(1S,2E,4R)-4-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-1-cyclopropylpent-2-en-1-ol

• ChemBase ID: 162437
• Molecular Formular: C39H68O3Si2
• Molecular Mass: 641.12642
• Monoisotopic Mass: 640.4706991
• SMILES: [C@@H]1(C[C@@H](C/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C2CC2)O)C)C)/C1=C)O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: O[C@@H](C1CC1)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C\1/C[C@H](C[C@@H](C1=C)O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)C
• InChI: InChI=1S/C39H68O3Si2/c1-27(16-23-35(40)30-18-19-30)33-21-22-34-29(15-14-24-39(33,34)9)17-20-31-25-32(41-43(10,11)37(3,4)5)26-36(28(31)2)42-44(12,13)38(6,7)8/h16-17,20,23,27,30,32-36,40H,2,14-15,18-19,21-22,24-26H2,1,3-13H3/b23-16+,29-17+,31-20+/t27-,32-,33-,34+,35-,36+,39-/m1/s1
• InChIKey: DIMYHZDULFSWLS-YFSXTQNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2E,4R)-4-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-1-cyclopropylpent-2-en-1-ol
• IUPAC Traditional name: (1S,2E,4R)-4-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-1-cyclopropylpent-2-en-1-ol
• Synonyms: (αS)-α-[(1E,3R)-3-[(1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1H-inden-1-yl]-1-buten-1-yl]cyclopropanemethanol; (5E)-1,3-Di-O-(tert-Butyldimethylsilyl)-calcipotriene; Bis-O-(tert-butyldimethylsilyl)-trans-calcipotriol

Database IDs

• CAS Number: 112849-27-1
• PubChem SID: 162256572
• PubChem CID: 13917667

CALCULATED PROPERTIES

• Acid pKa: 17.762907
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 9.1311
• LogD (pH = 7.4): 9.1311
• Log P: 9.1311
• Molar Refractivity: 185.1455 cm^3
• Polarizability: 76.58346 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B588580

Protected trans-Calcipotriol, a vitamin D analog.

REFERENCES

• Ashcroft, D., et al.: Brit. Med. J., 320, 963 (2000)
• Steinmeyer, A., et al.: Steroids, 66, 257 (2000)