(1S)-3-[(E)-2-[(1R,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

• ChemBase ID: 171982
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: C1[C@H](CCC(=C1/C=C/C1=C2[C@](CCC1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C)O
• Canonical SMILES: O[C@H]1CCC(=C(C1)/C=C/C1=C2CC[C@@H]([C@]2(CCC1)C)[C@@H](/C=C/[C@@H](C(C)C)C)C)C
• InChI: InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-26,29H,7-8,11,14-18H2,1-6H3/b10-9+,13-12+/t20-,22+,25-,26+,28+/m0/s1
• InChIKey: WHIQZYTVWTZJNO-GMPZOFGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3-[(E)-2-[(1R,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
• IUPAC Traditional name: isotachysterol2
• Synonyms: (3β,6E,22E)-9,10-Secoergosta-5(10),6,8(14),22-tetraen-3-ol; (6E)-9,10-Secoergosta-5(10),6,8(14),22-tetraen-3β-ol; Isotachysterol2; Isotachysterol

Database IDs

• CAS Number: 469-06-7
• PubChem SID: 164227892
• PubChem CID: 9547231

CALCULATED PROPERTIES

• Acid pKa: 18.314426
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.9489665
• LogD (pH = 7.4): 6.9489665
• Log P: 6.9489665
• Molar Refractivity: 129.6956 cm^3
• Polarizability: 49.86576 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I902450

A vitamin D analog.

REFERENCES

• Seamark, D.A., et al.: J. Steroid Biochem., 13, 1057 (1980)