(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

• ChemBase ID: 3519
• Molecular Formular: C19H32O2
• Molecular Mass: 292.45618
• Monoisotopic Mass: 292.24023026
• SMILES: C1[C@@]2(C)[C@H](C[C@H](C1)O)CC[C@H]1[C@H]3[C@](CC[C@H]21)([C@H](CC3)O)C
• 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-/m0/s1
• InChIKey: CBMYJHIOYJEBSB-YSZCXEEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol; (1S,2S,5S,7S,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: 5α-androstane-3β,17β-diol
• Synonyms: 5-Alpha-Androstane-3-Beta,17beta-Diol; 5α-Androstane-3β,17β-diol; (3β,5α,17β)-Androstane-3,17-diol; 3β,17β-Androstanediol; 3β,17β-Dihydroxy-5α-androstane; 3β-Adiol; Maxterone; NSC 50891

Database IDs

• CAS Number: 571-20-0
• PubChem SID: 160966958; 46508740
• PubChem CID: 242332
• Chemspider ID: 211834
• Wikipedia Title: 5α-Androstane-3β,17β-diol

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.56
• LOG S: -4.18
• Solubility (Water): 1.93e-02 g/l

DETAILS

DrugBank - DB03882

Drug information: experimental

Toronto Research Chemicals - A637526

5α-Androstane-3β,17β-diol is a metabolite of Testosterone (T155000).

REFERENCES

• Monetti, G., et al.: J. Steroid Biochem., 25, 765 (1986)