(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyl-8-methylidene(13,13,14-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 170510
• Molecular Formular: C20H26O2
• Molecular Mass: 298.41924
• Monoisotopic Mass: 298.19328007
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2=C)[C@H]2[C@](CC1)([C@H](CC2)O)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)C(=C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C20H26O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16,18,22H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,18-,19+,20-/m0/s1
• InChIKey: NFDPYPMRHKQTDM-NHWXPXPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyl-8-methylidene(13,13,14-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyl-8-methylidene(13,13,14-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (17β)-17-Hydroxy-6-methyleneandrosta-1,4-dien-3-one-d3; Methylene Boldenone-d3; 17β-Hydroxy Exemestane-d3

Database IDs

• PubChem SID: 164226420
• PubChem CID: 71749001

CALCULATED PROPERTIES

• Acid pKa: 19.377699
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.30262
• LogD (pH = 7.4): 3.3026202
• Log P: 3.3026202
• Molar Refractivity: 89.8492 cm^3
• Polarizability: 34.62599 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: Pale Yellow Solid
• Melting Point: 68-72°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H942342

A labelled metabolite of Exemestane; exerts biological effects as an androgen.

REFERENCES

• Howell, A., et al.: Lancet, 365, 60 (2005)
• Goss, P., et al.: Clin. Cancer Res., 10, 5717 (2005)
• Buzdar, A., et al.: Lancet Oncol., 7, 633 (2005)
• Coates, A., et al.: J. Clin. Oncol., 25, 486 (2005)
• Jordan, V., et al.: Steroids, 72, 7 (2005)