2-Oxo-3-hydroxy-4-phosphobutanoic acid (ECMDB06801) (M2MDB000690)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (334)
Record Information
Version2.0
Creation Date2012-05-31 14:09:24 -0600
Update Date2015-06-03 15:54:54 -0600
Secondary Accession Numbers
  • ECMDB06801
Identification
Name:2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description2-Oxo-3-hydroxy-4-phosphobutanoic acid is involved in the interconversion of O-phospho-4-hydroxy-L-threonine. This reaction is catalyzed by phosphoserine aminotransferase 1. These amino acid derivatives are sometimes considered to be part of the vitamin B6 pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (3R)-3-hydroxy-2-oxo-4 phosphonooxybutanoate
  • (3R)-3-hydroxy-2-oxo-4 phosphonooxybutanoic acid
  • (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
  • 3-hydroxy-4-phospho-hydroxy-α-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-a-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-a-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-alpha-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-alpha-ketobutyric acid
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyrate
  • 3-Hydroxy-4-phospho-hydroxy-α-ketobutyric acid
  • a-keto-3-Hydroxy-4-phosphobutyrate
  • a-keto-3-Hydroxy-4-phosphobutyric acid
  • Alpha-Keto-3-hydroxy-4-phosphobutyrate
  • Alpha-Keto-3-hydroxy-4-phosphobutyric acid
  • α-keto-3-Hydroxy-4-phosphobutyrate
  • α-keto-3-Hydroxy-4-phosphobutyric acid
Chemical Formula:C4H7O8P
Weight:Average: 214.0673
Monoisotopic: 213.987853712
InChI Key:MZJFVXDTNBHTKZ-UWTATZPHSA-N
InChI:InChI=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
CAS number:Not Available
IUPAC Name:(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name:(3R)-3-hydroxy-2-oxo-4-(phosphonooxy)butanoic acid
SMILES:O[C@H](COP(O)(O)=O)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.
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
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
O-Phospho-4-hydroxy-L-threonine + alpha-Ketoglutarate <> 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate
4-Phospho-D-erythronate + NAD > Hydrogen ion + 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
4-Phospho-D-erythronate + NAD > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH
O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate
Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> A-Ketoglutaric acid oxime + O-Phospho-4-hydroxy-L-threonine
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
4 4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH +2 2-Oxo-3-hydroxy-4-phosphobutanoic acid
L-Glutamate + 2 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
4 4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH +2 2-Oxo-3-hydroxy-4-phosphobutanoic acid
SMPDB Pathways:
Vitamin B6 1430936196PW000891 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-db85b7397058e1ec03b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0005-9121000000-aee0eaf4d81dbd99259bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1930000000-9c3c35aa2de551b4bbf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-4900000000-162b52e552d9157d3bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9300000000-abe9d170b8c46a45e858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0329-9730000000-c5dda701292450f19043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-1880b6c8035cdbc2520fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8b44e7c9ed6f8dcaee86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9020000000-7708f7e46e45e30974c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e2b487fed3fe6cdfcc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-3541ae70498a829692b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9000000000-51318a1b7c455a5670bbView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27951
HMDB IDHMDB06801
Pubchem Compound ID21145142
Kegg IDC06054
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID3OH-4P-OH-ALPHA-KETOBUTYRATE
EcoCyc ID3OH-4P-OH-ALPHA-KETOBUTYRATE

Enzymes

Protein Details
1. Erythronate-4-phosphate dehydrogenase
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the oxidation of erythronate-4-phosphate to 3- hydroxy-2-oxo-4-phosphonooxybutanoate
Gene Name:
pdxB
Uniprot ID:
P05459
Molecular weight:
41367
Reactions
4-phospho-D-erythronate + NAD(+) = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + NADH.
Protein Details
2. 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. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Uniprot ID:
P23721
Molecular weight:
39783
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.