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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
Data?1584462030
Synonyms
ValueSource
2,3-Bisphospho-D-glycerateChEBI
2,3-Bisphosphoglyceric acidChEBI
2,3-BPGChEBI
2,3-Disphospho-D-glycerateChEBI
D-Greenwald esterChEBI
DPGChEBI
Glyceric acid bis(dihydrogen phosphate)ChEBI
Glyceric acid diphosphateChEBI
2,3-Bisphospho-D-glyceric acidGenerator
2,3-BisphosphoglycerateGenerator
2,3-Disphospho-D-glyceric acidGenerator
Glycerate bis(dihydrogen phosphate)Generator
Glyceric acid bis(dihydrogen phosphoric acid)Generator
Glycerate diphosphateGenerator
Glyceric acid diphosphoric acidGenerator
2,3-DiphosphoglycerateGenerator
(2R)-2,3-Bis(phosphonooxy)-propanoateHMDB
(2R)-2,3-Bis(phosphonooxy)-propanoic acidHMDB
(R)-2,3-Bis(phosphonooxy)-propanoateHMDB
(R)-2,3-Bis(phosphonooxy)-propanoic acidHMDB
2,3-Bis(phosphonooxy)-propanoateHMDB
2,3-Bis(phosphonooxy)-propanoic acidHMDB
2,3-Diphospho-D-glycerateHMDB
2,3-Diphospho-D-glyceric acidHMDB
2,3-Diphospho-D-glyceric acid pentasodium saltHMDB
D-Glyceric acid bisHMDB
D-Glyceric acid bis(dihydrogen phosphate)HMDB
DiphosphoglycerateHMDB
Diphosphoglyceric acidHMDB
Glycerate 2,3-diphosphateHMDB
2,3 Diphosphoglyceric acidHMDB
2,3 BisphosphoglycerateHMDB
2,3 DiphosphoglycerateHMDB
2,3-DPGHMDB
2,3-Diphosphoglycerate, (D)-isomerHMDB
Glycerate 2,3-bisphosphateHMDB
2,3-Bisphosphate, glycerateHMDB
(2R)-2,3-Bis(phosphonooxy)propanoic acidHMDB
(2R)-2,3-Bis(phosphonooxy)propionic acidHMDB
2,3-Bis(phosphonooxy)propanoic acidHMDB
2,3-Bis(phosphonooxy)propionic acidHMDB
2,3-Diphosphoglyceric acidHMDB
2,3-Diphosphonooxypropanoic acidHMDB
2,3-Diphosphonooxypropionic acidHMDB
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
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 Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability17.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.49531661259
DarkChem[M-H]-151.98931661259
AllCCS[M+H]+154.74332859911
AllCCS[M-H]-141.82432859911
DeepCCS[M+H]+131.47230932474
DeepCCS[M-H]-129.07830932474
DeepCCS[M-2H]-162.69830932474
DeepCCS[M+Na]+137.38430932474
AllCCS[M+H]+154.732859911
AllCCS[M+H-H2O]+151.432859911
AllCCS[M+NH4]+157.832859911
AllCCS[M+Na]+158.732859911
AllCCS[M-H]-141.832859911
AllCCS[M+Na-2H]-142.732859911
AllCCS[M+HCOO]-143.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-Diphosphoglyceric acidOC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O2694.5Standard polar33892256
2,3-Diphosphoglyceric acidOC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O1779.9Standard non polar33892256
2,3-Diphosphoglyceric acidOC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O2341.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Diphosphoglyceric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O2071.0Semi standard non polar33892256
2,3-Diphosphoglyceric acid,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O)C(=O)O2139.7Semi standard non polar33892256
2,3-Diphosphoglyceric acid,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O)O)C(=O)O2135.5Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O2097.1Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O2142.3Standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O3324.0Standard polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C2083.8Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C2149.9Standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C3355.6Standard polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C2133.6Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C2190.8Standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C3124.0Standard polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C)C(=O)O2192.2Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C)C(=O)O2150.6Standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C)C(=O)O3126.2Standard polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #5C[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C2112.8Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #5C[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C2215.1Standard non polar33892256
2,3-Diphosphoglyceric acid,2TMS,isomer #5C[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C3173.7Standard polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O2129.7Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O2189.9Standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O2931.7Standard polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2137.0Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2149.5Standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2958.3Standard polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2120.6Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2208.5Standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2975.7Standard polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2208.3Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2177.1Standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2808.5Standard polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2203.0Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2190.2Standard non polar33892256
2,3-Diphosphoglyceric acid,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2825.1Standard polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2182.1Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2196.5Standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2686.4Standard polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2181.7Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2208.5Standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2706.4Standard polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C2245.9Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C2225.6Standard non polar33892256
2,3-Diphosphoglyceric acid,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C2593.0Standard polar33892256
2,3-Diphosphoglyceric acid,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2226.1Semi standard non polar33892256
2,3-Diphosphoglyceric acid,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2222.9Standard non polar33892256
2,3-Diphosphoglyceric acid,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2490.5Standard polar33892256
2,3-Diphosphoglyceric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O2324.5Semi standard non polar33892256
2,3-Diphosphoglyceric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O)C(=O)O2385.6Semi standard non polar33892256
