{[(1S,2R,3R,4R,5R,6R)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid

• ChemBase ID: 171645
• Molecular Formular: C6H16O18P4
• Molecular Mass: 500.075484
• Monoisotopic Mass: 499.92871019
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@H]1OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)O)O)OP(=O)(O)O
• Canonical SMILES: O[C@@H]1[C@H](OP(=O)(O)O)[C@@H](OP(=O)(O)O)[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)OP(=O)(O)O
• InChI: InChI=1S/C6H16O18P4/c7-1-2(8)4(22-26(12,13)14)6(24-28(18,19)20)5(23-27(15,16)17)3(1)21-25(9,10)11/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2-,3-,4+,5-,6-/m1/s1
• InChIKey: MRVYFOANPDTYBY-XCMZKKERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1S,2R,3R,4R,5R,6R)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid
• IUPAC Traditional name: [(1S,2R,3R,4R,5R,6R)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid
• Synonyms: myo-Inositol 1,4,5,6-Tetrakis(Dihydrogen Phosphate); Inositol 1,4,5,6-Tetraphosphate; Ins(1,3,4,5)P4; myo-Inositol 1,4,5,6-Tetrakis(phosphate)

Database IDs

• CAS Number: 121010-58-0
• PubChem SID: 164227555
• PubChem CID: 14033625

CALCULATED PROPERTIES

• Acid pKa: 0.23738626
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -14.319474
• LogD (pH = 7.4): -19.440441
• Log P: -4.2762737
• Molar Refractivity: 79.2666 cm^3
• Polarizability: 33.802597 Å^3
• Polar Surface Area: 307.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I666005

Ins(1,4,5,6)P4, a biol. active cell constituent, was recently advocated as a substrate of human Ins(3,4,5,6)P4 1-kinase (hITPK1), because stereochemistry factors were believed relatively unimportant to specificity. Ins(1,4,5,6)P4 is phosphorylated by inos

REFERENCES

• Majerus, P; J Biol Chem 1999, 274, 10669, Adelt, S; Bioorg Med Chem Lett 2001, 11, 2705, Shears, S; Biochem J 2004, 377, 265