(1S,2R,10R,11S,15S)-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 165601
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C=C2)[C@H]2[C@](CC1)(C(CC2)OC(=O)C)C
• Canonical SMILES: CC(=O)OC1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=CC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C20H26O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h3,5,11,15-19H,4,6-10H2,1-2H3/t15-,16+,17+,18-,19?,20-/m0/s1
• InChIKey: OGUASZAAVFYYIL-KOUBEUHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: 17β-Acetoxyestra-4,6-dien-3-one; 17β-Hydroxyestra-4,6-dien-3-one Acetate; 6-Dehydro-19-nortestosterone Acetate; Dehydronandrolone; 6-Dehydro Nandrolone Acetate

Database IDs

• CAS Number: 2590-41-2
• PubChem SID: 162259734
• PubChem CID: 46780581

CALCULATED PROPERTIES

• Acid pKa: 19.69217
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.14458
• LogD (pH = 7.4): 3.14458
• Log P: 3.14458
• Molar Refractivity: 90.2228 cm^3
• Polarizability: 35.00341 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 95-98°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D229125

Tibolone intermediate.

REFERENCES

• Schottler, C., et al.: Biochem. Pharmacol., 23, 2867 (1974)
• Joannou, G., et al.: Steroids, 61, 18 (1974)
• Shetty, G., et al.: Endocrinology, 143, 3385 (1974)