2-Oxobutanoate (BioCAD00000002765)
Metabolite Card
Formula: C4H6O3 (102.0317)
SMILES: CCC(=O)C(O)=O
Synonyms [en]
2-oxobutyric acid; 2-oxobutanoate; 2-ketobutyric acid; alpha-ketobutyric acid; 3-methyl pyruvic acid; 2-oxo-butanoic acid
Last reviewed on 2024-06-28.
Cite this Page
2-Oxobutanoate. 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: BioCAD00000002765). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. It is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. More specifically, 2-ketobutyric acid is a product of the lysis of cystathionine.
DBLinks
- CAS Registry Number: 600-18-0
- PubChem CID: 58
- ChEBI: 16763
- HMDB: HMDB0000005
- LipidMaps: LMFA01060002
- KEGG: C00109
- BioCyc: 2-OXOBUTANOATE
- NCBI MeSH: alpha-ketobutyric acid
- Wikipedia: Alpha-Ketobutyric_acid
Other DBLinks
- CAS Registry Number: 600-18-0
- PubChem: 3409
- PubChem: 58
- ChEBI: ChEBI:16763
- ChEBI: ChEBI:30831
- HMDB: HMDB0000005
- LipidMaps: LMFA01060002
- KEGG: C00109
- BioCyc: 2-OXOBUTANOATE
- NCBI MeSH: alpha-ketobutyric acid
- Wikipedia: %CE%91-Ketobutyric_acid
- Wikipedia: Alpha-Ketobutyric_acid
- DrugBank: DB04553
- RefMet: RM0153036
- MoNA: BAF_UVA_POS000446
- MoNA: BAF_UVA_POS001568
- MoNA: EMBL_MCF_2_0_HRMS_Library000279
- MoNA: FiehnLib000470
- MoNA: FiehnLib000471
- MoNA: GLS00024
- MoNA: GLS00025
- MoNA: HMDB0000005_c_ms_936
- MoNA: HMDB0000005_c_ms_937
- MoNA: HMDB0000005_c_ms_943
- MoNA: HMDB0000005_ms_ms_7
- MoNA: HMDB0000005_ms_ms_8
- MoNA: HMDB0000005_ms_ms_9
- MoNA: MoNA016821
- MoNA: MoNA_0009285
- MoNA: OUF00039
- MoNA: OUF00040
- MoNA: PR100863
- MoNA: PS062301
- MoNA: PS062302
- MoNA: PS101801
- MoNA: PS101807
- Metlin: METLIN_481
- Coconut NaturalProduct: CNP0283357.0
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:30831] 2-oxobutanoic acid
- Coconut NaturalProduct: [Oxo fatty acids] Oxo fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R00654 | 4.4.1.11 | L-methionine methanethiol-lyase (deaminating;2-oxobutanoate-forming) |
| KEGG:R00993 | 1.2.3.- | 2-oxobutanoate:oxygen 2-oxidoreductase (phosphorylating) |
| KEGG:R00994 | 1.1.1.85 | (2R,3S)-3-methylmalate:NAD+ oxidoreductase |
| KEGG:R00995 | 4.1.1.112 | methyloxaloacetate carboxy-lyase (2-oxobutanoate-forming) |
| KEGG:R00996 | 4.3.1.19 | L-threonine ammonia-lyase (2-oxobutanoate-forming) |
| KEGG:R00997 | 3.5.99.7 | 1-aminocyclopropane-1-carboxylate aminohydrolase (isomerizing); |
| KEGG:R00998 | 2.3.3.6 | acetyl-CoA:2-oxobutanoate C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming); |
| KEGG:R00999 | 2.5.1.48 | O-succinyl-L-homoserine succinate-lyase (deaminating; 2-oxobutanoate-forming) |
| KEGG:R01000 | 1.1.1.27 | 2-hydroxybutyrate:NAD+ oxidoreductase |
| KEGG:R01001 | 4.4.1.1 | L-cystathionine cysteine-lyase (deaminating; 2-oxobutanoate-forming) |
| KEGG:R01199 | 1.2.7.1 | 2-oxobutanoate:ferredoxin 2-oxidoreductase (CoA-propanoylating) |
| KEGG:R01283 | 4.4.1.2 | L-homocysteine hydrogen-sulfide-lyase (deaminating; 2-oxobutanoate-forming) |
| KEGG:R04673 | 2.2.1.6 | (S)-2-aceto-2-hydroxybutanoate pyruvate-lyase (carboxylating) |
| KEGG:R04770 | 4.4.1.1 | selenomethionine methanethiol-lyase (deaminating) |
| KEGG:R04930 | 4.4.1.1 | selenocystathionine lysteine-lyase (deaminating) |
| KEGG:R05840 | C00266 + C00109 + C01401<=>C00314 | |
| KEGG:R06987 | 2.3.1.54 | propanoyl-CoA:formate C-propanoyltransferase |
| KEGG:R08637 | 2-aminobut-2-enoate aminohydrolase (spontaneous) | |
| KEGG:R08648 | 2.2.1.6 | pyruvate:2-oxobutanoate acetaldehydetransferase (decarboxylating) |
| KEGG:R10991 | 2.6.1.42 | 2-aminobutanoate:2-oxoglutarate aminotransferase |
Taxonomy Source
- Citrullus lanatus [ncbi taxid: 3654]
- Escherichia coli K12 [ncbi taxid: ]
- FOOD SAKE [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:CALBI_THREOCAT-PWY | threonine degradation |
| BioCyc:CALBI_ILEUSYN-PWY | isoleucine biosynthesis |
| BioCyc:CALBI_PWY-801 | cysteine and homocysteine interconversion |
| BioCyc:CALBI_BRANCHED-CHAIN-AA-SYN-PWY | superpathway of leucine, valine, and isoleucine biosynthesis |
| PathBank:SMP0000838 | Isoleucine Biosynthesis |
| PathBank:SMP0000957 | Propanoate Metabolism |
| Plant Reactome:R-OAU-2744345 | Metabolism and regulation |
| Plant Reactome:R-OAU-2744343 | Amino acid metabolism |
| Plant Reactome:R-TAE-1119460 | Isoleucine biosynthesis from threonine |
| Plant Reactome:R-FVE-5655122 | Amino acid biosynthesis |
| Plant Reactome:R-MES-2744345 | Metabolism and regulation |
| Plant Reactome:R-MES-2744343 | Amino acid metabolism |
| Plant Reactome:R-TDI-2744345 | Metabolism and regulation |
| Plant Reactome:R-TDI-2744343 | Amino acid metabolism |
| Plant Reactome:R-DRO-2744345 | Metabolism and regulation |
| Plant Reactome:R-DRO-5655122 | Amino acid biosynthesis |
| Plant Reactome:R-DRO-1119460 | Isoleucine biosynthesis from threonine |
| Plant Reactome:R-OMI-5655122 | Amino acid biosynthesis |
| Plant Reactome:R-OMI-1119460 | Isoleucine biosynthesis from threonine |
| Plant Reactome:R-PTI-2744345 | Metabolism and regulation |