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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:45 UTC
HMDB IDHMDB0000362
Secondary Accession Numbers
  • HMDB00362
  • HMDB0062707
  • HMDB62707
Metabolite Identification
Common Name2-Phosphoglyceric acid
Description2-Phosphoglyceric acid belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. 2-Phosphoglyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phosphoglyceric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Phosphoglyceric acid has been detected, but not quantified in, milk (cow). This could make 2-phosphoglyceric acid a potential biomarker for the consumption of these foods. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate.
Structure
Thumb
Synonyms
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
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Glyceric_acid
  • Monoalkyl phosphate
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg124.030932474
[M-H]-Baker127.64930932474
[M-H]-Not Available125.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000523
[M+H]+Not Available134.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000523
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023161
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Phosphoglyceric_acid
METLIN IDNot Available
PubChem Compound59
PDB IDNot Available
ChEBI ID24344
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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;2:18. [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 Suppl. 1995;3:S50-3. [PubMed:7603528 ]
  6. Fujii H: [Red cell glycolytic intermediates]. Nihon 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 ]

Only showing the first 10 proteins. There are 16 proteins in total.

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

Only showing the first 10 proteins. There are 16 proteins in total.