(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptan-2-ol

• ChemBase ID: 163335
• Molecular Formular: C33H58O2Si
• Molecular Mass: 514.89792
• Monoisotopic Mass: 514.42060763
• SMILES: C1C/C(=C\C=C/2\C[C@H](CCC2=C)O[Si](C(C)(C)C)(C)C)/[C@H]2[C@](C1)([C@H](CC2)[C@@H](CCCC(O)(C)C)C)C
• Canonical SMILES: C=C1CC[C@@H](C/C/1=C/C=C/1\CCC[C@]2([C@H]1CC[C@@H]2[C@@H](CCCC(O)(C)C)C)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C33H58O2Si/c1-24-15-18-28(35-36(9,10)31(3,4)5)23-27(24)17-16-26-14-12-22-33(8)29(19-20-30(26)33)25(2)13-11-21-32(6,7)34/h16-17,25,28-30,34H,1,11-15,18-23H2,2-10H3/b26-16+,27-17-/t25-,28+,29-,30+,33-/m1/s1
• InChIKey: CTZMHDJIUFEYKE-NXMZLKDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptan-2-ol
• IUPAC Traditional name: (6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-methylheptan-2-ol
• Synonyms: (3β,5Z,7E)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-9,10-secocholesta-5,7,10(19)-triene-25-diol; 3-O-tert-Butyldimethylsilyl-25-Hydroxycholecalciferol; 3-O-tert-Butyldimethylsilyl-25-hydroxyvitamin D3; 3-O-TBDMS 25-OH Vitamin D3; 3-O-tert-Butyldimethylsilyl Calcifediol

Database IDs

• CAS Number: 140710-90-3
• PubChem SID: 162257470
• PubChem CID: 71314397

CALCULATED PROPERTIES

• Acid pKa: 18.53077
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 7.7587
• LogD (pH = 7.4): 7.7587
• Log P: 7.7587
• Molar Refractivity: 154.9087 cm^3
• Polarizability: 62.897964 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B691230

A protected Calcifediol (C125700), a hydroxylated metabolite of Vitamin D3.

REFERENCES

• Ray, R. et al.: Steroids, 57, 142 (1992)