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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:10 UTC
HMDB IDHMDB0001294
Secondary Accession Numbers
  • HMDB01294
Metabolite Identification
Common Name2,3-Diphosphoglyceric acid
Description2,3-Bisphosphoglycerate (CAS: 138-81-8), also known as 2,3-BPG or 2,3-diphosphoglycerate, is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte) at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch.
Structure
Thumb
Synonyms
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional Namediphosphoglycerate
CAS Registry Number14438-19-8
SMILES
OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1
InChI KeyXOHUEYCVLUUEJJ-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
  • Monoalkyl phosphate
  • Glyceric_acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue Locations
  • Erythrocyte
  • Neuron
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified530.0 +/- 800.0 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified4500.0 (4000.0-5000.0) 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 IDFDB022538
KNApSAcK IDNot Available
Chemspider ID161681
KEGG Compound IDC01159
BioCyc ID23-DIPHOSPHOGLYCERATE
BiGG ID1315507
Wikipedia Link2,3-Bisphosphoglyceric acid
METLIN ID153
PubChem Compound186004
PDB IDNot Available
ChEBI ID17720
Food Biomarker OntologyNot Available
VMH ID23DPG
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphatedetails
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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphatedetails
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
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Phosphatedetails
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