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2-Oxo-3-hydroxy-4-phosphobutanoic acid (YMDB00384)

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 (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate or alpha-keto-3-hydroxy-4-phosphobutyrate, 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; which is catalyzed by 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 through the action of 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
MOLSDFPDBSMILESInChI
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 + NAD → NADH + hydron + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid ↔ O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
KEGG Reactions
L-Glutamic acid + 2-Oxo-3-hydroxy-4-phosphobutanoic acid ↔ Oxoglutaric acid + O-Phospho-4-hydroxy-L-threonine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-db85b7397058e1ec03b8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0005-9121000000-aee0eaf4d81dbd99259bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1930000000-9c3c35aa2de551b4bbf2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-4900000000-162b52e552d9157d3bbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9300000000-abe9d170b8c46a45e858JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0329-9730000000-c5dda701292450f19043JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-1880b6c8035cdbc2520fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8b44e7c9ed6f8dcaee86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9020000000-7708f7e46e45e30974c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e2b487fed3fe6cdfcc08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-3541ae70498a829692b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9000000000-51318a1b7c455a5670bbJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 IDFDB030351
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphoserine aminotransferase
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.