Record Information
Version2.0
Creation Date2012-05-31 13:59:29 -0600
Update Date2015-06-03 15:54:24 -0600
Secondary Accession Numbers
  • ECMDB03514
Identification
Name:alpha-D-Glucose 1,6-bisphosphate
Description:Alpha-D-glucose 1,6-bisphosphate is considered to be a major regulator of carbohydrate metabolism. Glucose 1,6-diphosphate (G 1,6-P2) have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. G 1,6-P2 is a potent allosteric activator of phosphofructokinase.
Structure
Thumb
Synonyms:
  • α-D-glucopyranose, 1,6-bis(dihydrogen phosphate)
  • α-D-glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
  • α-D-glucose-1,6-P2
  • α-D-glucose-1,6-P2
  • a-D-1,6-Bis(dihydrogen phosphate) glucopyranose
  • a-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • a-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
  • a-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
  • A-D-Glucose 1,6-bis(dihydrogen phosphate)
  • a-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • A-D-Glucose 1,6-bisphosphate
  • a-D-Glucose 1,6-bisphosphoric acid
  • A-D-Glucose 1,6-diphosphate
  • a-D-Glucose 1,6-diphosphoric acid
  • a-D-Glucose-1,6-P2
  • a-delta-1,6-Bis(dihydrogen phosphate) glucopyranose
  • a-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • a-delta-Glucose 1,6-bis(dihydrogen phosphate)
  • a-delta-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • a-delta-Glucose 1,6-bisphosphate
  • a-delta-Glucose 1,6-bisphosphoric acid
  • a-delta-Glucose 1,6-diphosphate
  • a-delta-Glucose 1,6-diphosphoric acid
  • a-δ-1,6-Bis(dihydrogen phosphate) glucopyranose
  • a-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • a-δ-Glucose 1,6-bis(dihydrogen phosphate)
  • a-δ-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • a-δ-Glucose 1,6-bisphosphate
  • a-δ-Glucose 1,6-bisphosphoric acid
  • a-δ-Glucose 1,6-diphosphate
  • a-δ-Glucose 1,6-diphosphoric acid
  • Alpha-D-1,6-Bis(dihydrogen phosphate) Glucopyranose
  • alpha-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • Alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
  • alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
  • Alpha-D-Glucose 1,6-bis(dihydrogen phosphate)
  • alpha-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • Alpha-D-Glucose 1,6-bisphosphate
  • alpha-D-Glucose 1,6-bisphosphoric acid
  • Alpha-D-Glucose 1,6-diphosphate
  • alpha-D-Glucose 1,6-diphosphoric acid
  • Alpha-D-Glucose-1,6-P2
  • Alpha-delta-1,6-Bis(dihydrogen phosphate) Glucopyranose
  • alpha-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • Alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)
  • alpha-delta-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • Alpha-delta-Glucose 1,6-bisphosphate
  • alpha-delta-Glucose 1,6-bisphosphoric acid
  • Alpha-delta-Glucose 1,6-diphosphate
  • alpha-delta-Glucose 1,6-diphosphoric acid
  • D-Glucose 1,6-biphosphate
  • D-Glucose 1,6-biphosphoric acid
  • D-Glucose 1,6-bisphosphate
  • D-Glucose 1,6-bisphosphoric acid
  • D-Glucose 1,6-diphosphate
  • D-Glucose 1,6-diphosphoric acid
  • Delta-Glucose 1,6-diphosphate
  • delta-Glucose 1,6-diphosphoric acid
  • Glucose 1,6-bisphosphate
  • Glucose 1,6-bisphosphoric acid
  • Glucose 1,6-diphosphate
  • Glucose 1,6-diphosphoric acid
  • Glucose-1,6-bisphosphate
  • Glucose-1,6-bisphosphoric acid
  • Glucose-1,6-diphosphate
  • Glucose-1,6-diphosphoric acid
  • α-D-1,6-Bis(dihydrogen phosphate) glucopyranose
  • α-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • α-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
  • α-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
