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

• ChemBase ID: 153463
• Molecular Formular: C6H15O15P3
• Molecular Mass: 420.095583
• Monoisotopic Mass: 419.96237967
• SMILES: C1(C(C(C(C(C1OP(=O)(O)O)O)OP(=O)(O)O)OP(=O)(O)O)O)O
• Canonical SMILES: OC1C(OP(=O)(O)O)C(OP(=O)(O)O)C(C(C1O)OP(=O)(O)O)O
• InChI: InChI=1S/C6H15O15P3/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)
• InChIKey: MMWCIQZXVOZEGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
• IUPAC Traditional name: inositol 1,4,5-trisphosphate
• Synonyms: D-myo-Inositol 2,4,5-tris-phosphate ammonium sodium salt; D-myo-Inositol 1,3,4-tris-phosphate ammonium salt

Database IDs

• CAS Number: 92216-45-0; 93133-76-7
• MDL Number: MFCD00133232; MFCD00133235
• PubChem SID: 24895897; 24896036; 162247602
• PubChem CID: 806

CALCULATED PROPERTIES

• Acid pKa: 0.5363206
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -11.57853
• LogD (pH = 7.4): -15.176788
• 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

PROPERTIES

Safety Information

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

Product Information

• Linear Formula: C6H15O15P3 · 6NH3
• Empirical Formula (Hill Notation): C6H15O15P3 · x(NH3 + Na+)

DETAILS

Sigma Aldrich - I0146

Application
Used in the study of stereospecific binding of inositol trisphosphates, stimulates intracellular calcium release.

Sigma Aldrich - I3389

Biochem/physiol Actions
Occurs naturally in carbachol-stimulated rat parotid glands1 and in adrenal glomerular cells.2