(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-diol

• ChemBase ID: 160620
• Molecular Formular: C19H32O2
• Molecular Mass: 292.45618
• Monoisotopic Mass: 292.24023026
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1
• InChIKey: CBMYJHIOYJEBSB-GCXXXECGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: β-androstane-3a,17b-diol
• Synonyms: (3α,5β,17β)-Androstane-3,17-diol; 5β-Androstane-3α,17β-diol; 3α,17β-Dihydroxyetiocholane; Etiocholanediol; β-Androstane-3α,17β-diol; 5β-Androstan-3α,17β-diol

Database IDs

• CAS Number: 1851-23-6
• PubChem SID: 162254755
• PubChem CID: 134494

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.2037566
• LogD (pH = 7.4): 3.2037568
• Log P: 3.2037568
• Molar Refractivity: 84.6312 cm^3
• Polarizability: 34.047752 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637485

A metabolite of Testosterone (T155000).

REFERENCES

• Kulkarni, S., et al.: Xenobiotica, 35, 955 (2005)
• Kicman, A., et al.: Br. J. Pharmacol., 154, 502 (2005)
• Fragkaki, A., et al.: Steroids, 74, 172 (2005)