Human Metabolome Database Version 3.5

Showing metabocard for 2-Phosphoglyceric acid (HMDB00362)

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 Link_out, Wikipedia).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(Dihydrogen phosphate)Glycerate
  2. 2-(Dihydrogen phosphate)Glyceric acid
  3. 2-P-D-Glycerate
  4. 2-P-D-Glyceric acid
  5. 2-P-Glycerate
  6. 2-P-Glyceric acid
  7. 2-Phospho-D-glycerate
  8. 2-Phospho-DL-glyceric acid
  9. 2-Phosphoglycerate
  10. 2-Phosphoglyceric acid
  11. 3-Hydroxy-2-phosphonooxypropanoate
  12. 3-Hydroxy-2-phosphonooxypropanoic acid
  13. DL-2-Phosphoglycerate
  14. Glycerate 2-phosphate
  15. Glyceric acid 2-phosphate
  16. 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
  • Endogenous
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
Property Value Source
Water Solubility 20.3 g/L ALOGPS
LogP -2.24 ALOGPS
LogP -1.6 ChemAxon
LogS -0.96 ALOGPS
pKa (strongest acidic) 0.81 ChemAxon
pKa (strongest basic) -3.1 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 124.29 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 31.26 ChemAxon
Polarizability 13.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.6 +/- 2.5 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
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
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 Link_out
KEGG Compound ID Not Available
BioCyc ID 2-PG Link_out
BiGG ID Not Available
Wikipedia Link 2-Phosphoglycerate Link_out
NuGOwiki Link HMDB00362 Link_out
Metagene Link HMDB00362 Link_out
METLIN ID 5351 Link_out
PubChem Compound 59 Link_out
PDB ID 1EQJ Link_out
ChEBI ID 24344 Link_out
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
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out

Enzymes
Name: Bisphosphoglycerate mutase
Reactions: Not Available
Gene Name: BPGM
Uniprot ID: P07738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase 2
Reactions: Not Available
Gene Name: PGAM2
Uniprot ID: P15259 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phosphoglycerate mutase 4
Reactions: Not Available
Gene Name: PGAM4
Uniprot ID: Q8N0Y7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase 1
Reactions: Not Available
Gene Name: PGAM1
Uniprot ID: P18669 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3
Reactions: Not Available
Gene Name: PFKFB3
Uniprot ID: Q16875 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4
Reactions: Not Available
Gene Name: PFKFB4
Uniprot ID: Q16877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
Reactions: Not Available
Gene Name: PFKFB1
Uniprot ID: P16118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2
Reactions: Not Available
Gene Name: PFKFB2
Uniprot ID: O60825 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate kinase 2
Reactions: Not Available
Gene Name: PGK2
Uniprot ID: P07205 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate kinase 1
Reactions: Not Available
Gene Name: PGK1
Uniprot ID: P00558 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine/threonine-protein phosphatase PGAM5, mitochondrial
Reactions: Not Available
Gene Name: PGAM5
Uniprot ID: Q96HS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase
Reactions: Not Available
Gene Name: PGAM2
Uniprot ID: A4D2J6 Link_out
Protein Sequence: FASTA
Name: Phosphoglycerate mutase
Reactions: Not Available
Gene Name: PGAM1
Uniprot ID: Q0D2Q6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: Q53G35 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase
Reactions: Not Available
Gene Name: PGAM1
Uniprot ID: Q6FHU2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase
Reactions: Not Available
Gene Name: PGAM1
Uniprot ID: Q6P6D7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA