Metabolite Card

Formula: C4H6O3 (102.0317)
SMILES: CC(=O)CC(O)=O

Synonyms [en]

acetoacetic acid; acetoacetate; 3-oxobutanoic acid; beta-ketobutyric acid; 3-ketobutanoic acid; 3-oxobutyric acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Acetoacetate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000005759). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Acetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 4387-93-3
  • CAS Registry Number: 541-50-4
  • CAS Registry Number: 578486
  • PubChem: 96
  • ChEBI: ChEBI:13705
  • ChEBI: ChEBI:15344
  • HMDB: HMDB0000060
  • HMDB: HMDB00060
  • LipidMaps: LMFA01060003
  • KEGG: C00164
  • BioCyc: 3-KETOBUTYRATE
  • NCBI MeSH: acetoacetic acid
  • Wikipedia: Acetoacetic_acid
  • DrugBank: DB01762
  • RefMet: RM0153222
  • MoNA: BAF_UVA_POS000503
  • MoNA: CCMSLIB00000578088
  • MoNA: EMBL_MCF_2_0_HRMS_Library000356
  • MoNA: HMDB0000060_c_ms_916
  • MoNA: HMDB0000060_c_ms_920
  • MoNA: HMDB0000060_c_ms_962
  • MoNA: HMDB0000060_c_ms_976
  • MoNA: HMDB0000060_ms_ms_96
  • MoNA: HMDB0000060_ms_ms_97
  • MoNA: HMDB0000060_ms_ms_98
  • MoNA: MoNA034844
  • MoNA: MoNA034848
  • MoNA: MoNA034851
  • MoNA: MoNA038344
  • MoNA: OUF00092
  • MoNA: PS008201
  • Metlin: METLIN_276
  • Coconut NaturalProduct: CNP0286292.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00410 2.8.3.5 succinyl-CoA:acetoacetate CoA-transferase
KEGG:R01357 6.2.1.16 acetoacetate:CoA ligase (AMP-forming)
KEGG:R01358 3.1.2.11 acetoacetyl-CoA hydrolase
KEGG:R01359 2.8.3.8 acetoacetyl-CoA:acetate CoA-transferase
KEGG:R01360 4.1.3.4 (S)-3-hydroxy-3-methylglutaryl-CoA acetoacetate-lyase (acetyl-CoA-forming)
KEGG:R01361 1.1.1.30 (R)-3-hydroxybutanoate:NAD+ oxidoreductase
KEGG:R01364 3.7.1.2 4-fumarylacetoacetate fumarylhydrolase
KEGG:R01365 2.8.3.9 butanoyl-CoA:acetoacetate CoA-transferase
KEGG:R01366 4.1.1.4 acetoacetate carboxy-lyase (acetone-forming)
KEGG:R01367 4.2.1.27 acetoacetate hydro-lyase (3-butynoate-forming)
KEGG:R03225 1.1.99.24 (S)-3-hydroxybutanoate:2-oxoglutarate oxidoreductase
KEGG:R05713 1.8.1.5 2-mercaptoethanesulfonate,acetoacetate:NADP+ oxidoreductase (decarboxylating)
KEGG:R05735 6.4.1.6 acetone:carbon-dioxide ligase (AMP-forming)
KEGG:R10564 2.3.1.247 (5S)-5-amino-3-oxohexanoate:acetyl-CoA ethylamine transferase
KEGG:R13359 2.3.1.317 3-dehydrocarnitine:acetyl-CoA trimethylamine transferase
KEGG:R13360 2.3.1.318 3-oxoadipate:acetyl-CoA acetyltransferase
KEGG:R13361 2.3.1.319 3,5-dioxohexanoate:acetyl-CoA acetone transferase
BioCyc:ACETOACETYL-COA-TRANSFER-RXN 2.8.3.9 3-KETOBUTYRATE + ACETYL-COA<=>ACETOACETYL-COA + ACET
BioCyc:TRANS-RXN0-281 3-KETOBUTYRATE --> 3-KETOBUTYRATE
Rhea:RHEA:10245 3.7.1.2 4-fumarylacetoacetate + H2O => acetoacetate + fumarate + H+
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Organism Source

Taxonomy Source

  1. Citrullus lanatus [ncbi taxid: 3654]
  2. FOOD SAKE [ncbi taxid: ]
  3. Homo sapiens [ncbi taxid: 9606]
  4. Pseudomonas putida [ncbi taxid: 303]

Pathway Synthetic

pathway id name
PathBank:SMP0002102 Acetate Metabolism
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-2744343 Amino acid metabolism
Plant Reactome:R-FVE-1119506 tyrosine degradation I
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744343 Amino acid metabolism
Plant Reactome:R-MES-5655124 Amino acid catabolism
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744343 Amino acid metabolism
Plant Reactome:R-TDI-1119506 tyrosine degradation I
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-OGU-1119506 tyrosine degradation I
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-2744343 Amino acid metabolism
Plant Reactome:R-PTI-5655124 Amino acid catabolism
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744343 Amino acid metabolism
Plant Reactome:R-GMA-1119506 tyrosine degradation I
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PDA-2744343 Amino acid metabolism
View All Pathways