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Identification
YMDB IDYMDB00384
Name2-Oxo-3-hydroxy-4-phosphobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Oxo-3-hydroxy-4-phosphobutanoic acid, also known as alpha-keto-3-hydroxy-4-phosphobutyrate or (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate, 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. 2-Oxo-3-hydroxy-4-phosphobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Oxo-3-hydroxy-4-phosphobutanoic acid exists in all living species, ranging from bacteria to humans. Within yeast, 2-oxo-3-hydroxy-4-phosphobutanoic acid participates in a number of enzymatic reactions. In particular, 2-oxo-3-hydroxy-4-phosphobutanoic acid can be biosynthesized from 4-phospho-D-erythronate through its interaction with the enzyme erythronate-4-phosphate dehydrogenase. In addition, 2-oxo-3-hydroxy-4-phosphobutanoic acid and L-glutamic acid can be converted into O-phospho-4-hydroxy-L-threonine and oxoglutaric acid; which is catalyzed by the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. In yeast, 2-oxo-3-hydroxy-4-phosphobutanoic acid is involved in the metabolic pathway called the vitamin B6 pathway.
Structure
Thumb
Synonyms
  • (3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoate
  • (3R)-3-Hydroxy-2-oxo-4-phosphonooxybutanoic acid
  • 2-Oxo-3-hydroxy-4-phosphobutanoate
  • 2-Oxo-3-hydroxy-4-phosphobutanoic acid
  • alpha-Keto-3-hydroxy-4-phosphobutyrate
  • (3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoate
  • a-Keto-3-hydroxy-4-phosphobutyrate
  • a-Keto-3-hydroxy-4-phosphobutyric acid
  • alpha-Keto-3-hydroxy-4-phosphobutyric acid
  • Α-keto-3-hydroxy-4-phosphobutyrate
  • Α-keto-3-hydroxy-4-phosphobutyric acid
  • (3R)-3-Hydroxy-2-oxo-4-phosphooxybutanoic acid
CAS numberNot Available
WeightAverage: 214.0673
Monoisotopic: 213.987853712
InChI KeyMZJFVXDTNBHTKZ-UWTATZPHSA-N
InChIInChI=1S/C4H7O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2,5H,1H2,(H,7,8)(H2,9,10,11)/t2-/m1/s1
IUPAC Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Chemical FormulaC4H7O8P
SMILES[H]OC(=O)C(=O)[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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
  • Monoalkyl phosphate
  • Short-chain keto acid
  • Beta-hydroxy acid
  • Acyloin
  • Alpha-keto acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility16.2 g/LALOGPS
logP-2ALOGPS
logP-1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.34ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Vitamin B6PW002488 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
4-Phospho-D-erythronate + NADNADH + hydron + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acidO-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
KEGG Reactions
L-Glutamic acid + 2-Oxo-3-hydroxy-4-phosphobutanoic acidOxoglutaric acid + O-Phospho-4-hydroxy-L-threonine
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 ID27951
HMDB IDHMDB06801
Pubchem Compound ID112
Kegg IDC06054
ChemSpider ID24785138
FOODB IDFDB024087
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine
Gene Name:
SER1
Uniprot ID:
P33330
Molecular weight:
43415.19922
Reactions
O-phospho-L-serine + 2-oxoglutarate → 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate → (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.