Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
twitter

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): -66.95647 Inferred 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

glycerol degradation to butanol :
butanoyl-CoA + acetoacetate ← butanoate + 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[periplasmic space]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 SRI International Pathway Tools version 19.0 on Fri Aug 28, 2015, biocyc12.