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Identification
YMDB IDYMDB00376
Name(R)-Pantoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(R)-Pantoic acid is an intermediate in the phosphopantothenate biosynthesis pathway for the de novo synthesis of R-pantothenate (vitamin B5) from valine in plants and microorganisms. [Biocyc PANTO-PWY]
Structure
Thumb
Synonyms
  • (R)-Pantoate
  • Pantoate
  • Pantoic acid
  • (R)-Pantoic acid
CAS number470-29-1
WeightAverage: 148.1571
Monoisotopic: 148.073558872
InChI KeyOTOIIPJYVQJATP-BYPYZUCNSA-N
InChIInChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1
IUPAC Name(2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid
Traditional IUPAC Name(R)-pantoic acid
Chemical FormulaC6H12O4
SMILESCC(C)(CO)[C@@H](O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Branched fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility308 g/LALOGPS
logP-0.59ALOGPS
logP-0.49ChemAxon
logS0.32ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.01 m³·mol⁻¹ChemAxon
Polarizability14.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
beta-Alanine metabolismec00410 Map00410
SMPDB ReactionsNot Available
KEGG Reactions
2-Dehydropantoic acid + NADPH + hydronNADP + (R)-Pantoic acid
Adenosine triphosphate + (R)-Pantoic acid + Beta-AlanineAdenosine monophosphate + Pyrophosphate + (R)-Pantothenic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18697
HMDB IDNot Available
Pubchem Compound ID439251
Kegg IDC00522
ChemSpider ID388387
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ILV5
Uniprot ID:
P06168
Molecular weight:
44368.10156
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 oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:
PAN5
Uniprot ID:
P38787
Molecular weight:
42820.89844
Reactions
(R)-pantoate + NADP(+) → 2-dehydropantoate + NADPH.
General function:
Involved in pantoate-beta-alanine ligase activity
Specific function:
Required for pantothenic acid biosynthesis
Gene Name:
PAN6
Uniprot ID:
P40459
Molecular weight:
35031.89844
Reactions
ATP + (R)-pantoate + beta-alanine → AMP + diphosphate + (R)-pantothenate.