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2,3-bisphospho-D-glyceric acid (YMDB00671)

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
MOLSDFPDBSMILESInChI
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-biphosphate ↔ 2,3-bisphospho-D-glyceric acid
2,3-bisphospho-D-glyceric acid + water ↔ 3-Phosphoglyceric acid + phosphate
2,3-bisphospho-D-glyceric acid + water ↔ 3-Phosphoglyceric acid + phosphate
KEGG Reactions
3-phospho-D-glyceroyl dihydrogen phosphate ↔ 2,3-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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Phosphoglycerate mutase 1
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.
Protein Details
2. Putative phosphoglycerate mutase DET1
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.
Protein Details
3. Probable phosphoglycerate mutase YOR283W
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.
Protein Details
4. Phosphoglycerate mutase 3
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.
Protein Details
5. Phosphoglycerate mutase 2
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.