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

• ChemBase ID: 154512
• Molecular Formular: C6H17O21P5
• Molecular Mass: 580.055385
• Monoisotopic Mass: 579.89504071
• 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)OP(=O)(O)O)OP(=O)(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]1OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O
• InChI: InChI=1S/C6H17O21P5/c7-1-2(23-28(8,9)10)4(25-30(14,15)16)6(27-32(20,21)22)5(26-31(17,18)19)3(1)24-29(11,12)13/h1-7H,(H2,8,9,10)(H2,11,12,13)(H2,14,15,16)(H2,17,18,19)(H2,20,21,22)/t1-,2-,3+,4-,5-,6-/m1/s1
• InChIKey: CTPQAXVNYGZUAJ-UOTPTPDRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1R,2S,3S,4R,5S,6R)-2-hydroxy-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
• IUPAC Traditional name: [(1R,2S,3S,4R,5S,6R)-2-hydroxy-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxyphosphonic acid
• Synonyms: L-myo-Inositol 1,2,3,4,5-pentakis-phosphate; D-myo-Inositol 1,2,3,5,6-pentakis-phosphate

Database IDs

• CAS Number: 26326-85-2
• MDL Number: MFCD08061883
• PubChem SID: 162248651
• PubChem CID: 11706915

CALCULATED PROPERTIES

• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -14.501955
• LogD (pH = 7.4): -19.744932
• Log P: -4.39984
• Molar Refractivity: 90.1395 cm^3
• Polarizability: 38.50862 Å^3
• Polar Surface Area: 354.03 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false
• Acid pKa: 0.18812706

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC)
• Empirical Formula (Hill Notation): C6H17O21P5

DETAILS

Sigma Aldrich - 03181

Biochem/physiol Actions
The metabolite inositol is a precursor of inositides, which have an important impact on diverse areas of cellular regulation2.
General description
Aluminum was shown to increase the activity of multiple inositol polyphosphate phosphatathase(MIPP) in hepatic mammalian cells. This cased a decrease in the MIPP substrate, Ins(1,2,3,5,6)P5. 1