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

• ChemBase ID: 178536
• Molecular Formular: C20H32OS
• Molecular Mass: 320.53248
• Monoisotopic Mass: 320.21738664
• SMILES: [C@H]12[C@H](C[C@H]3[C@](C1)([C@@H]1[C@@H](CC3)[C@H]3[C@](CC1)([C@](CC3)(O)C)C)C)S2
• Canonical SMILES: C[C@]12C[C@H]3S[C@H]3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C
• InChI: InChI=1S/C20H32OS/c1-18-11-17-16(22-17)10-12(18)4-5-13-14(18)6-8-19(2)15(13)7-9-20(19,3)21/h12-17,21H,4-11H2,1-3H3/t12-,13+,14-,15-,16-,17+,18-,19-,20-/m0/s1
• InChIKey: UPLPHRJJTCUQAY-WIRWPRASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,15,16-trimethyl-5-thiapentacyclo[9.7.0.0^2,^8.0^4,^6.0^1^2,^1^6]octadecan-15-ol
• IUPAC Traditional name: (1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,15,16-trimethyl-5-thiapentacyclo[9.7.0.0^2,^8.0^4,^6.0^1^2,^1^6]octadecan-15-ol
• Synonyms: (2α,3α,5α,17β)-2,3-Epithio-17-methylandrostan-17-ol; 2α,3α-Epithio-17α-methyl-5α-androstan-17β-ol; Hemapolin; 2,3-Thioepoxy Madol

Database IDs

• CAS Number: 4267-80-5
• PubChem SID: 164234446
• PubChem CID: 71752521

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.099144
• LogD (pH = 7.4): 4.099144
• Log P: 4.099144
• Molar Refractivity: 93.3508 cm^3
• Polarizability: 37.613667 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T344425

An epithio derivative of Madol (M108000), an anabolic steroid.

REFERENCES

• So, S., et al.: J. Med. Chem., 40, 4347 (1997)
• Camenisch, G., et al.: J. Pharm. Sci., 6, 313 (1997)
• Yazdanian, M., et al.: Pharm. Res., 15, 1490 (1997)