You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00671
Name2,3-bisphospho-D-glyceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2,3-Diphosphoglyceric acid, also known as 2,3-disphospho-D-glycerate or DPG, 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. 2,3-Diphosphoglyceric acid is an extremely strong acidic compound (based on its pKa). 2,3-Diphosphoglyceric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (2R)-2,3-bis(phosphonooxy)-Propanoate
  • (2R)-2,3-bis(phosphonooxy)-Propanoic acid
  • (R)-2,3-bis(phosphonooxy)-Propanoate
  • (R)-2,3-bis(phosphonooxy)-Propanoic acid
  • 2,3-bis(phosphonooxy)-Propanoate
  • 2,3-bis(phosphonooxy)-Propanoic acid
  • 2,3-bisphospho-d-glycerate
  • 2,3-bisphospho-D-glyceric acid
  • 2,3-Bisphosphoglyceric acid
  • 2,3-Diphospho-D-glycerate
  • 2,3-Diphospho-D-glyceric acid
  • 2,3-Diphospho-D-glyceric acid pentasodium salt
  • 2,3-disphospho-D-glycerate
  • 3-phospho-d-glycerol phosphate
  • D-Glyceric acid bis
  • D-Glyceric acid bis(dihydrogen phosphate)
  • d-greenwald ester
  • Diphosphoglycerate
  • Diphosphoglyceric acid
  • DPG
  • Glycerate 2,3-diphosphate
  • Glyceric acid bis(dihydrogen phosphate)
  • Glyceric acid diphosphate
  • 2,3-BPG
  • 2,3-Bisphosphoglycerate
  • 2,3-Disphospho-D-glyceric acid
  • Glycerate bis(dihydrogen phosphate)
  • Glyceric acid bis(dihydrogen phosphoric acid)
  • Glycerate diphosphate
  • Glyceric acid diphosphoric acid
  • 2,3-Diphosphoglycerate
  • 2,3 Diphosphoglyceric acid
  • 2,3 Bisphosphoglycerate
  • 2,3 Diphosphoglycerate
  • 2,3-DPG
  • 2,3-Diphosphoglycerate, (D)-isomer
  • Glycerate 2,3-bisphosphate
  • 2,3-Bisphosphate, glycerate
  • (2R)-2,3-Bis(phosphonooxy)propanoic acid
  • (2R)-2,3-Bis(phosphonooxy)propionic acid
  • 2,3-Bis(phosphonooxy)propanoic acid
  • 2,3-Bis(phosphonooxy)propionic acid
  • 2,3-Diphosphoglyceric acid
  • 2,3-Diphosphonooxypropanoic acid
  • 2,3-Diphosphonooxypropionic acid
CAS number138-81-8
WeightAverage: 266.0371
Monoisotopic: 265.9592695
InChI KeyXOHUEYCVLUUEJJ-UWTATZPHSA-N
InChIInChI=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
IUPAC Name(2R)-2,3-bis(phosphonooxy)propanoic acid
Traditional IUPAC Namediphosphoglycerate
Chemical FormulaC3H8O10P2
SMILESOC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability17.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
SMPDB Reactions
Glyceric acid 1,3-biphosphate2,3-bisphospho-D-glyceric acid
2,3-bisphospho-D-glyceric acid + water3-Phosphoglyceric acid + phosphate
2,3-bisphospho-D-glyceric acid + water3-Phosphoglyceric acid + phosphate
KEGG Reactions
3-phospho-D-glyceroyl dihydrogen phosphate2,3-bisphospho-D-glyceric acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9320000000-fbd8c78fd88d592fab56JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9410000000-ea4c253779009c08e1bdJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0930000000-5127f7f7568a961a8078JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-e9e3c8a32ece4b7f9fceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006t-9300000000-e09861cf36df495519f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0090000000-4a9ded352d5912810741JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-066r-1960000000-0d244402e55e5ef9de1dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9330000000-70ae76c58e470fe3b594JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-6cacbc2756ef980dc5a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00xr-6910000000-871a376b75658c914a1eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xr-9200000000-ab1b55ce1ad971f1b3f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-016r-9100000000-2af5a77daca9f7cef852JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9100000000-1d6a9786ab78002b7ac2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4a9ded352d5912810741JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-1960000000-fcab8021959f67dc5a44JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ar0-5960000000-1d5a4352115c6c5eb82fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9330000000-70ae76c58e470fe3b594JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-37f228e9721638e33212JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uxr-1490000000-ddf502cfcfd4ff0bca0bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1930000000-6b2743652b0e2aa81960JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-8890000000-64b460dbcc7be6d3e820JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-7cbb7d86341bbdc1500aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-5090000000-73e5bca24796a45bebafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-a07defbdfd47a3f23225JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9f9abb79cd423f7b15f0JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID37527
HMDB IDHMDB01294
Pubchem Compound ID186004
Kegg IDC01159
ChemSpider ID161681
FOODB IDFDB022538
Wikipedia ID2,3-Bisphosphoglyceric acid
BioCyc ID23-DIPHOSPHOGLYCERATE

Enzymes

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:
GPM1
Uniprot ID:
P00950
Molecular weight:
27608.30078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Involved, either directly or indirectly, in the bidirectional transport of sterols between the endoplasmic reticulum and the plasma membrane
Gene Name:
DET1
Uniprot ID:
Q99288
Molecular weight:
39171.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:
Not Available
Uniprot ID:
Q12040
Molecular weight:
26176.5
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM3
Uniprot ID:
Q12326
Molecular weight:
34863.19922
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM2
Uniprot ID:
Q12008
Molecular weight:
36072.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.