| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-05-29 13:25:58 -0600 |
| HMDB ID |
HMDB00362 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common 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 |
Download:
MOL |
SDF |
PDB |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 2-(Dihydrogen phosphate)Glycerate
- 2-(Dihydrogen phosphate)Glyceric acid
- 2-P-D-Glycerate
- 2-P-D-Glyceric acid
- 2-P-Glycerate
- 2-P-Glyceric acid
- 2-Phospho-D-glycerate
- 2-Phospho-DL-glyceric acid
- 2-Phosphoglycerate
- 2-Phosphoglyceric acid
- 3-Hydroxy-2-phosphonooxypropanoate
- 3-Hydroxy-2-phosphonooxypropanoic acid
- DL-2-Phosphoglycerate
- Glycerate 2-phosphate
- Glyceric acid 2-phosphate
- Phosphoglycerate
|
| Chemical Formula |
C3H7O7P |
| Average Molecular Weight |
186.0572 |
| Monoisotopic Molecular Weight |
185.99293909 |
| IUPAC Name |
3-hydroxy-2-(phosphonooxy)propanoic acid |
| Traditional IUPAC Name |
2-phosphoglyceric acid |
| CAS Registry Number |
2553-59-5 |
| SMILES |
OCC(OP(O)(O)=O)C(O)=O |
| InChI Identifier |
InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9) |
| InChI Key |
GXIURPTVHJPJLF-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Sugar Acids and Derivatives |
| Sub Class |
N/A |
| Other Descriptors |
- 2-phosphoglyceric acid(ChEBI)
- Aliphatic Acyclic Compounds
- Beta Hydroxy Acids and Derivatives
|
| Substituents |
- Carboxylic Acid
- Organic Hypophosphite
- Organic Phosphite
- Phosphoric Acid Ester
- Primary Alcohol
|
| Direct Parent |
Sugar Acids and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available
|
| Application |
Not Available
|
| Cellular locations |
Not Available
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
|
| Biofluid Locations |
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.6 +/- 2.5 uM |
Newborn (0-30 days old) |
Both |
Normal
|
|
| Cellular Cytoplasm |
Detected and Quantified |
|
14.0 (9.0-19.0) uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023161 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
58 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
2-PG |
| BiGG ID |
Not Available |
| Wikipedia Link |
2-Phosphoglycerate |
| NuGOwiki Link |
HMDB00362 |
| Metagene Link |
HMDB00362 |
| METLIN ID |
5351 |
| PubChem Compound |
59 |
| PDB ID |
1EQJ |
| ChEBI ID |
24344 |
| References |
|---|
| Synthesis Reference |
Wold, Finn. L-Glyceric acid monophosphates. Journal of Organic Chemistry (1961), 26 197-9. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- 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
- 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
- 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
- Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8.
Pubmed: 8753225
- 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
- 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
- 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
- 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
- Reed GH, Poyner RR, Larsen TM, Wedekind JE, Rayment I: Structural and mechanistic studies of enolase. Curr Opin Struct Biol. 1996 Dec;6(6):736-43.
Pubmed: 8994873
|
