Identification
YMDB IDYMDB00270
NameGlyceric acid 1,3-biphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1,3-Bisphosphoglycerate (1,3BPG) is a 3-carbon organic molecule present in most, if not all, living organisms. It primarily exists as a metabolic intermediate in both glycolysis during respiration and the Calvin cycle during photosynthesis. 1,3BPG is a transitional stage between glycerate 3-phosphate and glyceraldehyde 3-phosphate during the fixation/reduction of CO2. 1,3BPG is also a precursor to 2,3-bisphosphoglycerate which in turn is a reaction intermediate in the glycolytic pathway.
Structure
Thumb
Synonyms
  • 1,3-Biphosphoglycerate
  • 1,3-Biphosphoglyceric acid
  • 1,3-bis-phosphoglycerate
  • 1,3-Bisphosphoglycerate
  • 1,3-diphosphateglycerate
  • 1,3-Diphosphoglycerate
  • 13-DPG
  • 2-hydroxy-3-(phosphonooxy)-Propanoate
  • 2-hydroxy-3-(phosphonooxy)-Propanoic acid
  • 2-hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphorate
  • 2-hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphoric acid
  • 3-P-glyceroyl-P
  • 3-Phospho-D-glyceroyl phosphate
  • 3-phospho-D-glyceroyl-phosphate
  • 3-Phosphoglyceroyl phosphate
  • 3-phosphoglyceroyl-P
  • 3-phosphoglyceroyl-phosphate
  • DPG
  • Glycerate 1,3-Biphosphate
  • glycerate 1,3-bisphosphate
  • glycerate 1,3-diphosphate
  • Glyceric acid 1,3-biphosphate
  • Glyceric acid 1,3-biphosphic acid
  • P-glyceroyl-P
  • Phosphoglyceroyl-P
  • Glyceric acid 1,3-biphosphoric acid
CAS number1981-49-3
WeightAverage: 266.0371
Monoisotopic: 265.9592695
InChI KeyLJQLQCAXBUHEAZ-UHFFFAOYSA-N
InChIInChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
IUPAC Name{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional IUPAC Name1,3-bisphosphoglycerate
Chemical FormulaC3H8O10P2
SMILES[H]OC([H])(C(=O)OP(=O)(O[H])O[H])C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Glyceric_acid
  • Monoalkyl phosphate
  • Monosaccharide
  • Alkyl phosphate
  • Carboxylic acid salt
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.64 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
D-Glyceraldehyde 3-phosphate + NAD + Phosphoric acidGlyceric acid 1,3-biphosphate + NADH
Glyceric acid 1,3-biphosphate2,3-bisphospho-D-glyceric acid
Glyceric acid 1,3-biphosphate + ADP3-Phosphoglyceric acid + Adenosine triphosphate
Glucose 1-phosphate + Glyceric acid 1,3-biphosphateAlpha-D-Glucose 1,6-bisphosphate + 3-Phosphoglyceric acid
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
100 ± 0 µM Minimal medium supplemented with ammonia saltsaerobic;resting cellsBaker's yeastPMID: 4578278
30 ± 0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9230000000-4f86f41b27dd191408b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1950000000-2cde7b5739871a882542JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3910000000-72f2c46eab2036938056JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-c835034f0ac11618922dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6190000000-6f4870543fc6131d14a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d9d9c6d217a255d791fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1fef400a1ea8ca54c802JSpectraViewer
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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB01270
Pubchem Compound ID683
Kegg IDC00236
ChemSpider ID663
FOODB IDFDB022524
Wikipedia1,3-bisphosphoglycerate
BioCyc IDDPG

Enzymes

General function:
Involved in phosphoglycerate kinase activity
Specific function:
ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:
PGK1
Uniprot ID:
P00560
Molecular weight:
44738.0
Reactions
ATP + 3-phospho-D-glycerate → ADP + 3-phospho-D-glyceroyl phosphate.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH1
Uniprot ID:
P00360
Molecular weight:
35749.60156
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH2
Uniprot ID:
P00358
Molecular weight:
35846.60156
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH3
Uniprot ID:
P00359
Molecular weight:
35746.39844
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
Not Available
Uniprot ID:
Q03262
Molecular weight:
71068.60156
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
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.