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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 22:57:05 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
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 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
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentSugar 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 mg/mLALOGPS
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 Area124.29 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m3·mol-1ChemAxon
Polarizability13.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraMS/MS
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.6 +/- 2.5 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified14.0 (9.0-19.0) uMAdult (>18 years old)BothNormal details
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. [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. [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. [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. [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. [7603528 ]
  6. Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. [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. [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. [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. [8994873 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays a major role in regulating hemoglobin oxygen affinity by controlling the levels of its allosteric effector 2,3-bisphosphoglycerate (2,3-BPG). Also exhibits mutase (EC 5.4.2.1) and phosphatase (EC 3.1.3.13) activities.
Gene Name:
BPGM
Uniprot ID:
P07738
Molecular weight:
30004.98
General function:
Involved in catalytic activity
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM2
Uniprot ID:
P15259
Molecular weight:
28765.96
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
General function:
Involved in catalytic activity
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM1
Uniprot ID:
P18669
Molecular weight:
28803.675
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB3
Uniprot ID:
Q16875
Molecular weight:
57286.965
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB4
Uniprot ID:
Q16877
Molecular weight:
54039.34
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB1
Uniprot ID:
P16118
Molecular weight:
54680.86
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB2
Uniprot ID:
O60825
Molecular weight:
54405.88
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK2
Uniprot ID:
P07205
Molecular weight:
44795.79
General function:
Involved in phosphoglycerate kinase activity
Specific function:
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name:
PGK1
Uniprot ID:
P00558
Molecular weight:
44614.36
General function:
Involved in phosphoprotein phosphatase activity
Specific function:
Displays phosphatase activity for serine/threonine residues, and, dephosphorylates and activates MAP3K5 kinase. Has apparently no phosphoglycerate mutase activity. May be regulator of mitochondrial dynamics. Substrate for a KEAP1-dependent ubiquitin ligase complex. Contributes to the repression of NFE2L2-dependent gene expression. Acts as a central mediator for programmed necrosis induced by TNF, by reactive oxygen species and by calcium ionophore.
Gene Name:
PGAM5
Uniprot ID:
Q96HS1
Molecular weight:
32004.11
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM2
Uniprot ID:
A4D2J6
Molecular weight:
28219.3
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM1
Uniprot ID:
Q0D2Q6
Molecular weight:
28791.6
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q53G35
Molecular weight:
28831.7
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM1
Uniprot ID:
Q6FHU2
Molecular weight:
28803.7
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM1
Uniprot ID:
Q6P6D7
Molecular weight:
28819.7