Showing metabocard for 2-Phosphoglyceric acid (HMDB00362)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (16) Show 16 proteinsXML
enzymes (16) Show 16 proteins
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:58 UTC
HMDB IDHMDB00362
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Phosphoglyceric acid
Description2-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
Thumb
MOLSDFPDBSMILESInChIView 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 FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name3-hydroxy-2-(phosphonooxy)propanoic acid
Traditional IUPAC Name2-phosphoglyceric acid
CAS Registry Number2553-59-5
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 KeyGXIURPTVHJPJLF-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassN/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 ParentSugar Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility20.3 g/LALOGPS
logP-2.2ALOGPS
logP-1.6ChemAxon
logS-0.96ALOGPS
pKa (strongest acidic)0.81ChemAxon
pKa (strongest basic)-3.1ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count4ChemAxon
polar surface area124.29ChemAxon
rotatable bond count4ChemAxon
refractivity31.26ChemAxon
polarizability13.37ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified1.6 +/- 2.5 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified14.0 (9.0-19.0) uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023161
KNApSAcK IDNot Available
Chemspider ID58
KEGG Compound IDNot Available
BioCyc ID2-PG
BiGG IDNot Available
Wikipedia Link2-Phosphoglycerate
NuGOwiki LinkHMDB00362
Metagene LinkHMDB00362
METLIN ID5351
PubChem Compound59
PDB ID1EQJ
ChEBI ID24344
References
Synthesis ReferenceWold, 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225
  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
  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
  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

Enzymes

1. Bisphosphoglycerate mutase
Gene Name:
BPGM
Uniprot ID:
P07738
2. Phosphoglycerate mutase 2
Gene Name:
PGAM2
Uniprot ID:
P15259
3. Probable phosphoglycerate mutase 4
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
4. Phosphoglycerate mutase 1
Gene Name:
PGAM1
Uniprot ID:
P18669
5. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3
Gene Name:
PFKFB3
Uniprot ID:
Q16875
6. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4
Gene Name:
PFKFB4
Uniprot ID:
Q16877
7. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
Gene Name:
PFKFB1
Uniprot ID:
P16118
8. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2
Gene Name:
PFKFB2
Uniprot ID:
O60825
9. Phosphoglycerate kinase 2
Gene Name:
PGK2
Uniprot ID:
P07205
10. Phosphoglycerate kinase 1
Gene Name:
PGK1
Uniprot ID:
P00558
11. Serine/threonine-protein phosphatase PGAM5, mitochondrial
Gene Name:
PGAM5
Uniprot ID:
Q96HS1
12. Phosphoglycerate mutase
Gene Name:
PGAM2
Uniprot ID:
A4D2J6
13. Phosphoglycerate mutase
Gene Name:
PGAM1
Uniprot ID:
Q0D2Q6
14. Phosphoglycerate mutase
Gene Name:
Not Available
Uniprot ID:
Q53G35
15. Phosphoglycerate mutase
Gene Name:
PGAM1
Uniprot ID:
Q6FHU2
16. Phosphoglycerate mutase
Gene Name:
PGAM1
Uniprot ID:
Q6P6D7