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Showing metabocard for 2-Oxovaleric acid (HMDB0001865)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 10:36:27 UTC
Update Date2023-02-21 17:15:52 UTC
HMDB IDHMDB0001865
Secondary Accession Numbers
  • HMDB01865
Metabolite Identification
Common Name2-Oxovaleric acid
Description2-Oxovaleric acid, also known as 2-oxovalerate or a-ketovalerate, 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-Oxovaleric acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and herbs and spices. This could make 2-oxovaleric acid a potential biomarker for the consumption of these foods. 2-Oxovaleric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2-Oxovaleric acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001865 (2-Oxovaleric acid)

  Mrv0541 02231219142D          

  8  7  0  0  0  0            999 V2000
   17.9009   -4.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3298   -4.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6154   -2.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4720   -4.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1866   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7576   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9009   -4.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6154   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for HMDB0001865 (2-Oxovaleric acid)

HMDB0001865
     RDKit          3D
2-Oxovaleric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.5309   -0.3463    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2475    0.0895   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -0.2673    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1690    0.2114   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498    0.8089   -1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    0.0133    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561   -0.5871    1.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.4393   -0.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7046    0.0476    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.0148   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -1.4467    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.3677   -1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2849    1.1955   -0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0134    0.2008    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -1.3599    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531    1.3536   -0.7808 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
  4  5  2  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0001865 (2-Oxovaleric acid)

  Mrv0541 02231219142D          

  8  7  0  0  0  0            999 V2000
   17.9009   -4.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3298   -4.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6154   -2.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4720   -4.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1866   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7576   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9009   -4.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6154   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001865

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)

> <INCHI_KEY>
KDVFRMMRZOCFLS-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
11.19453268029834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopentanoic acid

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
1.210978465333333

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3807740318508506

> <JCHEM_PKA_STRONGEST_BASIC>
-9.65651050049784

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
27.217599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001865 (2-Oxovaleric acid)

HMDB0001865
     RDKit          3D
2-Oxovaleric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.5309   -0.3463    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2475    0.0895   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -0.2673    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1690    0.2114   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498    0.8089   -1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    0.0133    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561   -0.5871    1.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.4393   -0.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7046    0.0476    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.0148   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -1.4467    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.3677   -1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2849    1.1955   -0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0134    0.2008    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -1.3599    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531    1.3536   -0.7808 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
  4  5  2  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0001865 (2-Oxovaleric 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  O   UNK     0      33.415  -9.291   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.082  -7.752   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.749  -5.441   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      30.748  -7.752   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.082  -6.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.414  -6.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.415  -7.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.749  -6.981   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4                                                            
CONECT    7    1    5    8                                                  
CONECT    8    2    3    7                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0001865 (2-Oxovaleric acid)

COMPND    HMDB0001865
HETATM    1  C1  UNL     1       2.531  -0.346   0.271  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.248   0.089  -0.370  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.030  -0.267   0.413  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.169   0.211  -0.314  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.050   0.809  -1.407  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.522   0.013   0.197  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.656  -0.587   1.297  1.00  0.00           O  
HETATM    8  O3  UNL     1      -3.652   0.439  -0.443  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.705   0.048   1.271  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.361   0.015  -0.397  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.626  -1.447   0.289  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.205  -0.368  -1.376  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.285   1.196  -0.466  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.013   0.201   1.416  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.101  -1.360   0.554  1.00  0.00           H  
HETATM   16  H8  UNL     1      -3.853   1.354  -0.781  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    5    6
CONECT    6    7    7    8
CONECT    8   16
END
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SMILES for HMDB0001865 (2-Oxovaleric acid)

CCCC(=O)C(O)=O
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INCHI for HMDB0001865 (2-Oxovaleric acid)

InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name2-oxopentanoic acid
Traditional Nameα-oxopentanoic acid
CAS Registry Number1821-02-9
SMILES
CCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyKDVFRMMRZOCFLS-UHFFFAOYSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point6.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.35Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.9 +/- 2.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0-300 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified0.45 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003366
KNApSAcK IDC00055637
Chemspider ID67142
KEGG Compound IDC06255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74563
PDB IDNot Available
ChEBI ID33033
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLieberman, Irving; Barker, H. A. b-Keto acid formation and decomposition by preparations of Clostridium kluyveri. Journal of Bacteriology (1954), 68 329-33.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
  2. Fu X, Kimura M, Iga M, Yamaguchi S: Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):87-94. [PubMed:11482739 ]
  3. Wang ZJ, Zaitsu K, Ohkura Y: High-performance liquid chromatographic determination of alpha-keto acids in human serum and urine using 1,2-diamino-4,5-methylenedioxybenzene as a precolumn fluorescence derivatization reagent. J Chromatogr. 1988 Sep 9;430(2):223-31. [PubMed:3235498 ]