  • α-D-Glucose 1,6-bis(dihydrogen phosphate)
  • α-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • α-D-Glucose 1,6-bisphosphate
  • α-D-Glucose 1,6-bisphosphoric acid
  • α-D-Glucose 1,6-diphosphate
  • α-D-Glucose 1,6-diphosphoric acid
  • α-D-Glucose-1,6-P2
  • α-δ-1,6-Bis(dihydrogen phosphate) glucopyranose
  • α-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
  • α-δ-Glucose 1,6-bis(dihydrogen phosphate)
  • α-δ-Glucose 1,6-bis(dihydrogen phosphoric acid)
  • α-δ-Glucose 1,6-bisphosphate
  • α-δ-Glucose 1,6-bisphosphoric acid
  • α-δ-Glucose 1,6-diphosphate
  • α-δ-Glucose 1,6-diphosphoric acid
  • δ-Glucose 1,6-diphosphate
  • δ-Glucose 1,6-diphosphoric acid
Chemical Formula:C6H14O12P2
Weight:Average: 340.1157
Monoisotopic: 339.996048936
InChI Key:RWHOZGRAXYWRNX-VFUOTHLCSA-N
InChI:InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1
CAS number:10139-18-1
IUPAC Name:{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:glucose 1,6-bisphosphate
SMILES:O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-4.374PhysProp
Predicted Properties
PropertyValueSource
Water Solubility16 g/LALOGPS
logP-1.6ALOGPS
logP-3.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.67 m³·mol⁻¹ChemAxon
Polarizability24.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9422000000-7bfff1b0b2d51cca5dffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fr5-7922130000-d6ba2057c5f43a10b976View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002f-9182000000-23bca820b90a45f17acbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2169000000-7496db21481f5c6646f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-8194000000-0ab11c338e7462b1784eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9710000000-04febc887536086e1a99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7319000000-8f0f5f6bb5550e944766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e67858a197b35311ba75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-44fd1ff1d686ff20aa4fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Cadefau JA, Andres V, Carreras J, Vernet M, Grau JM, Urbano-Marquez A, Cusso R: Glucose 1,6-bisphosphate and fructose 2,6-bisphosphate in muscle from healthy humans and chronic alcoholic patients. Alcohol Alcohol. 1992 May;27(3):253-6. Pubmed: 1449560
  • 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
  • Katz A, Sahlin K, Broberg S: Regulation of glucose utilization in human skeletal muscle during moderate dynamic exercise. Am J Physiol. 1991 Mar;260(3 Pt 1):E411-5. Pubmed: 2003594
  • Katz A: G-1,6-P2, glycolysis, and energy metabolism during circulatory occlusion in human skeletal muscle. Am J Physiol. 1988 Aug;255(2 Pt 1):C140-4. Pubmed: 3407759
  • 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
  • Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. Pubmed: 2018547
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18148
HMDB IDHMDB03514
Pubchem Compound ID82400
Kegg IDC01231
ChemSpider ID74362
Wikipedia IDNot Available
BioCyc IDALPHA-GLUCOSE-16-BISPHOSPHATE
EcoCyc IDALPHA-GLUCOSE-16-BISPHOSPHATE
Ligand ExpoG16

Enzymes

General function:
Involved in glycogen biosynthetic process
Specific function:
ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose
Gene Name:
glgC
Uniprot ID:
P0A6V1
Molecular weight:
48697
Reactions
ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of glucosamine-6-phosphate to glucosamine-1-phosphate. Can also catalyze the formation of glucose-6-P from glucose-1-P, although at a 1400-fold lower rate
Gene Name:
glmM
Uniprot ID:
P31120
Molecular weight:
47543
Reactions
Alpha-D-glucosamine 1-phosphate = D-glucosamine 6-phosphate.