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

• ChemBase ID: 132310
• Molecular Formular: C6H12NaO9P
• Molecular Mass: 282.117611
• Monoisotopic Mass: 282.01166288
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)O)O)O)OP(=O)(O)[O-].[Na+]
• Canonical SMILES: O[C@@H]1O[C@H](COP(=O)(O)[O-])[C@H]([C@@H]([C@H]1O)O)O.[Na+]
• InChI: InChI=1S/C6H13O9P.Na/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;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1
• InChIKey: ZALKNDISPIVVKC-WYRLRVFGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl hydrogen phosphate
• IUPAC Traditional name: sodium [(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl hydrogen phosphate
• Synonyms: G-6-P Na; Robison ester; D-Glucose 6-phosphate sodium salt; D(+)-Glucopyranose 6-phosphate sodium salt

Database IDs

• CAS Number: 54010-71-8
• EC Number: 258-921-0
• MDL Number: MFCD00006611
• Beilstein Number: 5787568
• PubChem SID: 24895324; 162226587
• PubChem CID: 23702133

CALCULATED PROPERTIES

• Acid pKa: 1.2229363
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.498048
• LogD (pH = 7.4): -6.5882425
• Log P: -3.0561051
• Molar Refractivity: 45.6746 cm^3
• Polarizability: 19.673773 Å^3
• Polar Surface Area: 159.74 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless to very faintly yellow
• Apperance: crystalline
• Melting Point: 204 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +34±1°, c = 10% in H2O; [α]25/D +33°, c = 10 in H2O
• pH: 3.5-4.5 (25 °C, 0.5 g/10 mL in H2O)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (enzymatic)
• Grade: Sigma Grade
• Quality Level: PREMIUM
• Quality: anhydrous; crystallized
• Empirical Formula (Hill Notation): C6H12NaO9P

DETAILS

Sigma Aldrich - G7879

Biochem/physiol Actions
In cells, D-glucose 6-phosphate (G6P) is generated when glucose is phosphorylated by hexokinase or glucokinase or by the conversion of glucose-1-phosphate by phosphoglucomutase during glycogenolysis. G6P lies at the beginning of both glycolysis and the pentose phosphate pathways. It also can be stored as glycogen when blood glucose levels are high.
Caution
Non-hygroscopic, and very stable to atmospheric moisture at room temperature, unlike the disodium salt.
包装
1, 5, 25 g in poly bottle
500 mg in poly bottle

Sigma Aldrich - 285978

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 49282

Application
Substrate for the determination of glucose-6-phosphate dehydrogenase, EC 1.1.1.491