Record Information
Version2.0
Creation Date2012-05-31 14:03:10 -0600
Update Date2015-09-17 15:42:02 -0600
Secondary Accession Numbers
  • ECMDB04043
Identification
Name:2-Dehydropantoate
Description2-dehydropantoate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)2-dehydropantoate is invovled in Pantothenate and CoA biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)
Structure
Thumb
Synonyms:
  • 2-Dehydropantoic acid
  • 2-Keto-pantoate
  • 2-Keto-pantoic acid
  • 2DHPA
  • Ketopantoate
  • Ketopantoic acid
Chemical Formula:C6H9O4
Weight:Average: 145.1333
Monoisotopic: 145.050083776
InChI Key:PKVVTUWHANFMQC-UHFFFAOYSA-M
InChI:InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)/p-1
CAS number:Not Available
IUPAC Name:4-hydroxy-3,3-dimethyl-2-oxobutanoic acid
Traditional IUPAC Name:ketopantoic acid
SMILES:CC(C)(CO)C(=O)C([O-])=O
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
  • Hydroxy fatty acid
  • Short-chain keto acid
  • Methyl-branched fatty acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility109 g/LALOGPS
logP-0.35ALOGPS
logP0.58ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.47 m³·mol⁻¹ChemAxon
Polarizability13.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9300000000-21671ab14de5342f1185View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fba-1900000000-65021b449e2495c02885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-9600000000-094d64c5b115d0ef1bb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9100000000-e52d8a1685278ec9f7b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1900000000-f912860fc8aba37cf980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi1-7900000000-cd2194ab1aec775efa09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-9100000000-e74573027b9636f2c922View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17094
HMDB IDNot Available
Pubchem Compound ID38
Kegg IDC00966
ChemSpider ID37
Wikipedia IDNot Available
BioCyc ID2-DEHYDROPANTOATE
EcoCyc ID2-DEHYDROPANTOATE
Ligand ExpoKPL

Enzymes

General function:
Involved in oxidation-reduction process
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ilvC
Uniprot ID:
P05793
Molecular weight:
54069
Reactions
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) = (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.
General function:
Involved in oxidation-reduction process
Specific function:
Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:
panE
Uniprot ID:
P0A9J4
Molecular weight:
33871
Reactions
(R)-pantoate + NADP(+) = 2-dehydropantoate + NADPH.
General function:
Involved in 3-methyl-2-oxobutanoate hydroxymethyltransferase activity
Specific function:
Catalyzes the reversible reaction in which hydroxymethyl group from 5,10-methylenetetrahydrofolate is tranferred onto alpha-ketoisovalerate to form ketopantoate
Gene Name:
panB
Uniprot ID:
P31057
Molecular weight:
28237
Reactions
5,10-methylenetetrahydrofolate + 3-methyl-2-oxobutanoate + H(2)O = tetrahydrofolate + 2-dehydropantoate.