tetrakis(cyclohexanamine); {[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]oxy}phosphonic acid

• ChemBase ID: 133808
• Molecular Formular: C30H66N4O12P2
• Molecular Mass: 736.812162
• Monoisotopic Mass: 736.41524683
• SMILES: C1CCC(CC1)N.C1CCC(CC1)N.C1CCC(CC1)N.C1CCC(CC1)N.C([C@H]([C@H]([C@@H](C(=O)COP(=O)(O)O)O)O)O)OP(=O)(O)O
• Canonical SMILES: O[C@@H]([C@H]([C@@H](C(=O)COP(=O)(O)O)O)O)COP(=O)(O)O.NC1CCCCC1.NC1CCCCC1.NC1CCCCC1.NC1CCCCC1
• InChI: InChI=1S/4C6H13N.C6H14O12P2/c4*7-6-4-2-1-3-5-6;7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16/h4*6H,1-5,7H2;3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16)/t;;;;3-,5-,6-/m....1/s1
• InChIKey: NVWGDAYGDKPKLQ-CBCSRFDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrakis(cyclohexanamine); {[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]oxy}phosphonic acid
• IUPAC Traditional name: tetrakis(cyclohexylamine) D-fructose 1,6-bisphosphate
• Synonyms: D(+)Fructofuranose 1,6-diphosphate; Harden-Young ester; Hexose diphosphate; D-Fructose 1,6-bisphosphate tetra(cyclohexylammonium) salt

Database IDs

• CAS Number: 103213-44-1
• PubChem SID: 162228085
• PubChem CID: 44144639

CALCULATED PROPERTIES

• Acid pKa: 1.0062538
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -8.369056
• LogD (pH = 7.4): -10.380598
• Log P: -3.514164
• Molar Refractivity: 59.3076 cm^3
• Polarizability: 24.558372 Å^3
• Polar Surface Area: 211.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

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: ≥95%
• Impurities: Hexose monophosphates, essentially free

DETAILS

Sigma Aldrich - F0752

Application
D-Fructose-1,6-bisphosphate (FBP), a common metabolic sugar, is the precursor of glyceraldehyde 3-phosphate and dihydroxyacetone phosphate in the glycolytic pathway. It is an allosteric activator of enzymes such as pyruvate kinase and a substrate used to identify and characterize enzymes such as fructose-1,6-bisphosphate aldolase(s) and fructose-1, 6-bisphosphatase(s). FBP is studied as a neuroprotective agent in brain injury.