(1S,2S,4R,7S,10R,11S,14R,15S)-4-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl acetate

• ChemBase ID: 158988
• Molecular Formular: C21H31BrO3
• Molecular Mass: 411.37304
• Monoisotopic Mass: 410.14565685
• SMILES: [C@@H]1(C(=O)C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)OC(=O)C)C)C)Br
• Canonical SMILES: CC(=O)O[C@@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C[C@@H](Br)C(=O)C2
• InChI: InChI=1S/C21H31BrO3/c1-12(23)25-19-7-6-15-14-5-4-13-10-18(24)17(22)11-21(13,3)16(14)8-9-20(15,19)2/h13-17,19H,4-11H2,1-3H3/t13-,14-,15-,16-,17+,19+,20-,21-/m0/s1
• InChIKey: KIYCCKUSMYHYMN-PMFAJICFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,7S,10R,11S,14R,15S)-4-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl acetate
• IUPAC Traditional name: (1S,2S,4R,7S,10R,11S,14R,15S)-4-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl acetate
• Synonyms: 17β-Acetoxy-2α-bromo-5α-androstan-3-one; 2α-Bromo-17β-hydroxy-5α-androstan-3-one Acetate; 17β-Acetoxy-2α-bromo-5α-androstanone

Database IDs

• CAS Number: 6173-35-9
• PubChem SID: 162253123
• PubChem CID: 71312765

CALCULATED PROPERTIES

• Acid pKa: 18.12433
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.5214043
• LogD (pH = 7.4): 4.5214043
• Log P: 4.5214043
• Molar Refractivity: 100.2813 cm^3
• Polarizability: 40.00624 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A164420

A steroid analog with inhibitive effects in progesterone synthesis and in dihydrotestosterone binding to receptor protein.

REFERENCES

• Sharp, R. et al.: Steroids 51, 441 (1988)
• Skinner, R. W. et al.: Steroids 25, 189 (1975).