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Record Information
Creation Date2006-08-12 22:34:16 UTC
Update Date2017-03-02 21:27:19 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-D-Glucose 1,6-bisphosphate
DescriptionGlucose 1,6-diphosphate (G-1,6-P2) is considered to be a major regulator of carbohydrate metabolism. It has been demonstrated that G-1,6-P2 is a potent activator (deinhibitor) of skeletal muscle phosphofructokinase (PFK) and phosphoglucomutase, while being an inhibitor of hexokinase (see Ref. 2). In addition, G-1,6-P2 has been shown to inhibit 6-phosphogluconate dehydrogenase in various rat tissues and fructose 1,6-bisphosphatase in bovine liver. Various factors and conditions affect the tissue content of G-1,6-P2. Specifically, anoxia induce a rapid fall in the content of G-l,6-P2 in brain. Glucose 1,6-diphosphate have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. The levels of G 1,6-P2 are reduced in the liver and in the muscle of rats with experimentally induced diabetes. In muscle of genetically dystrophic mice a decrease in the levels of G 1,6-P2 has been found, probably resulting from enhancement of glucose 1,6-P2 phosphatase activity. G 1,6-P2 is an inhibitor of hexokinase and its level is increased significantly after 5 min of exercise (~ 25%) and then decreased continuously. G 1,6-P2 is a potent allosteric activator of phosphofructokinase, and is markedly decreased in muscles of patients with glycogenosis type VII (muscle phosphofructokinase deficiency) and type V (muscle phosphorylase deficiency). Chronic alcohol intake produces an increase in the concentration of G 1,6-P2 in human muscle before the first sign of myopathy appears. When myopathy is present the level decreases to be similar of healthy humans. These changes could contribute to the decline in skeletal muscle performance. (PMID: 1449560 , 2018547 , 2003594 , 3407759 ).
alpha-D-Glucose 1,6-biphosphateChEBI
D-Glucose 1,6-biphosphateChEBI
a-D-Glucose 1,6-biphosphateGenerator
a-D-Glucose 1,6-biphosphoric acidGenerator
alpha-D-Glucose 1,6-biphosphoric acidGenerator
α-D-glucose 1,6-biphosphateGenerator
α-D-glucose 1,6-biphosphoric acidGenerator
a-D-Glucose 1,6-bisphosphateGenerator
a-D-Glucose 1,6-bisphosphoric acidGenerator
alpha-D-Glucose 1,6-bisphosphoric acidGenerator
α-D-glucose 1,6-bisphosphateGenerator
α-D-glucose 1,6-bisphosphoric acidGenerator
D-Glucose 1,6-biphosphoric acidGenerator
a-D-Glucose 1,6-bis(dihydrogen phosphate)HMDB
a-D-Glucose 1,6-diphosphateHMDB
alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranoseHMDB
alpha-D-Glucose 1,6-bis(dihydrogen phosphate)HMDB
alpha-D-Glucose 1,6-diphosphateHMDB
alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranoseHMDB
alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)HMDB
alpha-delta-Glucose 1,6-bisphosphateHMDB
alpha-delta-Glucose 1,6-diphosphateHMDB
D-Glucose 1,6-diphosphateHMDB
delta-Glucose 1,6-diphosphateHMDB
Glucose 1,6-bisphosphateHMDB
Glucose 1,6-diphosphateHMDB
beta-D-Glucose 1,6-(bis)phosphateMeSH
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxan-2-yl]methoxy}phosphonic acid
Traditional Nameglucose 1,6-bisphosphate
CAS Registry Number10139-18-1
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentHexose phosphates
Alternative Parents
  • 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
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.374Not Available
Predicted Properties
Water Solubility16.0 mg/mLALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.67 m3·mol-1ChemAxon
Polarizability24.96 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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 Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
Glycogen synthetase deficiencySMP00552Not Available
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisSMP00553Not Available
Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseSMP00554Not Available
Glycogenosis, Type VI. Hers diseaseSMP00555Not Available
Mucopolysaccharidosis VI. Sly syndromeSMP00556Not Available
Starch and Sucrose MetabolismSMP00058map00500
Sucrase-isomaltase deficiencySMP00557Not Available
Normal Concentrations
BloodDetected and Quantified98.0 +/- 17.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023185
KNApSAcK IDNot Available
Chemspider ID74362
KEGG Compound IDC01231
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03514
Metagene LinkHMDB03514
METLIN IDNot Available
PubChem Compound82400
PDB IDNot Available
ChEBI ID18148
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]


General function:
Involved in catalytic activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in cytochrome-c oxidase activity
Specific function:
This is the heme A-containing chain of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of the nucleoside breakdown products ribose-1-phosphate and deoxyribose-1-phosphate to the corresponding 5-phosphopentoses. May also catalyze the interconversion of glucose-1-phosphate and glucose-6-phosphate. Has low glucose 1,6-bisphosphate synthase activity.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Glucose 1,6-bisphosphate synthase using 1,3-bisphosphoglycerate as a phosphate donor and a series of 1-phosphate sugars as acceptors, including glucose 1-phosphate, mannose 1-phosphate, ribose 1-phosphate and deoxyribose 1-phosphate. 5 or 6-phosphosugars are bad substrates, with the exception of glucose 6-phosphate. Also synthesizes ribose 1,5-bisphosphate. Has only low phosphopentomutase and phosphoglucomutase activities.
Gene Name:
Uniprot ID:
Molecular weight:
Glyceric acid 1,3-biphosphate + Glucose 1-phosphate → 3-Phosphoglyceric acid + Alpha-D-Glucose 1,6-bisphosphatedetails