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MetaCyc Compound: acetoacetate

Synonyms: 3-ketobutyrate, 3-oxobutanate, oxobutyrate, acetoacetic acid, 3-oxobutyric acid, 3-oxobutanoic acid, diacetic acid, β-ketobutyric acid

Chemical Formula: C4H5O3

Molecular Weight: 101.08 Daltons

Monoisotopic Molecular Weight: 102.0316940589 Daltons

acetoacetate compound structure

SMILES: CC(=O)CC([O-])=O

InChI: InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1

InChIKey: InChIKey=WDJHALXBUFZDSR-UHFFFAOYSA-M

Unification Links: CAS:541-50-4, ChEBI:13705, ChemSpider:5341896, HMDB:HMDB00060, IAF1260:1485291, KEGG:C00164, MetaboLights:MTBLC13705, PubChem:6971017, UMBBD-Compounds:c0069

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -66.95647Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

acetone degradation I (to methylglyoxal) , acetone degradation III (to propane-1,2-diol) , isopropanol biosynthesis , ketogenesis , pyruvate fermentation to acetone :
acetoacetate + H+ → acetone + CO2

Not in pathways:
acetoacetate + ATP + coenzyme A → acetoacetyl-CoA + AMP + diphosphate

Reactions known to produce the compound:

acetone degradation II (to acetoacetate) :
acetone + CO2 + ATP + 2 H2O → acetoacetate + AMP + 2 phosphate + 3 H+

isopropanol biosynthesis :
acetoacetyl-CoA + H2O → acetoacetate + coenzyme A + H+

ketogenesis , L-leucine degradation I , mevalonate degradation :
(S)-3-hydroxy-3-methylglutaryl-CoA → acetoacetate + acetyl-CoA

L-tyrosine degradation I :
4-fumaryl-acetoacetate + H2O → fumarate + acetoacetate + H+

propylene degradation :
acetoacetate + coenzyme M + NADP+ ← 2-oxopropyl-CoM + CO2 + NADPH

Reactions known to both consume and produce the compound:

acetoacetate degradation (to acetyl CoA) :
acetyl-CoA + acetoacetate ↔ acetate + acetoacetyl-CoA

ketogenesis :
(R)-3-hydroxybutanoate + NAD+acetoacetate + NADH + H+

ketolysis :
(R)-3-hydroxybutanoate + NAD+acetoacetate + NADH + H+
succinyl-CoA + acetoacetate ↔ succinate + acetoacetyl-CoA

L-lysine fermentation to acetate and butanoate :
(S)-5-amino-3-oxohexanoate + acetyl-CoA ↔ (S)-3-aminobutanoyl-CoA + acetoacetate
butanoyl-CoA + acetoacetate ← butanoate + acetoacetyl-CoA

pyruvate fermentation to acetone :
acetyl-CoA + acetoacetate ↔ acetate + acetoacetyl-CoA
butanoyl-CoA + acetoacetate ← butanoate + acetoacetyl-CoA

TCA cycle VIII (helicobacter) :
succinyl-CoA + acetoacetate ↔ succinate + acetoacetyl-CoA

In Reactions of unknown directionality:

Not in pathways:
(S)-3-hydroxybutanoate + 2-oxoglutarate = (R)-2-hydroxyglutarate + acetoacetate
2-oxo-2-[4,5,7,10-tetrahydroxy-3-(3-oxobutanoyl)anthracen-2-yl]acetyl-[PKS-acp] + acetoacetate = 1-[4,5,7,10-tetrahydroxy-3-(3-oxobutanoyl)anthracen-2-yl]pentane-1,2,4-trione + polyketide synthase + CO2 + H+

In Transport reactions:
acetoacetate[periplasm]acetoacetate[cytosol]

Enzymes inhibited by acetoacetate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: acetyl-coA synthetase [Luong00], hydroxymethylglutaryl-CoA reductase [Gill85], succinate dehydrogenase [Burke82]

This compound has been characterized as an alternative substrate of the following enzymes: succinyl-CoA:acetate CoA-transferase


References

Burke82: Burke JJ, Siedow JN, Moreland DE (1982). "Succinate Dehydrogenase : A Partial Purification from Mung Bean Hypocotyls and Soybean Cotyledons." Plant Physiol 70(6);1577-1581. PMID: 16662722

Gill85: Gill JF, Beach MJ, Rodwell VW (1985). "Mevalonate utilization in Pseudomonas sp. M. Purification and characterization of an inducible 3-hydroxy-3-methylglutaryl coenzyme A reductase." J Biol Chem 260(16);9393-8. PMID: 4019479

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

Luong00: Luong A, Hannah VC, Brown MS, Goldstein JL (2000). "Molecular characterization of human acetyl-CoA synthetase, an enzyme regulated by sterol regulatory element-binding proteins." J Biol Chem 275(34);26458-66. PMID: 10843999


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Wed Feb 10, 2016, biocyc13.