2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,14-diol

• ChemBase ID: 1311
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: OC1C2(C(C3C(C4(C(=CC3)CC(O)CC4)C)CC2)CC1)C
• Canonical SMILES: OC1CCC2(C(=CCC3C2CCC2(C3CCC2O)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
• InChIKey: QADHLRWLCPCEKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,14-diol
• IUPAC Traditional name: androstenediol
• Synonyms: 5-Androstenediol

Database IDs

• PubChem SID: 46507476; 160964771
• PubChem CID: 223407

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.42
• LOG S: -3.72
• Solubility (Water): 5.50e-02 g/l

DETAILS

DrugBank - DB01524

• Drug Groups: illicit; experimental
• Description: An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-hydroxysteroid dehydrogenases). [PubChem]