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Human Metabolome Database Version 3.5

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Showing metabocard for 2-Methyl-3-oxopropanoic acid (HMDB01172)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:01 -0700
HMDB ID HMDB01172
Secondary Accession Numbers None
Metabolite Identification
Common Name 2-Methyl-3-oxopropanoic acid
Description 2-Methyl-3-oxopropanoic acid is an intermediate in the metabolism of Propanoate. It is a substrate for 3-hydroxyisobutyrate dehydrogenase (mitochondrial), Alanine--glyoxylate aminotransferase 2 (mitochondrial) and Methylmalonate-semialdehyde dehydrogenase (mitochondrial).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Methyl-3-oxopropanoate
  2. 2-Methyl-3-oxopropanoic acid
  3. 3-Oxo-2-methylpropanoate
  4. 3-Oxo-2-methylpropanoic acid
  5. Ch3-malonate-semialdehyde
  6. Methylmalonate semialdehyde
  7. Methylmalonate-semialdehyde
Chemical Formula C4H6O3
Average Molecular Weight 102.0886
Monoisotopic Molecular Weight 102.031694058
IUPAC Name 2-methyl-3-oxopropanoic acid
Traditional IUPAC Name 2-methyl-3-oxopropanoic acid
CAS Registry Number 6236-08-4
SMILES CC(C=O)C(O)=O
InChI Identifier InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)
InChI Key VOKUMXABRRXHAR-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Carboxylic Acid Derivatives
Other Descriptors
  • 2-methyl-3-oxopropanoic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Oxo fatty acids(Lipidmaps)
  • semialdehyde(ChEBI)
Substituents
  • Aldehyde
Direct Parent Carboxylic Acids
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Inositol metabolism
  • Component of Propanoate metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 266 g/L ALOGPS
LogP -0.00 ALOGPS
LogP 0.053 ChemAxon
LogS 0.42 ALOGPS
pKa (strongest acidic) 3.98 ChemAxon
pKa (strongest basic) -7.2 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 22.64 ChemAxon
Polarizability 9.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022464
KNApSAcK ID Not Available
Chemspider ID 290 Link_out
KEGG Compound ID C00349 Link_out
BioCyc ID CH3-MALONATE-S-ALD Link_out
BiGG ID 34698 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01172 Link_out
Metagene Link HMDB01172 Link_out
METLIN ID 6053 Link_out
PubChem Compound 296 Link_out
PDB ID Not Available
ChEBI ID 16256 Link_out
References
Synthesis Reference Robinson, Wm. G.; Coon, Minor J. Purification and properties of b-hydroxyisobutyric dehydrogenase. Journal of Biological Chemistry (1957), 225 511-21.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
Reactions:
2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD unknown Propionyl-CoA + Carbonic acid + NADH details
Gene Name: ALDH6A1
Uniprot ID: Q02252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde oxidase
Reactions: Not Available
Gene Name: AOX1
Uniprot ID: Q06278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 4-aminobutyrate aminotransferase, mitochondrial
Reactions:
(S)-b-aminoisobutyric acid + Oxoglutaric acid unknown 2-Methyl-3-oxopropanoic acid + L-Glutamic acid details
Gene Name: ABAT
Uniprot ID: P80404 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal bifunctional enzyme
Reactions: Not Available
Gene Name: EHHADH
Uniprot ID: Q08426 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-hydroxyisobutyrate dehydrogenase, mitochondrial
Reactions:
(S)-3-Hydroxyisobutyric acid + NAD unknown 2-Methyl-3-oxopropanoic acid + NADH details
Gene Name: HIBADH
Uniprot ID: P31937 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alanine--glyoxylate aminotransferase 2, mitochondrial
Reactions:
(R)-b-aminoisobutyric acid + Pyruvic acid unknown 2-Methyl-3-oxopropanoic acid + L-Alanine details
Gene Name: AGXT2
Uniprot ID: Q9BYV1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA