alpha-D-Glucose 1,6-bisphosphate (ECMDB03514) (M2MDB000508)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
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
DescriptionAlpha-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
MOLSDFPDBSMILESInChI
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,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002f-9182000000-23bca820b90a45f17acbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00dl-0089000000-14b2732dbc26e1c46650View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-03di-0090000000-eff1032954c312ffe781View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-03di-0019000000-b6e1680b5b949ae7c8f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03xr-0069000000-63772b51257cee2af15aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-0092000000-65fab63b500e60a0ea01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-0190000000-bfbcf573cf5f756927f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-01b9-0790000000-757dcf8e67df0907f65aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-00di-0920000000-18f7c04ce401fda68354View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-014i-0090000000-e9698a8c472de2ec65b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00fr-0930000000-7f0cb15d50e589a9640fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0002-0910000000-4a92067b100f48729122View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0002-0390000000-c8d4b6af4a7e1dbc6766View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-004i-0069000000-b2d82f85ee47b9928a9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-004i-0091000000-e9e211cdeab0d7aab3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-0000900000-386775c642a8d4f6b7b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-0004900000-249416017fe86caa0eb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014i-0109200000-91fd1405fb3d3ce23e3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-014i-0309000000-71838f11ad810bfe78acView 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
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:
  • 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

Protein Details
1. Glucose-1-phosphate adenylyltransferase
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.
Protein Details
2. Phosphoglucosamine mutase
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.