Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000317
Name: Glyceric acid 1,3-biphosphate
Description:1,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration.
  • 1,3-Biphosphoglycerate
  • 1,3-Biphosphoglyceric acid
  • 1,3-Bis-phosphoglycerate
  • 1,3-Bis-phosphoglyceric acid
  • 1,3-Bisphosphoglycerate
  • 1,3-Bisphosphoglyceric acid
  • 1,3-Diphosphateglycerate
  • 1,3-Diphosphateglyceric acid
  • 1,3-Diphosphoglycerate
  • 1,3-Diphosphoglyceric acid
  • 1,3-DPG
  • 13-DPG
  • 2-Hydroxy-3-(phosphonooxy)-Propanoate
  • 2-Hydroxy-3-(phosphonooxy)-propanoate 1-anhydride with phosphate
  • 2-Hydroxy-3-(phosphonooxy)-Propanoate 1-anhydride with phosphorate
  • 2-Hydroxy-3-(phosphonooxy)-Propanoate 1-anhydride with phosphoric acid
  • 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 phosphoric acid
  • 3-Phospho-D-glyceroyl-phosphate
  • 3-phospho-D-Glyceroyl-phosphoric acid
  • 3-Phosphoglyceroyl phosphate
  • 3-Phosphoglyceroyl phosphoric acid
  • 3-Phosphoglyceroyl-P
  • 3-Phosphoglyceroyl-phosphate
  • 3-Phosphoglyceroyl-phosphoric acid
  • DPG
  • Glycerate 1,3-Biphosphate
  • Glycerate 1,3-bisphosphate
  • Glycerate 1,3-diphosphate
  • Glyceric acid 1,3-biphosphate
  • Glyceric acid 1,3-biphosphoric acid
  • Glyceric acid 1,3-bisphosphate
  • Glyceric acid 1,3-bisphosphoric acid
  • Glyceric acid 1,3-diphosphate
  • Glyceric acid 1,3-diphosphoric acid
  • P-Glyceroyl-P
  • Phosphoglyceroyl-P
Chemical Formula: C3H8O10P2
Average Molecular Weight: 266.0371
Monoisotopic Molecular Weight: 265.9592695
CAS number: 1981-49-3
IUPAC Name:{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional IUPAC Name: 1,3-bisphosphoglycerate
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct Parent Sugar acids and derivatives
Alternative Parents
  • Monoalkyl phosphate
  • Glyceric_acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility9.64 mg/mLALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m3·mol-1ChemAxon
Polarizability18.04 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
  • Glycolysis / Gluconeogenesis pae00010
  • Microbial metabolism in diverse environments pae01120
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1950000000-2cde7b5739871a882542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3910000000-72f2c46eab2036938056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-c835034f0ac11618922dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6190000000-6f4870543fc6131d14a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d9d9c6d217a255d791fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1fef400a1ea8ca54c802View in MoNA
  • Carreras J, Bartrons R, Climent F, Cusso R: Bisphosphorylated metabolites of glycerate, glucose, and fructose: functions, metabolism and molecular pathology. Clin Biochem. 1986 Dec;19(6):348-58. Pubmed: 3555887
  • Fabry ME, Nagel RL: Heterogeneity of red cells in the sickler: a characteristic with practical clinical and pathophysiological implications. Blood Cells. 1982;8(1):9-15. Pubmed: 7115982
  • Flachner B, Varga A, Szabo J, Barna L, Hajdu I, Gyimesi G, Zavodszky P, Vas M: Substrate-assisted movement of the catalytic Lys 215 during domain closure: site-directed mutagenesis studies of human 3-phosphoglycerate kinase. Biochemistry. 2005 Dec 27;44(51):16853-65. Pubmed: 16363799
  • Fokina KV, Dainyak MB, Nagradova NK, Muronetz VI: A study on the complexes between human erythrocyte enzymes participating in the conversions of 1,3-diphosphoglycerate. Arch Biochem Biophys. 1997 Sep 15;345(2):185-92. Pubmed: 9308888
  • Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8. Pubmed: 8753225
  • Inoue H, Moriyasu M, Hamasaki N: Metabolism of 3-phosphoglyceroyl phosphate in phosphoenolpyruvate-enriched human erythrocytes. J Biol Chem. 1987 Jun 5;262(16):7635-8. Pubmed: 3584133
  • Joao HC, Williams RJ: The anatomy of a kinase and the control of phosphate transfer. Eur J Biochem. 1993 Aug 15;216(1):1-18. Pubmed: 8365395
  • Jovanovic S, Du Q, Crawford RM, Budas GR, Stagljar I, Jovanovic A: Glyceraldehyde 3-phosphate dehydrogenase serves as an accessory protein of the cardiac sarcolemmal K(ATP) channel. EMBO Rep. 2005 Sep;6(9):848-52. Pubmed: 16082386
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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(1):18. Pubmed: 15882454
  • Oimomi M, Yoshimura Y, Kubota S, Tanke G, Takagi K, Baba S: Effect of hydrocortisone on the synthesis of 2,3-diphosphoglycerate in human erythrocytes. Transfusion. 1982 Jul-Aug;22(4):266-8. Pubmed: 7101418
  • Sayed A, Matsuyama S, Inoue K, Alsina J, Cai F, Chen J, Inouye M: ATPase and GTPase activities copurifying with GTP-binding proteins in E. coli. J Mol Microbiol Biotechnol. 2000 Jul;2(3):261-3. Pubmed: 10937433
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
CHEBI IDNot Available
Pubchem Compound ID683
Kegg IDC00236
ChemSpider ID663