(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-7,7,7-trifluoro-6-hydroxy-6-(trifluoromethyl)heptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

• ChemBase ID: 168860
• Molecular Formular: C27H38F6O3
• Molecular Mass: 524.5792392
• Monoisotopic Mass: 524.2725144
• SMILES: C1[C@H](C[C@@H](C(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)C)O)O
• Canonical SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CCCC(C(F)(F)F)(C(F)(F)F)O)C)C)/C1
• InChI: InChI=1S/C27H38F6O3/c1-16(6-4-13-25(36,26(28,29)30)27(31,32)33)21-10-11-22-18(7-5-12-24(21,22)3)8-9-19-14-20(34)15-23(35)17(19)2/h8-9,16,20-23,34-36H,2,4-7,10-15H2,1,3H3/b18-8+,19-9-/t16-,20-,21-,22+,23+,24-/m1/s1
• InChIKey: XPYGGHVSFMUHLH-UUSULHAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-7,7,7-trifluoro-6-hydroxy-6-(trifluoromethyl)heptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: hornel
• Synonyms: (1R,4S,5Z)-4-Methylene-5-[(2E)-2-[1-[(1R)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)hexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol; 26,26,26,27,27,27-Hexafluoro-1,25-dihydroxyvitamin D3; Flocacitriol; Flocalcitriol; (1α,3β,5Z,7E)-26,26,26,27,27,27-Hexafluoro-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol; F6-1α,25-Dihydroxyvitamin D3; Fulstan; Hornel; Ro 23-4194; ST 630; (+)-(5Z,7E)-26,26,26,27,27,27-Hexafluoro-9,10-secocholesta-5,7,10(19)-triene-1α,3β,25-triol; Falecalcitriol

Database IDs

• CAS Number: 83805-11-2
• PubChem SID: 162262992
• PubChem CID: 5282190

CALCULATED PROPERTIES

• Acid pKa: 7.9947715
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.5459313
• LogD (pH = 7.4): 5.4490504
• Log P: 5.5473175
• Molar Refractivity: 127.9355 cm^3
• Polarizability: 47.94884 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F101110

Hexafluorinated analog of Calcitriol (C144500). A more potent therapeutic agent for secondary hyperparathyroidism.

REFERENCES

• Imanishi, Y. et al.: J. Steroid Biochem. Mol. Biol., 70, 243 (1999)
• Morii, H. et al.: Clin. Calc., 15, 29 (1999)
• Brown, A.J. et al.: Treat. Endocrinol., 1, 313 (1999)