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

• ChemBase ID: 171646
• Molecular Formular: C6H15O15P3
• Molecular Mass: 420.095583
• Monoisotopic Mass: 419.96237967
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@H]1O)O)O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O
• Canonical SMILES: O[C@@H]1[C@@H](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/C6H15O15P3/c7-1-2(8)4(19-22(10,11)12)6(21-24(16,17)18)5(3(1)9)20-23(13,14)15/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2-,3+,4-,5-,6-/m0/s1
• InChIKey: GKDKOMAJZATYAY-PTQMNWPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1R,2S,3S,4R,5R,6S)-3,4,5-trihydroxy-2,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
• IUPAC Traditional name: [(1R,2S,3S,4R,5R,6S)-3,4,5-trihydroxy-2,6-bis(phosphonooxy)cyclohexyl]oxyphosphonic acid
• Synonyms: Ins(1,2,3)P3; myo-Inositol 1,2,3-Trisphosphate

Database IDs

• CAS Number: 1311140-98-3
• PubChem SID: 164227556
• PubChem CID: 9910016

CALCULATED PROPERTIES

• Acid pKa: 0.3988759
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -11.661557
• LogD (pH = 7.4): -15.456751
• Log P: -4.1527076
• Molar Refractivity: 68.3937 cm^3
• Polarizability: 29.101633 Å^3
• Polar Surface Area: 260.97 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I666010

Ins(1,2,3)P3 is an important chelator of iron cations not strongly bound to proteins, which avoids iron redox cycling and the associated production of free radicals.

REFERENCES

• Graf, E., et al.: J. Biol. Chem., 262, 11647 (1987)
• Petrat, F., et al.: Biol. Chem., 383, 489 (1987)
• Merkofer, M., et al.: Chem. Res. Toxicol., 19, 1263 (1987)