(2S)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-1H-inden-1-yl]propyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 171638
• Molecular Formular: C20H30O4S
• Molecular Mass: 366.5148
• Monoisotopic Mass: 366.18648044
• SMILES: C1CC[C@]2([C@H]([C@H]1O)CC[C@@H]2[C@@H](COS(=O)(=O)c1ccc(cc1)C)C)C
• Canonical SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CCC[C@@H]2O)COS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C20H30O4S/c1-14-6-8-16(9-7-14)25(22,23)24-13-15(2)17-10-11-18-19(21)5-4-12-20(17,18)3/h6-9,15,17-19,21H,4-5,10-13H2,1-3H3/t15-,17-,18+,19+,20-/m1/s1
• InChIKey: CZKSQENRQZPNOS-LFZDHENXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-1H-inden-1-yl]propyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: (2S)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydroinden-1-yl]propyl 4-methylbenzenesulfonate
• Synonyms: (βS,1R,3aR,4S,7aR)-Octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-ethanol 1-(4-Methylbenzenesulfonate); Inhoffen Lythgoe Diol Monotosylate

Database IDs

• CAS Number: 66774-80-9
• PubChem SID: 164227548
• PubChem CID: 13519431

CALCULATED PROPERTIES

• Acid pKa: 19.423426
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.4375687
• LogD (pH = 7.4): 4.437569
• Log P: 4.437569
• Molar Refractivity: 99.0622 cm^3
• Polarizability: 40.0201 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I657005

Vitamin D analog.

REFERENCES

• Bouillon, R., et al.: J. Biol. Chem., 267, 3044 (1992)
• Bouillon, R., et al.: Endocrine Rev., 16, 200 (1992)