Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:15 UTC
HMDB IDHMDB01294
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Diphosphoglyceric acid
Description2,3-Bisphosphoglycerate (2,3-BPG, also known as 2,3-diphosphoglycerate or 2,3-DPG) 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
  1. (2R)-2,3-bis(phosphonooxy)-Propanoate
  2. (2R)-2,3-bis(phosphonooxy)-Propanoic acid
  3. (R)-2,3-bis(phosphonooxy)-Propanoate
  4. (R)-2,3-bis(phosphonooxy)-Propanoic acid
  5. 2,3-Bis(phosphonooxy)-Propanoate
  6. 2,3-Bis(phosphonooxy)-Propanoic acid
  7. 2,3-Bisphospho-D-glycerate
  8. 2,3-Bisphospho-D-glyceric acid
  9. 2,3-Bisphosphoglyceric acid
  10. 2,3-Diphospho-D-glycerate
  11. 2,3-Diphospho-D-glyceric acid
  12. 2,3-Diphospho-D-glyceric acid pentasodium salt
  13. 2,3-Disphospho-D-glycerate
  14. D-Glyceric acid bis
  15. D-Glyceric acid bis(dihydrogen phosphate)
  16. Diphosphoglycerate
  17. Diphosphoglyceric acid
  18. Glycerate 2,3-diphosphate
  19. Glyceric acid bis(dihydrogen phosphate)
  20. Glyceric acid diphosphate
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
CAS Registry Number138-81-8
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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassN/A
Other Descriptors
  • 2,3-bisphosphoglyceric acid(ChEBI)
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct ParentSugar Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 solubility9.69 g/LALOGPS
logP-1.6ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (strongest acidic)0.48ChemAxon
physiological charge-5ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count5ChemAxon
polar surface area170.82ChemAxon
rotatable bond count6ChemAxon
refractivity42.13ChemAxon
polarizability17.96ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Erythrocyte
  • Myelin
  • Nerve Cells
  • Red Blood Cell
  • Reticulocyte
  • Testes
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified530.0 +/- 800.0 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified4500.0 (4000.0-5000.0) uMAdult (>18 years old)BothNormal
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 IDFDB022538
KNApSAcK IDNot Available
Chemspider ID161681
KEGG Compound IDC01159
BioCyc ID23-DIPHOSPHOGLYCERATE
BiGG ID1315507
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01294
Metagene LinkHMDB01294
METLIN ID153
PubChem Compound186004
PDB IDDG2
ChEBI ID17720
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. Pubmed: 15882454
  2. Mairbaurl H, Schobersberger W, Oelz O, Bartsch P, Eckardt KU, Bauer C: Unchanged in vivo P50 at high altitude despite decreased erythrocyte age and elevated 2,3-diphosphoglycerate. J Appl Physiol. 1990 Mar;68(3):1186-94. Pubmed: 2111310
  3. Luganova IS, Blinov MN, Abdulkadyrova AS: [Age composition of the erythrocyte population, ATP and 2,3-diphosphoglycerate composition in erythrocytes in different forms of hemolytic anemia] Vopr Med Khim. 1978 Jul-Aug;24(4):499-505. Pubmed: 685194
  4. Miwa S, Fujii H, Matsumoto N, Nakatsuji T, Oda S, Asano H, Asano S: A case of red-cell adenosine deaminase overproduction associated with hereditary hemolytic anemia found in Japan. Am J Hematol. 1978;5(2):107-15. Pubmed: 736030
  5. Sezdi M, Bayik M, Ulgen Y: Storage effects on the Cole-Cole parameters of erythrocyte suspensions. Physiol Meas. 2006 Jul;27(7):623-35. Epub 2006 Apr 28. Pubmed: 16705260
  6. Linko K, Hekali R: Influence of the Taurus radiowave blood warmer on human red cells. Hemolysis and erythrocyte ATP and 2,3 DPG concentrations following warming by radiowaves, microwaves and water bath. Acta Anaesthesiol Scand. 1980;24(1):46-52. Pubmed: 7376803
