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Record Information
Version	2.0
Creation Date	2012-05-31 14:23:02 -0600
Update Date	2015-09-17 15:42:03 -0600
Secondary Accession Numbers	ECMDB20016
Identification
Name:	(R)-Pantoate
Description	(r)-pantoate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)Pantoic acid is an alpha hydroxy acid which is a component of some biologically active compounds. The amide of pantoic acid with alanine is pantothenic acid (vitamin B5) and the amide with β-alanine is the pharmaceutical drug hopantenic acid. It is also a central component of coenzyme A. (WikiPedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae7730a4> Close
Synonyms:	(2R)-2,4-dihydroxy-3,3-dimethylbutanoate (2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid (R)-Pantoic acid 2,4-DIHYDROXY-3,3-DIMETHYL-BUTYRATE 2,4-DIHYDROXY-3,3-dimethyl-butyric acid L-Pantoate L-Pantoic acid PAF Pantoate Pantoic acid
Chemical Formula:	C6H11O4
Weight:	Average: 147.151 Monoisotopic: 147.066282414
InChI Key:	OTOIIPJYVQJATP-UHFFFAOYSA-M
InChI:	InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/p-1
CAS number:	470-29-1
IUPAC Name:	(2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid
Traditional IUPAC Name:	(R)-pantoic acid
SMILES:	CC(C)(CO)C(O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Hydroxy fatty acids
Alternative Parents	Short-chain hydroxy acids and derivatives Methyl-branched fatty acids Monosaccharides Alpha hydroxy acids and derivatives Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Branched fatty acid Methyl-branched fatty acid Short-chain hydroxy acid Hydroxy fatty acid Alpha-hydroxy acid Hydroxy acid Monosaccharide Secondary alcohol Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Hydrocarbon derivative Alcohol Carbonyl group Organic oxide Primary alcohol Organic oxygen compound Organooxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	pantoic acid (CHEBI:18697 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 308 g/L ALOGPS logP -0.59 ALOGPS logP -0.49 ChemAxon logS 0.32 ALOGPS pKa (Strongest Acidic) 3.96 ChemAxon pKa (Strongest Basic) -2.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 77.76 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 34.01 m³·mol⁻¹ ChemAxon Polarizability 14.36 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 beta-Alanine + Adenosine triphosphate + (R)-Pantoate <> Adenosine monophosphate + Hydrogen ion + Pantothenic acid + Pyrophosphate (R)-Pantoate + NADP <> 2-Dehydropantoate + NADPH + Hydrogen ion Adenosine triphosphate + (R)-Pantoate + beta-Alanine <> Adenosine monophosphate + Pyrophosphate + Pantothenic acid (R)-Pantoate + NADP < Hydrogen ion + 2-Dehydropantoate + NADPH beta-Alanine + (R)-Pantoate + Adenosine triphosphate > Hydrogen ion + Pantothenic acid + Pyrophosphate + Adenosine monophosphate Adenosine triphosphate + (R)-Pantoate + beta-Alanine > Adenosine monophosphate + Pyrophosphate + (R)-pantothenate (R)-Pantoate + NADP > 2-Dehydropantoate + NADPH 2-dehydropantoate + NADPH + Hydrogen ion + 2-Dehydropantoate + NADPH > NADP + (R)-pantoate + (R)-Pantoate beta-Alanine + Adenosine triphosphate + (R)-pantoate + (R)-Pantoate > Adenosine monophosphate + Pyrophosphate + Hydrogen ion + Pantothenic acid + Pantothenic acid 2 2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate beta-Alanine + Adenosine triphosphate + (R)-Pantoate <> Adenosine monophosphate + Hydrogen ion + Pantothenic acid + Pyrophosphate Adenosine triphosphate + (R)-Pantoate + beta-Alanine <> Adenosine monophosphate + Pyrophosphate 2 2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate beta-Alanine + Adenosine triphosphate + (R)-Pantoate <> Adenosine monophosphate + Hydrogen ion + Pantothenic acid + Pyrophosphate
SMPDB Pathways:	Pantothenate and CoA biosynthesis PW000828 beta-Alanine metabolism PW000896
KEGG Pathways:	Metabolic pathways eco01100 Pantothenate and CoA biosynthesis ec00770 beta-Alanine metabolism ec00410
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 splash10-00e9-9300000000-1533cf69a587ccbc946b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-1900000000-7d32d9fe2f4c45ee7840 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fk9-9500000000-27fa4de1f52b9b39c2c7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0abc-9100000000-4b387706b53ffaba5f68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f6t-2900000000-ea603b384234b8b971d2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-9600000000-c12f5dc91e63440b6213 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00di-9000000000-921e587537e7f7b8173d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-1900000000-d6c062a26d684557b37c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00ba-9500000000-a1678e241f40c3991ed8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-05i3-9000000000-ff04a60d16aa9928a044 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001r-4900000000-8f94035a9aca264573f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-074i-9100000000-d5f8b375fb7c5c114d19 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052f-9000000000-eff6aae246d496dfde6f 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 14737 HMDB ID HMDB0240389 Pubchem Compound ID 5289105 Kegg ID C00522 ChemSpider ID 825 Wikipedia ID Pantoic acid BioCyc ID L-PANTOATE EcoCyc ID L-PANTOATE Ligand Expo PAF

Enzymes