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Showing NP-Card for 2-Methyl-3-ketovaleric acid (NP0000265)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:08 UTC
NP-MRD IDNP0000265
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Methyl-3-ketovaleric acid
Description2-Methyl-3-ketovaleric acid is a metabolite of beta-leucine in the beta-keto pathway of leucine metabolism. 2-Methyl-3-ketovaleric acid is a known pathological metabolite and associated with propionic acidemia, especially during periods of ketoacidosis; a severe deficiency of propionyl-CoA carboxylase in cultured fibroblasts has been detected in some neonatal cases. (PMID 7389125 , 6820422 , 7119896 , 7430116 , 3356699 ). 2-Methyl-3-ketovaleric acid induces a strong activity of inosine-5'-monophosphate dehydrogenase (IMPDH; the rate-limiting enzyme in GTP synthesis), mimicking glucose. (PMID: 11145582 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000265 (2-Methyl-3-ketovaleric acid)

2-Methyl-3-ketovaleric acid.mol
  Mrv1652305261923542D          

  9  8  0  0  0  0            999 V2000
    1.0715    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -0.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    1.0302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  3  8  2  0  0  0  0
  2  9  1  0  0  0  0
M  END
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3D MOL for NP0000265 (2-Methyl-3-ketovaleric acid)

HMDB0000408
     RDKit          3D
2-Methyl-3-ketovaleric acid
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.7888   -0.3853   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602   -0.5321    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    0.4222    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    1.2137   -0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.3813    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -1.0101    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122    1.4027    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3412    2.2960    0.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912    1.3775   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5589   -0.8315    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599    0.7055   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -0.8408   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927   -1.5709    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360   -0.2549    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605    0.5463    1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.9835    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -1.6434    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1890   -1.4320   -0.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445    1.1392   -1.5385 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
  3  5  1  0
  5  6  1  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
  5 15  1  0
  6 16  1  0
  6 17  1  0
  6 18  1  0
  9 19  1  0
M  END
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3D SDF for NP0000265 (2-Methyl-3-ketovaleric acid)

2-Methyl-3-ketovaleric acid.mol
  Mrv1652305261923542D          

  9  8  0  0  0  0            999 V2000
    1.0715    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -0.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    1.0302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  3  8  2  0  0  0  0
  2  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000265

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
QTLYPQZWYOHATR-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.945280405536801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
1.242030379666667

> <ALOGPS_LOGS>
-0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.628063934499679

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.322292270091543

> <JCHEM_PKA_STRONGEST_BASIC>
-7.592053777420283

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
31.740300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.06e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000265 (2-Methyl-3-ketovaleric acid)

HMDB0000408
     RDKit          3D
2-Methyl-3-ketovaleric acid
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.7888   -0.3853   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602   -0.5321    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    0.4222    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    1.2137   -0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.3813    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -1.0101    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122    1.4027    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3412    2.2960    0.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912    1.3775   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5589   -0.8315    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599    0.7055   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956   -0.8408   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927   -1.5709    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360   -0.2549    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605    0.5463    1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.9835    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -1.6434    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1890   -1.4320   -0.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445    1.1392   -1.5385 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
  3  5  1  0
  5  6  1  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
  5 15  1  0
  6 16  1  0
  6 17  1  0
  6 18  1  0
  9 19  1  0
M  END
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PDB for NP0000265 (2-Methyl-3-ketovaleric acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Methyl-3-ketovaleric acid.mol                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.000   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   0.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.000  -0.388   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.335   0.380   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.999   1.926   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.335  -0.383   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.669   1.923   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.669  -1.926   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    3                                                            
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000265 (2-Methyl-3-ketovaleric acid)

COMPND    HMDB0000408
HETATM    1  C1  UNL     1       2.789  -0.385  -0.141  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.460  -0.532   0.568  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.448   0.422   0.033  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.683   1.214  -0.864  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.908   0.381   0.646  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.511  -1.010   0.454  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.812   1.403   0.082  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.341   2.296   0.778  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.091   1.377  -1.269  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.559  -0.832   0.527  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.960   0.706  -0.275  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.796  -0.841  -1.144  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.093  -1.571   0.571  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.636  -0.255   1.630  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.760   0.546   1.743  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.610  -0.983   0.520  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.155  -1.643   1.293  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.189  -1.432  -0.541  1.00  0.00           H  
HETATM   19  H10 UNL     1      -3.044   1.139  -1.538  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    4    5
CONECT    5    6    7   15
CONECT    6   16   17   18
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for NP0000265 (2-Methyl-3-ketovaleric acid)

CCC(=O)C(C)C(O)=O
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INCHI for NP0000265 (2-Methyl-3-ketovaleric acid)

InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-Methyl-3-oxo-pentanoic acidChEBI
2-Methyl-3-oxovaleric acidChEBI
beta-Ketoisocaproic acidChEBI
2-Methyl-3-oxo-pentanoateGenerator
2-Methyl-3-oxovalerateGenerator
b-KetoisocaproateGenerator
b-Ketoisocaproic acidGenerator
beta-KetoisocaproateGenerator
Β-ketoisocaproateGenerator
Β-ketoisocaproic acidGenerator
2-Methyl-3-ketovalerateGenerator
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
IUPAC Name2-methyl-3-oxopentanoic acid
Traditional Name2-methyl-3-oxovaleric acid
CAS Registry Number14925-93-0
SMILES
CCC(=O)C(C)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyQTLYPQZWYOHATR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Beta-keto acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Beta-hydroxy ketone
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility30 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility60.6 g/LALOGPS
logP0.72ALOGPS
logP1.24ChemAxon
logS-0.33ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.74 m³·mol⁻¹ChemAxon
Polarizability12.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000408
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022024
KNApSAcK IDC00052124
Chemspider ID164251
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5397
PubChem Compound189028
PDB IDNot Available
ChEBI ID86365
Good Scents IDNot Available
References
General References
  1. Kuhara T, Shinka T, Matsuo M, Matsumoto I: Increased excretion of lactate, glutarate, 3-hydroxyisovalerate and 3-methylglutaconate during clinical episodes of propionic acidemia. Clin Chim Acta. 1982 Aug 4;123(1-2):101-9. [PubMed:7116632 ]
  2. Kuhara T, Matsumoto I: Studies on the urinary acidic metabolites from three patients with methylmalonic aciduria. Biomed Mass Spectrom. 1980 Oct;7(10):424-8. [PubMed:6111361 ]
  3. Lehnert W, Junker A: [2-Methyl-3-oxovaleric acid: a characteristic metabolite in propionic acidemia]. Clin Chim Acta. 1980 May 21;104(1):47-51. [PubMed:7389125 ]
  4. DelValle JA, Merinero B, Jimenez A, Garcia MJ, Ugarte M, Omenaca F, Neustadt G, Quero J: Dietary treatment and biochemical studies on a neonatal case of propionyl-CoA carboxylase deficiency. J Inherit Metab Dis. 1982;5(2):121-4. [PubMed:6820422 ]