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Showing metabocard for 2-Methyl-3-oxopropanoic acid (HMDB0001172)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:30 UTC
HMDB IDHMDB0001172
Secondary Accession Numbers
  • HMDB01172
Metabolite Identification
Common Name2-Methyl-3-oxopropanoic acid
Description2-Methyl-3-oxopropanoic acid, also known as methylmalonate semialdehyde or 3-oxo-2-methylpropanoate, belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. The 2-methyl-3-oxo derivative of propanoic acid. 2-Methyl-3-oxopropanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methyl-3-oxopropanoic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1676999730
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

  Mrv0541 02231218582D          

  7  6  0  0  0  0            999 V2000
    0.1025   -0.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1025   -1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287   -0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112    1.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5336   -0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
M  END
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3D MOL for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

HMDB0001172
     RDKit          3D
2-Methyl-3-oxopropanoic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.2028   -0.6755   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2142    0.4522   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    1.1343    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    2.3384    1.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584   -0.0198   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    0.4524   -1.9751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802   -0.9453   -0.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -1.6591   -0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268   -0.6415    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212   -0.5561   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    1.1804   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4848    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588   -1.5451    0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  7 13  1  0
M  END
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3D SDF for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

  Mrv0541 02231218582D          

  7  6  0  0  0  0            999 V2000
    0.1025   -0.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1025   -1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287   -0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112    1.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5336   -0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001172

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.154549517532566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-oxopropanoic acid

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.05325275766666666

> <ALOGPS_LOGS>
0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.24521673888885

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.983843966096281

> <JCHEM_PKA_STRONGEST_BASIC>
-7.233962384073211

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.636900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylmalonate semialdehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

HMDB0001172
     RDKit          3D
2-Methyl-3-oxopropanoic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.2028   -0.6755   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2142    0.4522   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    1.1343    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0789    2.3384    1.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584   -0.0198   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    0.4524   -1.9751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802   -0.9453   -0.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -1.6591   -0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268   -0.6415    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212   -0.5561   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    1.1804   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4848    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588   -1.5451    0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  7 13  1  0
M  END
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PDB for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.191  -0.333   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.141   0.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.524   0.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.191  -1.871   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.480  -0.333   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.141   1.984   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.863  -0.333   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

COMPND    HMDB0001172
HETATM    1  C1  UNL     1       1.203  -0.676  -0.084  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.214   0.452  -0.289  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.096   1.134   1.010  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.079   2.338   1.154  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.058  -0.020  -0.867  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.420   0.452  -1.975  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.880  -0.945  -0.276  1.00  0.00           O  
HETATM    8  H1  UNL     1       0.765  -1.659  -0.314  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.527  -0.642   0.977  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.121  -0.556  -0.696  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.708   1.180  -0.962  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.345   0.485   1.839  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.659  -1.545   0.484  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    5   11
CONECT    3    4    4   12
CONECT    5    6    6    7
CONECT    7   13
END
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SMILES for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

CC(C=O)C(O)=O
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INCHI for HMDB0001172 (2-Methyl-3-oxopropanoic acid)

InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Methyl-3-oxopropanoateChEBI
3-oxo-2-MethylpropanoateChEBI
Methylmalonate semialdehydeChEBI
3-oxo-2-Methylpropanoic acidGenerator
Methylmalonic acid semialdehydeGenerator
CH3-Malonate-semialdehydeHMDB
Methylmalonate-semialdehydeHMDB
2-Methyl-3-oxo-propanoateHMDB
2-Methyl-3-oxopropanoic acidGenerator
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name2-methyl-3-oxopropanoic acid
Traditional Namemethylmalonate semialdehyde
CAS Registry Number6236-08-4
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 KeyVOKUMXABRRXHAR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct Parent1,3-dicarbonyl compounds
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022464
KNApSAcK IDNot Available
Chemspider ID290
KEGG Compound IDC00349
BioCyc IDNot Available
BiGG ID34698
Wikipedia Link2-Methyl-3-oxopropanoic acid
METLIN ID6053
PubChem Compound296
PDB IDNot Available
ChEBI ID16256
Food Biomarker OntologyNot Available
VMH ID2MOP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRobinson, 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 ReferencesNot Available

Enzymes

Enzyme Details
1. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Molecular weight:
57839.31
Reactions
2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD → Propionyl-CoA + Hydrogen carbonate + NADHdetails
Enzyme Details
2. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Enzyme Details
3. 4-aminobutyrate aminotransferase, mitochondrial
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
Reactions
(S)-beta-Aminoisobutyric acid + Oxoglutaric acid → 2-Methyl-3-oxopropanoic acid + Glutamic aciddetails
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Enzyme Details
5. Peroxisomal bifunctional enzyme
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Enzyme Details
6. 3-hydroxyisobutyrate dehydrogenase, mitochondrial
General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
Not Available
Gene Name:
HIBADH
Uniprot ID:
P31937
Molecular weight:
35328.515
Reactions
(S)-3-Hydroxyisobutyric acid + NAD → 2-Methyl-3-oxopropanoic acid + NADHdetails
Enzyme Details
7. Alanine--glyoxylate aminotransferase 2, mitochondrial
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
Reactions
(R)-beta-Aminoisobutyric acid + Pyruvic acid → 2-Methyl-3-oxopropanoic acid + L-Alaninedetails