2,3-Diphosphoglyceric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O)O)C(=O)O2376.0Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2535.7Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2591.8Standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3441.2Standard polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2512.5Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2589.7Standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3469.1Standard polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C2575.0Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C2570.6Standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C3296.6Standard polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2608.7Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2567.3Standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O3271.5Standard polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C2531.3Semi standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C2603.4Standard non polar33892256
2,3-Diphosphoglyceric acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O[C@H](COP(=O)(O)O)C(=O)O)O[Si](C)(C)C(C)(C)C3342.3Standard polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2775.9Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2745.1Standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3143.5Standard polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2786.5Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2754.0Standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3144.1Standard polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2742.2Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2761.4Standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3182.0Standard polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2831.3Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2697.8Standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O3030.5Standard polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2815.8Semi standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2713.9Standard non polar33892256
2,3-Diphosphoglyceric acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O3042.5Standard polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3014.3Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2855.7Standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2965.4Standard polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3003.8Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2871.0Standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2983.3Standard polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C3047.8Semi standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C2799.8Standard non polar33892256
2,3-Diphosphoglyceric acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C2903.0Standard polar33892256
2,3-Diphosphoglyceric acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3228.6Semi standard non polar33892256
2,3-Diphosphoglyceric acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2963.0Standard non polar33892256
2,3-Diphosphoglyceric acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2902.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Diphosphoglyceric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9320000000-fbd8c78fd88d592fab562016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Diphosphoglyceric acid GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9410000000-ea4c253779009c08e1bd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Diphosphoglyceric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-0930000000-5127f7f7568a961a80782012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-2900000000-e9e3c8a32ece4b7f9fce2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-006t-9300000000-e09861cf36df495519f62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0090000000-4a9ded352d59128107412012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-066r-1960000000-0d244402e55e5ef9de1d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0ar0-5960000000-1d5a4352115c6c5eb82f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-056r-9330000000-70ae76c58e470fe3b5942012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9100000000-6cacbc2756ef980dc5a22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00xr-6910000000-871a376b75658c914a1e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00xr-9200000000-ab1b55ce1ad971f1b3f82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-016r-9100000000-2af5a77daca9f7cef8522012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-9100000000-1d6a9786ab78002b7ac22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , negative-QTOFsplash10-014i-0090000000-4a9ded352d59128107412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , negative-QTOFsplash10-066r-1960000000-fcab8021959f67dc5a442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , negative-QTOFsplash10-0ar0-5960000000-1d5a4352115c6c5eb82f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , negative-QTOFsplash10-056r-9330000000-70ae76c58e470fe3b5942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , negative-QTOFsplash10-004i-9100000000-37f228e9721638e332122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid LC-ESI-QQ , positive-QTOFsplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 10V, Positive-QTOFsplash10-014i-1930000000-6b2743652b0e2aa819602016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 20V, Positive-QTOFsplash10-00r2-8890000000-64b460dbcc7be6d3e8202016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 40V, Positive-QTOFsplash10-00di-6900000000-7cbb7d86341bbdc1500a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 10V, Negative-QTOFsplash10-03fr-5090000000-73e5bca24796a45bebaf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 20V, Negative-QTOFsplash10-004i-9010000000-a07defbdfd47a3f232252016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Diphosphoglyceric acid 40V, Negative-QTOFsplash10-004i-9000000000-9f9abb79cd423f7b15f02016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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)Download (PDF)
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;2:18. [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 (1985). 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

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