Glyceric acid 1,3-biphosphate (ECMDB01270) (M2MDB000317)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (5)
Record Information
Version2.0
Creation Date2012-05-31 13:48:45 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01270
Identification
Name:Glyceric acid 1,3-biphosphate
Description1,3-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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.
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
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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 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 acidPW000819 ThumbThumb?image type=greyscaleThumb?image type=simple
fructose metabolismPW000913 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolismPW000914 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism V (glycerophosphoserine)PW000918 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Glycolysis / Gluconeogenesis ec00010
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9230000000-4f86f41b27dd191408b9View in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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)
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB01270
Pubchem Compound ID683
Kegg IDNot Available
ChemSpider ID663
Wikipedia1,3-Biphosphoglycerate
BioCyc IDDPG
EcoCyc IDDPG

Enzymes

Protein Details
1. Phosphoglycerate kinase
General function:
Involved in phosphoglycerate kinase activity
Specific function:
ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:
pgk
Uniprot ID:
P0A799
Molecular weight:
41118
Reactions
ATP + 3-phospho-D-glycerate = ADP + 3-phospho-D-glyceroyl phosphate.
Protein Details
2. Glyceraldehyde-3-phosphate dehydrogenase A
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:
gapA
Uniprot ID:
P0A9B2
Molecular weight:
35532
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH.
Protein Details
3. Acylphosphatase
General function:
Involved in acylphosphatase activity
Specific function:
An acylphosphate + H(2)O = a carboxylate + phosphate
Gene Name:
yccX
Uniprot ID:
P0AB65
Molecular weight:
10300
Reactions
An acylphosphate + H(2)O = a carboxylate + phosphate.