2-[(10S,11S,14R,15S,17S)-14,17-dihydroxy-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-14-yl]acetonitrile

• ChemBase ID: 170332
• Molecular Formular: C20H25NO3
• Molecular Mass: 327.4174
• Monoisotopic Mass: 327.18344367
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](C[C@@H]3O)([C@](CC2)(O)CC#N)C)C1
• Canonical SMILES: N#CC[C@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)C1=C3CCC(=O)C=C3CC[C@@H]21
• InChI: InChI=1S/C20H25NO3/c1-19-11-17(23)18-14-5-3-13(22)10-12(14)2-4-15(18)16(19)6-7-20(19,24)8-9-21/h10,15-17,23-24H,2-8,11H2,1H3/t15-,16-,17-,19-,20+/m0/s1
• InChIKey: QVHMVYURUMVWSF-VDWQKOAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(10S,11S,14R,15S,17S)-14,17-dihydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-14-yl]acetonitrile
• IUPAC Traditional name: 2-[(10S,11S,14R,15S,17S)-14,17-dihydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-14-yl]acetonitrile
• Synonyms: (11β,17α)-11,17-Dihydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 11β-Hydroxy-STS 557; 17β-Dihydroxyestra-4,9-dien-3-one 17α-Cyanomethyl-11β; STS 749; 11β-Hydroxy Dienogest

Database IDs

• CAS Number: 86153-39-1
• PubChem SID: 164226242
• PubChem CID: 71748925

CALCULATED PROPERTIES

• Acid pKa: 13.710831
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.0820414
• LogD (pH = 7.4): 1.0820413
• Log P: 1.0820414
• Molar Refractivity: 91.7065 cm^3
• Polarizability: 35.327488 Å^3
• Polar Surface Area: 81.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-white to Yellow Solid
• Melting Point: 96-108°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H905400

11β-Hydroxy Dienogest is a metabolite of Dienogest (D441870).

REFERENCES

• Oettel, M. et al.: Pharmazie 541, 48 (1993)
• Schubert, K. et al.: Studies in Organic Chemistry 20, 143 (1985).