(1S,2R,10S,11S,14S,15S)-15-ethyl-14-(2H)ethynyl-14-hydroxy-17-methylidene(2,4,4,6,8,8-2H6)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 168817
• Molecular Formular: C22H28O2
• Molecular Mass: 324.45652
• Monoisotopic Mass: 324.20893014
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=C)([C@](CC2)(O)C#C)CC
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC(=C)[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17?,18-,19-,20+,21-,22-/m0/s1
• InChIKey: GCKFUYQCUCGESZ-BHPIROGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S)-15-ethyl-14-(^2H)ethynyl-14-hydroxy-17-methylidene(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10S,11S,14S,15S)-15-ethyl-14-(^2H)ethynyl-14-hydroxy-17-methylidene(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (17α)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one-d7; 3-Ketodesogestrel-d7; 3-Oxodesogestrel-d7; Org-3236-d7; Implanon-d7; Etonogestrel-d7 (Major)

Database IDs

• PubChem SID: 162262949
• PubChem CID: 71316692

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6011698
• LogD (pH = 7.4): 3.6011698
• Log P: 3.6011698
• Molar Refractivity: 96.3516 cm^3
• Polarizability: 37.451656 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 17.993504

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 199-201°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E933627

A biologically active labelled metabolite of Desogestrel.

REFERENCES

• Croxatto, H.B., et al.: Hum. Reprod., 14, 976 (1999)
• Edwards, J.E., et al.: Brit. J. Fam. Plan., 24, 3 (1999)