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Record Information
Version	2.0
Creation Date	2012-05-31 13:48:45 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01270
Identification
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.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa856086c> Close
Synonyms:	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
Weight:	Average: 266.0371 Monoisotopic: 265.9592695
InChI Key:	LJQLQCAXBUHEAZ-UHFFFAOYSA-N
InChI:	InChI=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)
CAS number:	1981-49-3
IUPAC Name:	{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional IUPAC Name:	1,3-bisphosphoglycerate
SMILES:	OC(COP(O)(O)=O)C(=O)OP(O)(O)=O
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Organic phosphoric acids and derivatives
Sub Class	Phosphate esters
Direct Parent	Acyl monophosphates
Alternative Parents	Sugar acids and derivatives Monoalkyl phosphates Monosaccharides Secondary alcohols Carboxylic acid salts Monocarboxylic acids and derivatives Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 9.64 g/L ALOGPS logP -1.1 ALOGPS logP -2.3 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.01 ChemAxon pKa (Strongest Basic) -4.2 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 170.82 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 42.42 m³·mol⁻¹ ChemAxon Polarizability 18.04 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	D-Glyceraldehyde 3-phosphate + NAD + Phosphate <> Glyceric acid 1,3-biphosphate + Hydrogen ion + NADH + 3-phospho-D-glyceroyl phosphate 3-Phosphoglycerate + Adenosine triphosphate <> Glyceric acid 1,3-biphosphate + ADP D-Glyceraldehyde 3-phosphate + Phosphate + NAD <> Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion Adenosine triphosphate + 3-Phospho-D-glycerate <> ADP + Glyceric acid 1,3-biphosphate + 3-phospho-D-glyceroyl phosphate Glyceric acid 1,3-biphosphate + Water <> 3-Phospho-D-glycerate + Phosphate D-Glyceraldehyde 3-phosphate + NAD + Phosphate + D-Glyceraldehyde 3-phosphate > Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion + Glyceric acid 1,3-biphosphate Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion + Glyceric acid 1,3-biphosphate > NAD + Phosphate + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate Glyceric acid 1,3-biphosphate + Adenosine diphosphate + Glyceric acid 1,3-biphosphate + ADP > Adenosine triphosphate + 3-Phosphoglyceric acid + 3-Phosphoglycerate 3-Phosphoglyceric acid + Adenosine triphosphate + 3-Phosphoglycerate > Adenosine diphosphate + Glyceric acid 1,3-biphosphate + ADP + Glyceric acid 1,3-biphosphate Adenosine triphosphate + 3 3-Phospho-D-glycerate <> ADP + Glyceric acid 1,3-biphosphate +3 3-phospho-D-glyceroyl phosphate Adenosine triphosphate + 3 3-Phospho-D-glycerate <> ADP + Glyceric acid 1,3-biphosphate +3 3-phospho-D-glyceroyl phosphate
SMPDB Pathways:	Gluconeogenesis from L-malic acid PW000819 fructose metabolism PW000913 glycerol metabolism PW000914 glycerol metabolism II PW000915 glycerol metabolism III (sn-glycero-3-phosphoethanolamine) PW000916 glycerol metabolism IV (glycerophosphoglycerol) PW000917 glycerol metabolism V (glycerophosphoserine) PW000918 glycolysis and pyruvate dehydrogenase PW000785
KEGG Pathways:	Glycolysis / Gluconeogenesis ec00010 Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:	gluconeogenesis I GLUCONEO-PWY glycolysis I GLYCOLYSIS
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9500000000-cb3071f9249ee92b7d2c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-0002-9230000000-4f86f41b27dd191408b9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-1950000000-2cde7b5739871a882542 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014m-3910000000-72f2c46eab2036938056 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000f-9500000000-c835034f0ac11618922d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03fr-6190000000-6f4870543fc6131d14a7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-d9d9c6d217a255d791fd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-1fef400a1ea8ca54c802 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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)
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID HMDB01270 Pubchem Compound ID 683 Kegg ID Not Available ChemSpider ID 663 Wikipedia 1,3-Biphosphoglycerate BioCyc ID DPG EcoCyc ID DPG

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