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Record Information
Version	2.0
Creation Date	2012-05-31 14:03:10 -0600
Update Date	2015-09-17 15:42:02 -0600
Secondary Accession Numbers	ECMDB04043
Identification
Name:	2-Dehydropantoate
Description	2-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa917b994> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Short-chain keto acids and derivatives
Direct Parent	Short-chain keto acids and derivatives
Alternative Parents	Methyl-branched fatty acids Hydroxy fatty acids Beta-hydroxy ketones Alpha-keto acids and derivatives Alpha-hydroxy ketones Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	oxo monocarboxylic acid (CHEBI:17094 ) hydroxy monocarboxylic acid (CHEBI:17094 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 109 g/L ALOGPS logP -0.35 ALOGPS logP 0.58 ChemAxon logS -0.13 ALOGPS pKa (Strongest Acidic) 3.25 ChemAxon pKa (Strongest Basic) -2.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 33.47 m³·mol⁻¹ ChemAxon Polarizability 13.83 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate alpha-Ketoisovaleric acid + Water + 5,10-Methylene-THF + a-Ketoisovaleric acid <> 2-Dehydropantoate + Tetrahydrofolic acid 5,10-Methylene-THF + alpha-Ketoisovaleric acid + Water <> Tetrahydrofolic acid + 2-Dehydropantoate (R)-Pantoate + NADP <> 2-Dehydropantoate + NADPH + Hydrogen ion (R)-Pantoate + NADP < Hydrogen ion + 2-Dehydropantoate + NADPH 5,10-Methylene-THF + a-Ketoisovaleric acid + Water > Tetrahydrofolic acid + 2-Dehydropantoate (R)-Pantoate + NADP > 2-Dehydropantoate + NADPH 2-dehydropantoate + NADPH + Hydrogen ion + 2-Dehydropantoate + NADPH > NADP + (R)-pantoate + (R)-Pantoate a-Ketoisovaleric acid + 5,10-Methylene-THF + Water + 5,10-Methylene-THF > Tetrahydrofolic acid + 2-dehydropantoate + Tetrahydrofolic acid + 2-Dehydropantoate 2 2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate alpha-Ketoisovaleric acid + Water + 5 5,10-Methylene-THF + a-Ketoisovaleric acid <>2 2-Dehydropantoate + Tetrahydrofolic acid 2 2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate
SMPDB Pathways:	Pantothenate and CoA biosynthesis PW000828
KEGG Pathways:	Metabolic pathways eco01100 Pantothenate and CoA biosynthesis ec00770
EcoCyc Pathways:	phosphopantothenate biosynthesis I PANTO-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00di-9300000000-21671ab14de5342f1185 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fba-1900000000-65021b449e2495c02885 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fk9-9600000000-094d64c5b115d0ef1bb6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00dl-9100000000-e52d8a1685278ec9f7b6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f6t-1900000000-f912860fc8aba37cf980 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0gi1-7900000000-cd2194ab1aec775efa09 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-01b9-9100000000-e74573027b9636f2c922 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004r-4900000000-473fb2fde1bc77d59c76 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05fr-9000000000-874b2513b4eef1599bed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052f-9000000000-07d66309a39c6a4c42a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-2900000000-3ee21bf40b0c9d2e5c44 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01ba-9200000000-442c33f9de33eb4f24d0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00xr-9000000000-6b2df4e05ef546297ed7 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 17094 HMDB ID HMDB0304068 Pubchem Compound ID 38 Kegg ID C00966 ChemSpider ID 37 Wikipedia ID Not Available BioCyc ID 2-DEHYDROPANTOATE EcoCyc ID 2-DEHYDROPANTOATE Ligand Expo KPL

Enzymes