Acetoacetate (BioCAD00000005759)
blood cellular cytoplasm cerebrospinal fluid (csf) feces saliva urine fibroblasts leukocyte liver neuron spleen
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
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.
DBLinks
- CAS Registry Number: 541-50-4
- PubChem CID: 96
- ChEBI: 13705
- HMDB: HMDB0000060
- LipidMaps: LMFA01060003
- KEGG: C00164
- BioCyc: 3-KETOBUTYRATE
- NCBI MeSH: acetoacetic acid
- Wikipedia: Acetoacetic_acid
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
- WishartLab ClassyFire: [Short-chain keto acids and derivatives] Short-chain keto acids and derivatives
- RefMet: [Oxo FA] Oxo FA
- LipidMaps: [Oxo fatty acids [FA0106]] Oxo fatty acids [FA0106]
- ChEBI: [CHEBI:15344] acetoacetic acid
- Coconut NaturalProduct: [Oxo fatty acids] Oxo fatty acids
| 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+ |
Taxonomy Source
- Citrullus lanatus [ncbi taxid: 3654]
- FOOD SAKE [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Pseudomonas putida [ncbi taxid: 303]