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Record Information
Version	2.0
Creation Date	2012-05-31 14:09:24 -0600
Update Date	2015-06-03 15:54:54 -0600
Secondary Accession Numbers	ECMDB06801
Identification
Name:	2-Oxo-3-hydroxy-4-phosphobutanoic acid
Description	2-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9c7389c> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Short-chain keto acids and derivatives
Direct Parent	Short-chain keto acids and derivatives
Alternative Parents	Monoalkyl phosphates Beta hydroxy acids and derivatives Monosaccharides Alpha-keto acids and derivatives Acyloins Alpha-hydroxy ketones Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	2-oxo monocarboxylic acid (CHEBI:27951 ) 3-hydroxy monocarboxylic acid (CHEBI:27951 ) carboxyalkyl phosphate (CHEBI:27951 ) oxoalkyl phosphate (CHEBI:27951 ) hydroxyalkyl phosphate (CHEBI:27951 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 16.2 g/L ALOGPS logP -2 ALOGPS logP -1.4 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.34 ChemAxon pKa (Strongest Basic) -4 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 141.36 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 36.6 m³·mol⁻¹ ChemAxon Polarizability 15.26 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:	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 1430936196 PW000891
KEGG Pathways:	Glycine, serine and threonine metabolism ec00260 Metabolic pathways eco01100 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Vitamin B6 metabolism ec00750
EcoCyc Pathways:	pyridoxal 5'-phosphate biosynthesis I PYRIDOXSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9300000000-db85b7397058e1ec03b8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0005-9121000000-aee0eaf4d81dbd99259b 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 splash10-01ot-1930000000-9c3c35aa2de551b4bbf2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00ke-4900000000-162b52e552d9157d3bbb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0005-9300000000-abe9d170b8c46a45e858 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0329-9730000000-c5dda701292450f19043 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9200000000-1880b6c8035cdbc2520f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-8b44e7c9ed6f8dcaee86 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-9020000000-7708f7e46e45e30974c6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-9000000000-e2b487fed3fe6cdfcc08 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9100000000-3541ae70498a829692b2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000w-9000000000-51318a1b7c455a5670bb 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 27951 HMDB ID HMDB06801 Pubchem Compound ID 21145142 Kegg ID C06054 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID 3OH-4P-OH-ALPHA-KETOBUTYRATE EcoCyc ID 3OH-4P-OH-ALPHA-KETOBUTYRATE

Enzymes