tripotassium (1R,2R,3S,4R,5R,6S)-2,4-bis(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate

• ChemBase ID: 105075
• Molecular Formular: C6H12K3O15P3
• Molecular Mass: 534.366663
• Monoisotopic Mass: 533.83002461
• SMILES: [K+].[K+].[K+].O[C@@H]1[C@H](O)[C@@H](OP(=O)(O)[O-])[C@H](OP(=O)(O)[O-])[C@@H](O)[C@@H]1OP(=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-])O.[K+].[K+].[K+]
• InChI: InChI=1S/C6H15O15P3.3K/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12;;;/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18);;;/q;3*+1/p-3/t1-,2+,3+,4-,5-,6-;;;/m1.../s1
• InChIKey: MQMSEISCCNPXIL-ZKVWPJASSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: tripotassium (1R,2R,3S,4R,5R,6S)-2,4-bis(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate
• IUPAC Traditional name: tripotassium (1R,2R,3S,4R,5R,6S)-2,4-bis(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate
• Synonyms: D-myo-INOSITOL 1,4,5-TRISPHOSPHATE TRIPOTASSIUM SALT

Database IDs

• CAS Number: 103476-24-0
• PubChem SID: 162091941
• PubChem CID: 71299709

CALCULATED PROPERTIES

• Acid pKa: 0.5363206
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -11.57853
• LogD (pH = 7.4): -15.176788
• Log P: -4.1527076
• Molar Refractivity: 65.0286 cm^3
• Polarizability: 28.739426 Å^3
• Polar Surface Area: 269.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C, Store Under Nitrogen

DETAILS

MP Biomedicals - 02158354

Tripotassium Salt
Ins (1,4,5)P₃
Synthetic
Enantiomerically pure. Greater than 99% pure as per ^1 H and ^31 P NMR
Functions as a second messenger in the release of calcium from intracellular organelles; has been implicated as a mediator of phototransduction in Limulus photoreceptors where it effects changes in ion permeability and sodium ion currents.
Soluble in water.

REFERENCES

• Berridge, M.J. and Irvine, R.F., Nature , 312 : 315, (1984).
• Brown, J.E., et al., Nature , 311 : 160, (1984).
• Grado, C. and Ballou, C.E., J. Biol. Chem. , 236 : 54, (1961).
• Tomlinson, R.V. and Ballou, C.E., J. Biol. Chem. , 236 : 1902, (1961).
• Brockerhoff, H. and Ballou, C.E., J. Biol. Chem. , 236 : 1907, (1961).