trisodium hydrate (3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonatooxy)hexyl hydrogen phosphate

• ChemBase ID: 153196
• Molecular Formular: C6H13Na3O13P2
• Molecular Mass: 424.076452
• Monoisotopic Mass: 423.95244658
• SMILES: C([C@H]([C@H]([C@@H](C(=O)COP(=O)(O)[O-])O)O)O)OP(=O)([O-])[O-].O.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]([C@H]([C@@H](C(=O)COP(=O)(O)[O-])O)O)COP(=O)([O-])[O-].O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C6H14O12P2.3Na.H2O/c7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16;;;;/h3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16);;;;1H2/q;3*+1;/p-3/t3-,5-,6-;;;;/m1..../s1
• InChIKey: ISLNIFDAODOXHN-GNWSQLALSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium hydrate (3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonatooxy)hexyl hydrogen phosphate
• IUPAC Traditional name: trisodium hydrate (3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonatooxy)hexyl hydrogen phosphate
• Synonyms: D(+)Fructofuranose 1,6-diphosphate trisodium salt hydrate; Harden-Young ester; Hexose diphosphate trisodium salt hydrate; D-Fructose 1,6-bisphosphate trisodium salt hydrate

Database IDs

• CAS Number: 38099-82-0(anhydrous)
• MDL Number: MFCD03427650
• PubChem SID: 24894921; 162247335
• PubChem CID: 71311607

CALCULATED PROPERTIES

• Acid pKa: 1.0062538
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -8.369056
• LogD (pH = 7.4): -10.380598
• Log P: -3.514164
• Molar Refractivity: 55.9425 cm^3
• Polarizability: 24.197052 Å^3
• Polar Surface Area: 219.77 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C6H11Na3O12P2 · xH2O

DETAILS

Sigma Aldrich - F6803

Packaging
10 mg in autosample vial
Biochem/physiol Actions
Fructose-1,6-biphosphate (F1,6P) is a glycolytic intermediate produced by the transfer of a phosphate from ATP to fructose-6-phosphate by the enzyme phosphofructokinase. Fructose-1,6-biphosphate, along with fructose-2,6-biphosphate, modulates the activity of phosphofructokinase-1 (PFK-1), the rate-limiting step in glycolysis. During glycolysis, aldolase splits Fructose-1,6-biphosphate into dihydroxacetone phosphate (DHAP) and glyceraldehyde phosphate. Fructose-1,6-biphosphate is also an allosteric activator of the M2 isoform of Pyruvate Kinase (PK-M2), the predominant form of pyruvate kinase in cancer cells.