(1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,16-dimethyl-5-thiapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-ol

• ChemBase ID: 168104
• Molecular Formular: C19H30OS
• Molecular Mass: 306.5059
• Monoisotopic Mass: 306.20173658
• SMILES: [C@H]12[C@H](C[C@H]3[C@](C1)([C@@H]1[C@@H](CC3)[C@H]3[C@](CC1)([C@H](CC3)O)C)C)S2
• Canonical SMILES: O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C[C@H]1S[C@H]1C2
• InChI: InChI=1S/C19H30OS/c1-18-8-7-14-12(13(18)5-6-17(18)20)4-3-11-9-15-16(21-15)10-19(11,14)2/h11-17,20H,3-10H2,1-2H3/t11-,12-,13-,14-,15-,16+,17-,18-,19-/m0/s1
• InChIKey: OBMLHUPNRURLOK-XGRAFVIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,16-dimethyl-5-thiapentacyclo[9.7.0.0^2,^8.0^4,^6.0^1^2,^1^6]octadecan-15-ol
• IUPAC Traditional name: thiodrol
• Synonyms: (2α,3α,5α,17β)-2,3-Epithioandrostan-17-ol; 2α,3α-Epithio-5α-androstan-17β-ol; 10275S; Epithiostanol; NSC 194684; Thiodrol; Epitiostanol

Database IDs

• CAS Number: 2363-58-8
• PubChem SID: 162262236
• PubChem CID: 443935

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.8185675
• LogD (pH = 7.4): 3.8185675
• Log P: 3.8185675
• Molar Refractivity: 88.7126 cm^3
• Polarizability: 35.769405 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E588800

An anabolic steroid that exhibits androgenic, myogenic, anabolic, anticatabolic, progestational, deciduomatogenic, and antiestrogenic activities. An anti-estrogen with anti-mammry cancer agent.

REFERENCES

• Miyake, T. et al.: Proc. Int. Congr. Horm. Steroids, 2, 616 (1967)
• Miyake, T.: Endocrinol. Jap., 17, 313 (1967)
• Hori, T. et al.: Prog. Cancer Res. Ther., 10, 159 (1967)