P. aeruginosa Metabolome Database: 2-Oxo-3-hydroxy-4-phosphobutanoic acid (PAMDB000690)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000690

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

214.0673

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Substituents

Monoalkyl phosphate
Short-chain keto acid
Beta-hydroxy acid
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Hydroxy acid
Beta-ketoaldehyde
Alpha-keto acid
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.6 m³·mol^-1	ChemAxon
Polarizability	15.26 Å³	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
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
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

Pathways:

Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Vitamin B6 metabolism pae00750

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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

2-Oxo-3-hydroxy-4-phosphobutanoic acid (PAMDB000690)

Structure for 2-Oxo-3-hydroxy-4-phosphobutanoic acid (PAMDB000690)