6-oxo-nona-2,4-dienoate + H2O → butanoate + 2-oxopent-4-enoate + H+

catechol degradation to 2-oxopent-4-enoate I :
(2Z,4E)-2-hydroxy-6-oxohexa-2,4-dienoate + H2O → 2-oxopent-4-enoate + formate + H+

dibenzofuran degradation :
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O → 2-oxopent-4-enoate + salicylate + H+

hypoglycin biosynthesis :
5-hydroxy-2-oxopentanoate → 2-oxopent-4-enoate + H2O

Reactions known to both consume and produce the compound:

2-isopropylphenol degradation , p-cumate degradation to 2-oxopent-4-enoate :
2-hydroxy-6-oxo-7-methyl-octa-2,4-dienoate + H2O ↔ 2-oxopent-4-enoate + isobutanoate + H+

2-oxopentenoate degradation :
2-oxopent-4-enoate + H2O ↔ 4-hydroxy-2-oxopentanoate

3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation to 2-oxopent-4-enoate , cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate :
(2Z)-2-hydroxypenta-2,4-dienoate ↔ 2-oxopent-4-enoate

carbazole degradation , fluorene degradation I :
(2E)-2-hydroxypenta-2,4-dienoate ↔ 2-oxopent-4-enoate

Not in pathways:
2-oxopent-4-enoate ↔ (3Z)-2-oxopent-3-enoate

In Reactions of unknown directionality:

Not in pathways:
L-2-amino-4-chloropent-4-enoate + H2O = 2-oxopent-4-enoate + ammonium + chloride + H+

Enzymes inhibited by 2-oxopent-4-enoate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 4-oxalocrotonate tautomerase [Orii06]


References

He99: He Z, Spain JC (1999). "Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway)." Arch Microbiol 171(5);309-16. PMID: 10382261

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Orii06: Orii C, Takenaka S, Murakami S, Aoki K (2006). "Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols." Biosci Biotechnol Biochem 70(11);2653-61. PMID: 17090920


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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