P. aeruginosa Metabolome Database: 2-Phosphoglyceric acid (PAMDB001814)

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

PAMDB001814

Identification

Name:

2-Phosphoglyceric acid

Description:

2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-(dihydrogen phosphate)Glycerate
2-(dihydrogen phosphate)Glyceric acid
2-(Dihydrogen phosphoric acid)glyceric acid
2-P-D-Glycerate
2-P-D-glyceric acid
2-P-glycerate
2-P-glyceric acid
2-Phospho-(D)-glycerate
2-phospho-(D)-Glyceric acid
2-Phospho-(R)-glycerate
2-phospho-(R)-Glyceric acid
2-Phospho-D-glycerate
2-Phospho-D-glyceric acid
2-phospho-DL-Glycerate
2-Phospho-DL-glyceric acid
2-Phosphoglycerate
3-Hydroxy-2-phosphonooxypropanoate
3-Hydroxy-2-phosphonooxypropanoic acid
D-2-Phosphoglycerate
D-2-Phosphoglyceric acid
D-Glycerate 2-phosphate
D-Glyceric acid 2-phosphoric acid
DL-2-Phosphoglycerate
DL-2-Phosphoglyceric acid
Glycerate 2-phosphate
Glyceric acid 2-phosphate
Glyceric acid 2-phosphoric acid
Phosphoglycerate
Phosphoglyceric acid

Chemical Formula:

C₃H₇O₇P

Average Molecular Weight:

186.0572

Monoisotopic Molecular Weight:

185.99293909

InChI Key:

GXIURPTVHJPJLF-UHFFFAOYSA-N

InChI:

InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)

CAS number:

2553-59-5

IUPAC Name:

3-hydroxy-2-(phosphonooxy)propanoic acid

Traditional IUPAC Name:

2-phosphoglyceric acid

SMILES:

OCC(OP(O)(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Sugar acids and derivatives

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Monoalkyl phosphate
Glyceric_acid
Beta-hydroxy acid
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	20.3 mg/mL	ALOGPS
logP	-2.2	ALOGPS
logP	-1.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	0.81	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.26 m³·mol^-1	ChemAxon
Polarizability	13.37 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:

2-Phosphoglyceric acid + 2-Phosphoglyceric acid > 3-Phosphoglyceric acid + 3-Phosphoglycerate
Phosphoenolpyruvic acid > Water + 2-Phosphoglyceric acid + 2-Phosphoglyceric acid
Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acid

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-9300000000-24ac9683b32428f58197	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9600000000-b12281d6d89eef904e6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a07c4a51c820b32ec8bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-516a86a1a17689399892	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-b33f3e08e2e8b3d5aed5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-07016cc3ecca7d5e323b	View in MoNA

References

References:

Comi GP, Fortunato F, Lucchiari S, Bordoni A, Prelle A, Jann S, Keller A, Ciscato P, Galbiati S, Chiveri L, Torrente Y, Scarlato G, Bresolin N: Beta-enolase deficiency, a new metabolic myopathy of distal glycolysis. Ann Neurol. 2001 Aug;50(2):202-7. Pubmed: 11506403
Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225
Hakobyan D, Nazaryan K: Investigation of interaction between enolase and phosphoglycerate mutase using molecular dynamics simulation. J Biomol Struct Dyn. 2006 Jun;23(6):625-34. Pubmed: 16615808
Mulquiney PJ, Bubb WA, Kuchel PW: Model of 2,3-bisphosphoglycerate metabolism in the human erythrocyte based on detailed enzyme kinetic equations: in vivo kinetic characterization of 2,3-bisphosphoglycerate synthase/phosphatase using 13C and 31P NMR. Biochem J. 1999 Sep 15;342 Pt 3:567-80. Pubmed: 10477268
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
Reed, G. H., Poyner, R. R., Larsen, T. M., Wedekind, J. E., Rayment, I. (1996). "Structural and mechanistic studies of enolase." Curr Opin Struct Biol 6:736-743. Pubmed: 8994873
Reher M, Bott M, Schonheit P: Characterization of glycerate kinase (2-phosphoglycerate forming), a key enzyme of the nonphosphorylative Entner-Doudoroff pathway, from the thermoacidophilic euryarchaeon Picrophilus torridus. FEMS Microbiol Lett. 2006 Jun;259(1):113-9. Pubmed: 16684110
Tsujino S, Shanske S, Sakoda S, Toscano A, DiMauro S: Molecular genetic studies in muscle phosphoglycerate mutase (PGAM-M) deficiency. Muscle Nerve. 1995;3:S50-3. Pubmed: 7603528
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Wang Y, Wei Z, Liu L, Cheng Z, Lin Y, Ji F, Gong W: Crystal structure of human B-type phosphoglycerate mutase bound with citrate. Biochem Biophys Res Commun. 2005 Jun 17;331(4):1207-15. Pubmed: 15883004
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Wold, Finn. L-Glyceric acid monophosphates. Journal of Organic Chemistry (1961), 26 197-9.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	24344
HMDB ID	HMDB00362
Pubchem Compound ID	59
Kegg ID	Not Available
ChemSpider ID	58
Wikipedia	2-Phosphoglycerate
BioCyc ID	Not Available

2-Phosphoglyceric acid (PAMDB001814)

Structure for 2-Phosphoglyceric acid (PAMDB001814)