(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one

• ChemBase ID: 176915
• Molecular Formular: C18H26O2
• Molecular Mass: 274.39784
• Monoisotopic Mass: 274.19328007
• SMILES: C1C(=O)CC2=C(C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C
• Canonical SMILES: O=C1CCC2=C(C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h14-17,20H,2-10H2,1H3/t14-,15-,16+,17+,18+/m1/s1
• InChIKey: BAZGVDKAIHZPOH-ZBRFXRBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-one
• IUPAC Traditional name: prenortestosterone
• Synonyms: 17β-Hydroxy-19-norandrost-5(10)-en-3-one; 17β-Hydroxyestr-5(10)-en-3-one; Estr-5(10)-en-17β-ol-3-one; NSC 37320; Prenortestosterone

Database IDs

• CAS Number: 1089-78-7
• PubChem SID: 164232825
• PubChem CID: 235672

CALCULATED PROPERTIES

• Acid pKa: 16.301239
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.661973
• LogD (pH = 7.4): 2.6619732
• Log P: 2.6619732
• Molar Refractivity: 79.7114 cm^3
• Polarizability: 31.416986 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane

DETAILS

Toronto Research Chemicals - P712760

Testosterone (T155000) derivative. Inhibits estrogen biosynthesis. A steroid ligand for the cytosol androgen receptor (AR) of rat prostate.

REFERENCES

• Ojasoo, T. et al.; J. Steroid Biochem. 27, 255 (1987)
• Schwarzel, W. et al.; Endrocrinology 92, 866 (1987)