Chemicals and Drugs

2,3-Diphosphoglycerate

A highly anionic organic phosphate which is present in human red blood cells at about the same molar ratio as hemoglobin. It binds to deoxyhemoglobin but not the oxygenated form, therefore diminishing the oxygen affinity of hemoglobin. This is essential in enabling hemoglobin to unload oxygen in tissue capillaries. It is also an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate by phosphoglycerate mutase (EC 5.4.2.1). (From Stryer Biochemistry, 4th ed, p160; Enzyme Nomenclature, 1992, p508)

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A highly anionic organic phosphate which is present in human red blood cells at about the same molar ratio as hemoglobin. It binds to deoxyhemoglobin but not the oxygenated form, therefore diminishing the oxygen affinity of hemoglobin. This is essential in enabling hemoglobin to unload oxygen in tissue capillaries. It is also an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate by phosphoglycerate mutase (EC 5.4.2.1). (From Stryer Biochemistry, 4th ed, p160; Enzyme Nomenclature, 1992, p508)

Chemical Identity

Chemical Information

Molecular Formula
C3H8O10P2
Molecular Weight
266.04 g/mol
CAS Registry No.
138-81-8
IUPAC Name
2,3-diphosphonooxypropanoic acid
InChIKey
XOHUEYCVLUUEJJ-UHFFFAOYSA-N
SMILES
C(C(C(=O)O)OP(=O)(O)O)OP(=O)(O)O
MeSH Unique ID
D019794
Source
PubChem CID 61

MeSH Record

Classification

Broader headings

Related Concepts

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MeSH Record

Synonyms

9 entry terms
  • 2,3-Bisphosphoglycerate
  • 2,3-DPG
  • Glycerate 2,3-Bisphosphate
  • 2,3 Bisphosphoglycerate
  • 2,3 Diphosphoglycerate
  • 2,3-Bisphosphate, Glycerate
  • 2,3-Diphosphoglycerate, (D)-Isomer
  • 2,3-Diphosphoglyceric Acid
  • 2,3 Diphosphoglyceric Acid

MeSH Record

Aspects Covered

24 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

98; use 2,3-DIPHOSPHOGLYCERATE (NM) 1980-97

MeSH Record

Previous Indexing

  • Diphosphoglyceric Acids (1980-1997)

MeSH Hierarchy

Tree Numbers

  1. D02w.241w.081.844w.387w.388w.175w
  2. D02w.241w.511w.902w.387w.388w.175w
  3. D02w.705w.400w.140w.175w
  4. D09w.811w.366w.388w.175w

AMA Style

References

  1. National Library of Medicine. 2,3-Diphosphoglycerate. Medical Subject Headings (MeSH). 2026. Unique ID D019794. http://id.nlm.nih.gov/mesh/2026/D019794
  2. 2,3-Diphosphoglycerate. In: Wikipedia. https://en.wikipedia.org/wiki/2,3-Bisphosphoglyceric_acid
  3. 2,3-Diphosphoglycerate. In: Wikidata. https://www.wikidata.org/wiki/Q209155
  4. 2,3-Diphosphoglycerate. In: PubChem Compound. CID 61. https://pubchem.ncbi.nlm.nih.gov/compound/61