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
Description
Structure
Thumb
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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Synonyms
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 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 ]