(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-3-en-5-one

• ChemBase ID: 178178
• Molecular Formular: C19H28O2
• Molecular Mass: 288.42442
• Monoisotopic Mass: 288.20893014
• SMILES: C1=C[C@]2(C(CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H28O2/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/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12?,14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: OKJCFMUGMSVJBG-QHDNXLQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-5-one
• Synonyms: (5α,17β)-17-Ηydroxyandrost-1-en-3-one; 17β-Hydroxy-5α-androst-1-en-3-one; 1-Testosterone; 5α-Androst-1-en-17β-ol-3-one; NSC 121140; NSC 39366; Δ1-Testosterone

Database IDs

• CAS Number: 65-06-5
• PubChem SID: 164234088
• PubChem CID: 11289222

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.409081
• LogD (pH = 7.4): 3.4090812
• Log P: 3.4090812
• Molar Refractivity: 84.6964 cm^3
• Polarizability: 33.260063 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 157-159°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - T155010

Testosterone (T155000) derivative. It is a potent androgen with anabolic properties. Since the begining of the year 2005, the use of steroid precursors (prohormones) is illegal in the United States. Controlled substance.

REFERENCES

• Liao, S., et al.: J. Biol. Chem., 248, 6154 (1973)
• Saartok, T., et al.: Endocrinology, 114, 2100 (1973)
• Sugawara, T., et al.: J. Biol. Chem., 278, 42487 (1973)