(1S,2R,8S,10R,11S,15S)-8-bromo-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 162747
• Molecular Formular: C19H25BrO2
• Molecular Mass: 365.3046
• Monoisotopic Mass: 364.10379204
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2Br)[C@H]2[C@](CC1)(C(=O)CC2)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](Br)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H25BrO2/c1-18-7-5-11(21)9-15(18)16(20)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16H,3-8,10H2,1-2H3/t12-,13-,14-,16-,18+,19-/m0/s1
• InChIKey: HAWQRBIGKRAICT-BMSLSITRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,15S)-8-bromo-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: (1S,2R,8S,10R,11S,15S)-8-bromo-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• Synonyms: (6α)-6-Bromoandrost-4-ene-3,17-dione; 6α-Bromo Androstenedione

Database IDs

• CAS Number: 61145-67-3
• PubChem SID: 162256882
• PubChem CID: 53867647

CALCULATED PROPERTIES

• Acid pKa: 16.91925
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.238227
• LogD (pH = 7.4): 4.238227
• Log P: 4.238227
• Molar Refractivity: 91.1575 cm^3
• Polarizability: 35.3626 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 171-174°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B679700

Androstenedione (A637550) analog, an aromatase inhibitor.

REFERENCES

• Marsh, D.A., et al.: J. Med. Chem., 28, 788 (1985)