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

• ChemBase ID: 170333
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](CC3OO)([C@](CC2)(O)CC#N)C)C1
• Canonical SMILES: OOC1C[C@@]2(C)[C@H]([C@H]3C1=C1CCC(=O)C=C1CC3)CC[C@@]2(O)CC#N
• InChI: InChI=1S/C20H25NO4/c1-19-11-17(25-24)18-14-5-3-13(22)10-12(14)2-4-15(18)16(19)6-7-20(19,23)8-9-21/h10,15-17,23-24H,2-8,11H2,1H3/t15-,16-,17?,19-,20+/m0/s1
• InChIKey: RLOFVNFCBUJNAR-NPZYAJIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(10S,11S,14R,15S)-17-hydroperoxy-14-hydroxy-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)-17-hydroperoxy-14-hydroxy-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-Hydroperoxy-17-hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 11β-Hydroperoxy Dienogest

Database IDs

• CAS Number: 106111-43-7
• PubChem SID: 164226243
• PubChem CID: 71748926

CALCULATED PROPERTIES

• Acid pKa: 11.707353
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.5313765
• LogD (pH = 7.4): 1.5313555
• Log P: 1.5313768
• Molar Refractivity: 93.0567 cm^3
• Polarizability: 36.03897 Å^3
• Polar Surface Area: 90.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >100°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H914685

Dienogest (D441870) impurity.

REFERENCES

• Hobe, G., et al.: Pharmazie, 41, 627 (1986)