disodium [(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl phosphate

• ChemBase ID: 169675
• Molecular Formular: C6H11Na2O9P
• Molecular Mass: 304.099441
• Monoisotopic Mass: 303.99360712
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1COP(=O)([O-])[O-])O)O)O)O.[Na+].[Na+]
• Canonical SMILES: OC1O[C@@H](COP(=O)([O-])[O-])[C@H]([C@@H]([C@@H]1O)O)O.[Na+].[Na+]
• InChI: InChI=1S/C6H13O9P.2Na/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8;;/h2-10H,1H2,(H2,11,12,13);;/q;2*+1/p-2/t2-,3-,4+,5-,6?;;/m1../s1
• InChIKey: CHIBNKGHYAQTQY-DUMCKRSRSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl phosphate
• IUPAC Traditional name: disodium D-glucopyranose 6-phosphate
• Synonyms: D-Glucose 6-(Dihydrogen Phosphate) Disodium Salt Hydrate; D-Glucose 6-(Disodium Phosphate) Hydrate; Disodium D-Glucose 6-Phosphate Hydrate; D-Glucose 6-Phosphate Disodium Salt Hydrate

Database IDs

• PubChem SID: 162263807
• PubChem CID: 15639937

CALCULATED PROPERTIES

• Acid pKa: 1.2229363
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -5.498048
• LogD (pH = 7.4): -6.5882425
• Log P: -3.0561051
• Molar Refractivity: 44.5529 cm^3
• Polarizability: 19.553816 Å^3
• Polar Surface Area: 162.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 135-140°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G596805

A phosphorylated glucose derivative that is a key intermediate in biological processes such as glycolysis, glycogenolysis, pentose phosphate pathway. At elevated levels inhibit brain hexokinase and glycolysis.

REFERENCES

• Okubo, M. et al.: Metab., 37, 1171 (1988)
• Henriksen, J.E. et al.: Metab. Clin. Exp., 46, 598 (1988)
• Oyama, J. et al.: Enndocrinol., 80, 707 (1988)
• Newsholme, E.A. et al.: Biochem. J., 104, 47P (1988)