(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,8,14-trione

• ChemBase ID: 176075
• Molecular Formular: C19H22O3
• Molecular Mass: 298.37618
• Monoisotopic Mass: 298.15689456
• SMILES: C1=C[C@]2(C(=CC1=O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H22O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h5,7,9,12-14H,3-4,6,8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1
• InChIKey: BXPQXTJWPDQYMP-IEVKOWOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,8,14-trione
• IUPAC Traditional name: (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,8,14-trione
• Synonyms: Androsta-1,4-diene-3,6,17-trione; FCE 24204; 6-Oxo Boldione

Database IDs

• CAS Number: 72648-46-5
• PubChem SID: 164231985
• PubChem CID: 135516

CALCULATED PROPERTIES

• Acid pKa: 19.770311
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.2594912
• LogD (pH = 7.4): 3.2594912
• Log P: 3.2594912
• Molar Refractivity: 85.394 cm^3
• Polarizability: 32.54416 Å^3
• Polar Surface Area: 51.21 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 208-211°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O869900

A derivative of Exemestane (E957000), a new aromatase inhibitor.

REFERENCES

• Thompson, E., et al.: J. Biol. Chem., 249, 5364 (1974)
• Cole, P., et al.: J. Med. Chem., 33, 2933 (1974)
• Buzzetti, F., et al.: Steroids, 58, 527 (1974)