(10S,11S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-diene-5,14-dione

• ChemBase ID: 168194
• Molecular Formular: C18H22O2
• Molecular Mass: 270.36608
• Monoisotopic Mass: 270.16197994
• SMILES: C1CC(=O)C=C2C1=C1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C
• Canonical SMILES: O=C1CCC2=C3CC[C@]4([C@H]([C@@H]3CCC2=C1)CCC4=O)C
• InChI: InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,15-16H,2-9H2,1H3/t15-,16+,18+/m1/s1
• InChIKey: BHTWZQKERRCPRZ-RYRKJORJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-diene-5,14-dione
• IUPAC Traditional name: (10S,11S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-diene-5,14-dione
• Synonyms: 19-Norandrosta-4,9-diene-3,17-dione; Trena; (-)-Estra-4,9-diene-3,17-dione; (+/-)-19-Norandrosta-4,9-dien-3,17-dione; (+/-)-Estra-4,9-diene-3,17-dione(Mixture of 2 Enantiomers)

Database IDs

• CAS Number: 5173-46-6; 13885-20-6
• PubChem SID: 162262326
• PubChem CID: 9835169

CALCULATED PROPERTIES

• Acid pKa: 19.007645
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.1796665
• LogD (pH = 7.4): 3.1796665
• Log P: 3.1796665
• Molar Refractivity: 79.7158 cm^3
• Polarizability: 30.629208 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Beige Solid
• Melting Point: 131-134°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E668545

The mixture of two enantiomers of Estra-4,9-diene-3,17-dione (E668550). It is used in the synthesis of (±)-Estrone (E889050) and (±)-Adrenosterone (A305600). A steroid with antiglucocorticoid activity.

Toronto Research Chemicals - E668550

A potential metabolite of STS 557 (Dienogest)(D441870). A steroid with antiglucocorticoid activity.

REFERENCES

• Kloosterboer, H., et al.: J. Steroid Biochem., 31, 567 (1988)
• Kloosterboer, H., et al.: J. Steroid Biochem., 31, 567 (1988)