2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxo(4,4,6-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-14-yl](2H2)acetonitrile

• ChemBase ID: 167105
• Molecular Formular: C20H25NO2
• Molecular Mass: 311.418
• Monoisotopic Mass: 311.18852905
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](CC3)([C@](CC2)(O)CC#N)C)C1
• Canonical SMILES: N#CC[C@]1(O)CC[C@@H]2[C@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@H]21
• InChI: InChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1
• InChIKey: AZFLJNIPTRTECV-FUMNGEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxo(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-14-yl](^2H₂)acetonitrile
• IUPAC Traditional name: 2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxo(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-14-yl](^2H₂)acetonitrile
• Synonyms: (17α)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile-d5; 17α-Cyanomethyl-17β-hydroxyestra-4, 9-dien-3-one-d5; Dienogestril-d5; Endometrion-d5; STS 557-d5; Dienogest-d5 (major)

Database IDs

• PubChem SID: 162261238
• PubChem CID: 71315979

CALCULATED PROPERTIES

• Acid pKa: 13.782009
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3128524
• LogD (pH = 7.4): 2.3128524
• Log P: 2.3128524
• Molar Refractivity: 90.191 cm^3
• Polarizability: 34.700165 Å^3
• Polar Surface Area: 61.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Beige to Yellow Solid
• Melting Point: 210-212°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D441872

Labelled derivative of 19-Nortestosterone. In combination with estrogen as oral contraceptive. Progestogen.

REFERENCES

• Hubner, M., et al.: Arzneim.-Forsch., 30, 401 (1980)
• Spona, J., et al.: Contraception, 56, 185 (1980)
• Foster, R.H., et al.: Drugs, 56, 825 (1980)