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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
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.