  7. Shanoian SA, Gel'shtein GG, Sharova IuA, Metina RA, Lifliandskii DB: [Study of 2,3-diphosphoglyceric acid levels in artificial blood circulation with the use of a perfusate composed of defrosted erythrocytes and donor blood] Probl Gematol Pereliv Krovi. 1976 Feb;21(2):41-3. Pubmed: 1257232
  8. Spodaryk K, Zoladz JA: The 2,3-DPG levels of human red blood cells during an incremental exercise test: relationship to the blood acid-base balance. Physiol Res. 1998;47(1):17-22. Pubmed: 9708696
  9. Springer RR, Clark DK, Lea AS, Solis RT: Effects of changes in arterial carbon dioxide tension on oxygen consumption during cardiopulmonary bypass. Chest. 1979 May;75(5):549-54. Pubmed: 35315
  10. Coppola L, Giunta R, Verrazzo G, Luongo C, Sammartino A, Vicario C, Giugliano D: Influence of ozone on haemoglobin oxygen affinity in type-2 diabetic patients with peripheral vascular disease: in vitro studies. Diabete Metab. 1995 Oct;21(4):252-5. Pubmed: 8529759
  11. Nakano T, Fujioka H, Tamura S, Amuro Y, Nabeshima K, Hada T, Higashino K: Erythrocyte 2,3-diphosphoglycerate in liver diseases. Am J Gastroenterol. 1987 Dec;82(12):1283-6. Pubmed: 2825516
  12. diBella G, Scandariato G, Suriano O, Rizzo A: Oxygen affinity and Bohr effect responses to 2,3-diphosphoglycerate in equine and human blood. Res Vet Sci. 1996 May;60(3):272-5. Pubmed: 8735521
  13. Pas'ko SA, Volosheniuk TG: [Causes, sequelae and possible ways of preventing hypophosphatemia in patients with cerebral ischemia] Zh Nevropatol Psikhiatr Im S S Korsakova. 1990;90(10):25-7. Pubmed: 1962992
  14. Rosenmund A, Binswanger U, Straub PW: Oxidative injury to erythrocytes, cell rigidity, and splenic hemolysis in hemodialyzed uremic patients. Ann Intern Med. 1975 Apr;82(4):460-5. Pubmed: 1119763
  15. Antonowicz J, Andrzejak R, Smolik R: Influence of heavy metal mixtures on erythrocyte metabolism. Int Arch Occup Environ Health. 1990;62(3):195-8. Pubmed: 2347640
  16. Krasomski G, Zachara B: [2,3-diphosphoglycerate level in the red blood cells, inorganic phosphorus in the blood serum and the acid-base equilibrium indicators in different periods of normal pregnancy] Ginekol Pol. 1981 Aug;52(8):687-92. Pubmed: 7308813
  17. Wallas CH: Elevated red blood cell 2,3-diphosphoglycerate levels in black blood donors. Transfusion. 1978 Jan-Feb;18(1):108-12. Pubmed: 625775
  18. Hirszel P, Maher JF, Tempel GE, Mengel CE: Effect of hemodialysis on factors influencing oxygen transport. J Lab Clin Med. 1975 Jun;85(6):978-86. Pubmed: 237054
  19. Lijnen P, Hespel P, Van Oppens S, Fiocchi R, Goossens W, Vanden Eynde E, Amery A: Erythrocyte 2,3-diphosphoglycerate and serum enzyme concentrations in trained and sedentary men. Med Sci Sports Exerc. 1986 Apr;18(2):174-9. Pubmed: 3702645
  20. Yoneda S, Kako T, Kohketsu M, Fujinami T: Changes in blood viscosity following nifedipine administration and its relation to the contents of adenosine triphosphate and 2,3-diphosphoglyceric acid in red blood cells in patients with angina pectoris. Arzneimittelforschung. 1989 Apr;39(4):504-6. Pubmed: 2751737

Enzymes

Gene Name:
BPGM
Uniprot ID:
P07738
Reactions
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric aciddetails
Gene Name:
PGAM2
Uniprot ID:
P15259
Reactions
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric aciddetails
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Reactions
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric aciddetails
Gene Name:
PGAM1
Uniprot ID:
P18669
Reactions
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric aciddetails
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric aciddetails
Gene Name:
MINPP1
Uniprot ID:
Q9UNW1
Reactions
2,3-Diphosphoglyceric acid + Water unknown 2-Phospho-D-glyceric acid + Phosphoric aciddetails