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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 20:03:00 UTC
Update Date2020-02-26 21:24:34 UTC
HMDB IDHMDB0003391
Secondary Accession Numbers
  • HMDB03391
Metabolite Identification
Common Name2-Phospho-D-glyceric acid
Description2-Phospho-D-glyceric acid, also known as 2-phospho-D-glycerate or D-glycerate 2-phosphate, 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. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase. 2-Phospho-D-glyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phospho-D-glyceric acid exists in all living species, ranging from bacteria to humans. Within humans, 2-phospho-D-glyceric acid participates in a number of enzymatic reactions. In particular, 2-phospho-D-glyceric acid can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme phosphoglycerate mutase 2. In addition, 2-phospho-D-glyceric acid can be converted into phosphoenolpyruvic acid; which is catalyzed by the enzyme Alpha-enolase. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. In humans, 2-phospho-D-glyceric acid is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Outside of the human body, 2-Phospho-D-glyceric acid has been detected, but not quantified in, rices. This could make 2-phospho-D-glyceric acid a potential biomarker for the consumption of these foods. 2-Phospho-D-glyceric acid or 2PG is an intermediate in gluconeogenesis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate.
Structure
Data?1582752274
Synonyms
ValueSource
2-Phospho-D-glycerateChEBI
2-PHOSPHOGLYCERIC ACIDChEBI
D-Glycerate 2-phosphateChEBI
2-Phospho-(R)-glycerateKegg
2-PHOSPHOGLYCERateGenerator
D-Glyceric acid 2-phosphoric acidGenerator
2-Phospho-(R)-glyceric acidGenerator
(2R)-3-Hydroxy-2-(phosphonooxy)propanoateHMDB
(2R)-3-Hydroxy-2-(phosphonooxy)propanoic acidHMDB
3-D-Hydroxy-2-phosphonooxy-propanoateHMDB
3-D-Hydroxy-2-phosphonooxy-propanoic acidHMDB
D-(+)-2-Phosphoglyceric acidHMDB
D-2-Phosphoglyceric acidHMDB
D-Glyceric acid 2-phosphateHMDB
2-Phospho-D-glyceric acidHMDB
Chemical FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
Traditional Name(+-)-2-phosphoglycerate
CAS Registry Number3443-57-0
SMILES
OC[C@@H](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)/t2-/m1/s1
InChI KeyGXIURPTVHJPJLF-UWTATZPHSA-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m³·mol⁻¹ChemAxon
Polarizability13.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014j-1986100000-67b36247ae0c01d6630fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-1986100000-67b36247ae0c01d6630fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-8ec7a644e48af8fc9f44Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9030000000-cc4abc5e01c64cff2d87Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-80caf2498862e856c8fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-1518e606c03a8697d1b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-66ec419add3cb3e1fd32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-b7f464912df9166dc597Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d09faea5291df7a04b70Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-0900000000-09027263f64d0e1059c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-8eeb1d2a8432d1e44448Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f6t-8900000000-3b714e664b948f61ac7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0023-9000000000-ed83591fbfd15323cd6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001m-9000000000-39cdf9729f381069e45fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-9300000000-24ac9683b32428f58197Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9600000000-b12281d6d89eef904e6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-a07c4a51c820b32ec8bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-516a86a1a17689399892Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-b33f3e08e2e8b3d5aed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-07016cc3ecca7d5e323bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified57.274 +/- 80.719 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB01709
Phenol Explorer Compound IDNot Available
FooDB IDFDB001407
KNApSAcK IDC00000123
Chemspider ID388411
KEGG Compound IDC00631
BioCyc ID2-PG
BiGG ID35542
Wikipedia LinkNot Available
METLIN ID6915
PubChem Compound439278
PDB IDNot Available
ChEBI ID17835
Food Biomarker OntologyNot Available
VMH ID2PG
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
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
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
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
Reactions
2-Phospho-D-glyceric acid → 3-Phosphoglyceric aciddetails
General function:
Involved in magnesium ion binding
Specific function:
Appears to have a function in striated muscle development and regeneration.
Gene Name:
ENO3
Uniprot ID:
P13929
Molecular weight:
42248.03
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails
General function:
Involved in magnesium ion binding
Specific function:
Has neurotrophic and neuroprotective properties on a broad spectrum of central nervous system (CNS) neurons. Binds, in a calcium-dependent manner, to cultured neocortical neurons and promotes cell survival (By similarity).
Gene Name:
ENO2
Uniprot ID:
P09104
Molecular weight:
47268.125
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails
General function:
Involved in magnesium ion binding
Specific function:
Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production. MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
Gene Name:
ENO1
Uniprot ID:
P06733
Molecular weight:
36927.84
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails
General function:
Involved in acid phosphatase activity
Specific function:
Acts as a phosphoinositide 5- and phosphoinositide 6-phosphatase and regulates cellular levels of inositol pentakisphosphate (InsP5) and inositol hexakisphosphate (InsP6). Also acts as a 2,3-bisphosphoglycerate 3-phosphatase, by mediating the dephosphorylation of 2,3-bisphosphoglycerate (2,3-BPG) to produce phospho-D-glycerate without formation of 3-phosphoglycerate. May play a role in bone development (endochondral ossification).
Gene Name:
MINPP1
Uniprot ID:
Q9UNW1
Molecular weight:
34660.555
Reactions
2,3-Diphosphoglyceric acid + Water → 2-Phospho-D-glyceric acid + Phosphatedetails