Human Metabolome Database Version 3.5

Showing metabocard for 2,3-Diphosphoglyceric acid (HMDB01294)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:15 -0700
HMDB ID HMDB01294
Secondary Accession Numbers None
Metabolite Identification
Common Name 2,3-Diphosphoglyceric acid
Description 2,3-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C3H8O10P2
Average Molecular Weight 266.0371
Monoisotopic Molecular Weight 265.9592695
IUPAC Name (2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional IUPAC Name (2R)-2,3-bis(phosphonooxy)propanoic acid
CAS Registry Number 138-81-8
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 Key XOHUEYCVLUUEJJ-UWTATZPHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class N/A
Other Descriptors
  • 2,3-bisphosphoglyceric acid(ChEBI)
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct Parent Sugar Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 9.69 g/L ALOGPS
LogP -1.55 ALOGPS
LogP -1.8 ChemAxon
LogS -1.44 ALOGPS
pKa (strongest acidic) 0.48 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 170.82 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 42.13 ChemAxon
Polarizability 17.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -5 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Testes
  • Erythrocyte
  • Myelin
  • Nerve Cells
  • Reticulocyte
  • Red Blood Cell
Pathways
Name SMPDB Link KEGG Link
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
530.0 +/- 800.0 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Cellular Cytoplasm Detected and Quantified
4500.0 (4000.0-5000.0) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022538
KNApSAcK ID Not Available
Chemspider ID 161681 Link_out
KEGG Compound ID C01159 Link_out
BioCyc ID 23-DIPHOSPHOGLYCERATE Link_out
BiGG ID 1315507 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01294 Link_out
Metagene Link HMDB01294 Link_out
METLIN ID 153 Link_out
PubChem Compound 186004 Link_out
PDB ID DG2 Link_out
ChEBI ID 17720 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Bisphosphoglycerate mutase
Reactions:
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric acid details
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric acid details
Gene Name: BPGM
Uniprot ID: P07738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase 2
Reactions:
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric acid details
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric acid details
Gene Name: PGAM2
Uniprot ID: P15259 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phosphoglycerate mutase 4
Reactions:
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric acid details
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric acid details
Gene Name: PGAM4
Uniprot ID: Q8N0Y7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglycerate mutase 1
Reactions:
Glyceric acid 1,3-biphosphate unknown 2,3-Diphosphoglyceric acid details
2,3-Diphosphoglyceric acid + Water unknown 3-Phosphoglyceric acid + Phosphoric acid details
Gene Name: PGAM1
Uniprot ID: P18669 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Multiple inositol polyphosphate phosphatase 1
Reactions:
2,3-Diphosphoglyceric acid + Water unknown 2-Phospho-D-glyceric acid + Phosphoric acid details
Gene Name: MINPP1
Uniprot ID: Q9UNW1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA