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Showing NP-Card for 3-Methyl-2-oxovaleric acid (NP0000199)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:18:42 UTC
NP-MRD IDNP0000199
Natural Product DOIhttps://doi.org/10.57994/1481
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyl-2-oxovaleric acid
Description3-Methyl-2-oxovaleric acid is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 3-methyl-2-oxovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465 ). 3-Methyl-2-oxovaleric acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000199 (3-Methyl-2-oxovaleric acid)


  Mrv1652309042000012D          

  9  8  0  0  0  0            999 V2000
10026.389310026.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.106610026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.820210026.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10028.535810026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.106610027.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.674710026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.960110026.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.674710027.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.389310025.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0000199 (3-Methyl-2-oxovaleric acid)

NP0000199
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.2795    0.1330    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    0.3033    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1289    0.5865   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -0.6133   -1.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.7167   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523    1.8114   -0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -0.3635    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -1.4311    0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536   -0.2707    0.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    0.7012    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416   -0.9376    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.4501    1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.6576    1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861    1.0829    1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978    1.4780   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -0.4528   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -1.5432   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -0.5593   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.4341   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0000199 (3-Methyl-2-oxovaleric acid)


  Mrv1652309042000012D          

  9  8  0  0  0  0            999 V2000
10026.389310026.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.106610026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.820210026.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10028.535810026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.106610027.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.674710026.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.960110026.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.674710027.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.389310025.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

> <INCHI_KEY>
JVQYSWDUAOAHFM-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.092337840641136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.7539647436666668

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5188639238905273

> <JCHEM_PKA_STRONGEST_BASIC>
-9.724255725220358

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
31.792099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-2-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000199 (3-Methyl-2-oxovaleric acid)

NP0000199
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.2795    0.1330    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    0.3033    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1289    0.5865   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -0.6133   -1.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.7167   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523    1.8114   -0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -0.3635    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238   -1.4311    0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536   -0.2707    0.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    0.7012    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416   -0.9376    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.4501    1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.6576    1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861    1.0829    1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978    1.4780   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -0.4528   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -1.5432   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -0.5593   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.4341   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
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PDB for NP0000199 (3-Methyl-2-oxovaleric acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8715.9278716.202   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8717.2668716.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8718.5988716.202   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8719.9338716.971   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8717.2668718.511   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8714.5938716.971   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8713.2598716.202   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8714.5938718.511   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8715.9278714.662   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000199 (3-Methyl-2-oxovaleric acid)

COMPND    NP0000199
HETATM    1  C1  UNL     1      -2.280   0.133   0.927  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.787   0.303   1.186  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.129   0.586  -0.139  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.412  -0.613  -1.039  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.336   0.717  -0.049  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.852   1.811  -0.404  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.179  -0.363   0.427  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.624  -1.431   0.767  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.554  -0.271   0.523  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.590   0.701   0.034  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.542  -0.938   0.747  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.885   0.450   1.812  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.417  -0.658   1.595  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.586   1.083   1.941  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.598   1.478  -0.561  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.448  -0.453  -1.425  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.359  -1.543  -0.468  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.314  -0.559  -1.862  1.00  0.00           H  
HETATM   19  H10 UNL     1       4.173  -0.434  -0.282  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    5   15
CONECT    4   16   17   18
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for NP0000199 (3-Methyl-2-oxovaleric acid)

CCC(C)C(=O)C(O)=O
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INCHI for NP0000199 (3-Methyl-2-oxovaleric acid)

InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-oxo-3-Methyl-N-valeric acidChEBI
2-oxo-3-Methylpentanoic acidChEBI
2-oxo-3-MethylvalerateChEBI
2-oxo-3-Methylvaleric acidChEBI
2-OxoisoleucineChEBI
2-Oxokolavenic acidChEBI
3-Ethyl-3-methylpyruvic acidChEBI
3-Methyl-2-oxopentanoic acidChEBI
alpha-Keto-beta-methyl-N-valeric acidChEBI
alpha-Keto-beta-methylvaleric acidChEBI
alpha-oxo-beta-Methyl-N-valeric acidChEBI
alpha-oxo-beta-Methylvaleric acidChEBI
KetoisoleucineChEBI
2-oxo-3-Methyl-N-valerateGenerator
2-oxo-3-MethylpentanoateGenerator
2-OxokolavenateGenerator
3-Ethyl-3-methylpyruvateGenerator
3-Methyl-2-oxopentanoateGenerator
a-Keto-b-methyl-N-valerateGenerator
a-Keto-b-methyl-N-valeric acidGenerator
alpha-Keto-beta-methyl-N-valerateGenerator
Α-keto-β-methyl-N-valerateGenerator
Α-keto-β-methyl-N-valeric acidGenerator
a-Keto-b-methylvalerateGenerator
a-Keto-b-methylvaleric acidGenerator
alpha-Keto-beta-methylvalerateGenerator
Α-keto-β-methylvalerateGenerator
Α-keto-β-methylvaleric acidGenerator
a-oxo-b-Methyl-N-valerateGenerator
a-oxo-b-Methyl-N-valeric acidGenerator
alpha-oxo-beta-Methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valeric acidGenerator
a-oxo-b-MethylvalerateGenerator
a-oxo-b-Methylvaleric acidGenerator
alpha-oxo-beta-MethylvalerateGenerator
Α-oxo-β-methylvalerateGenerator
Α-oxo-β-methylvaleric acidGenerator
3-Methyl-2-oxovalerateGenerator
(3R)-3-Methyl-2-oxopentanoateHMDB
(3R)-3-Methyl-2-oxopentanoic acidHMDB
(R)-3-Methyl-2-oxopentanoateHMDB
(R)-3-Methyl-2-oxopentanoic acidHMDB
(S)-3-Methyl-2-oxopentanoateHMDB
(S)-3-Methyl-2-oxopentanoic acidHMDB
2-keto-3-MethylvalerateHMDB
2-keto-3-Methylvaleric acidHMDB, MeSH
3-Methyl-2-oxo-pentanoateHMDB
3-Methyl-2-oxo-pentanoic acidHMDB
3-Methyl-2-oxo-valerateHMDB
3-Methyl-2-oxo-valeric acidHMDB
3-Methyl-2-oxovalericHMDB
2-keto MethylvalerateMeSH, HMDB
KMVAMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, calcium salt, (S)-isomerMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, monosodium salt, (S)-isomerMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, (S)-isomerMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, calcium saltMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, sodium salt, (+-)-isomerMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, (+-)-isomerMeSH, HMDB
alpha-keto-beta-Methylvaleric acid, sodium saltMeSH, HMDB
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
IUPAC Name3-methyl-2-oxopentanoic acid
Traditional Name3-methyl-2-oxopentanoic acid
CAS Registry Number1460-34-0
SMILES
CCC(C)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyJVQYSWDUAOAHFM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-12-21View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-12-21View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-12-21View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-12-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-12-21View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point41.00 to 42.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point233.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility915.5 mg/mLNot Available
LogP0.133 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility9.86 g/LALOGPS
logP1ALOGPS
logP1.75ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.79 m³·mol⁻¹ChemAxon
Polarizability13.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021448
KNApSAcK IDC00052148
Chemspider ID46
KEGG Compound IDC03465
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID35932
Good Scents IDrw1465111
References
General References
  1. Wendel U, Even G, Langenbeck U, Schadewaldt P, Hummel W: Determination of (S)- and (R)-2-oxo-3-methylvaleric acid in plasma of patients with maple syrup urine disease. Clin Chim Acta. 1992 Jun 15;208(1-2):85-91. [PubMed:1638756 ]
  2. Przyrembel H, Bremer HJ, Duran M, Bruinvis L, Ketting D, Wadman SK, Baumgartner R, Irle U, Bachmann C: Propionyl-CoA carboxylase deficiency with overflow of metabolites of isoleucine catabolism at all levels. Eur J Pediatr. 1979 Jan 18;130(1):1-14. [PubMed:759179 ]