(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)(2,4,4,6,8,8-2H6)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 175651
• Molecular Formular: C23H31NO3
• Molecular Mass: 369.49714
• Monoisotopic Mass: 369.23039386
• SMILES: C1/C(=N\O)/C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(OC(=O)C)C#C)CC
• Canonical SMILES: O/N=C/1\CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)OC(=O)C)CC
• InChI: InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18?,19-,20-,21+,22+,23+/m1/s1
• InChIKey: KIQQMECNKUGGKA-OQSQNPJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-Oxime-d6; Dexnorgestrel Acetime-d6; D-138-d6; ORF-10131-d6; Norgestimate-d6 (major)

Database IDs

• PubChem SID: 164231561
• PubChem CID: 46782587

CALCULATED PROPERTIES

• Acid pKa: 11.466128
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.1106176
• LogD (pH = 7.4): 4.1123424
• Log P: 4.112402
• Molar Refractivity: 104.9987 cm^3
• Polarizability: 41.020058 Å^3
• Polar Surface Area: 58.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 60-65°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N686002

Progestogen. In combination with estrogen as oral contraceptive.A representative lot was 4.5% d4, 17.2% d5, 43.3% d6, 30.2% d7, 4.8% d8 with no detectable d0.

REFERENCES

• Hahn, D.W., et al.: Contraception, 16, 541 (1977)
• Weintraub, H.S., et al.: J. Pharm. Sci., 67, 1406 (1977)