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

• ChemBase ID: 160616
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@H]1O)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@H]2O)C)C1)C
• InChI: InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17+,18-,19-/m0/s1
• InChIKey: QADHLRWLCPCEKT-SLMGBJJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5,14-diol
• IUPAC Traditional name: 5-androstenediol
• Synonyms: (3β,17α)-Androst-5-ene-3,17-diol; Androst-5-ene-3β,17α-diol; 3β,17α-Dihydroxyandrost-5-ene; Δ5-Androstene-3β,17α-diol

Database IDs

• CAS Number: 1963-03-7
• PubChem SID: 162254751
• PubChem CID: 102192

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.7981772
• LogD (pH = 7.4): 2.7981772
• Log P: 2.7981772
• Molar Refractivity: 85.4812 cm^3
• Polarizability: 33.808178 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637455

A metabolite of 5-Androstenediol.

REFERENCES

• Ben-Nathan, D., et al.: J. Med. Microbiol., 48, 425 (1999)
• Schmidt, M., et al.: J. Endocrinol., 164, 161 (1999)
• Ripp, S., et al.: Drug Metab. Dispos., 30, 570 (1999)