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

• ChemBase ID: 159385
• Molecular Formular: C25H33NO4
• Molecular Mass: 411.53382
• Monoisotopic Mass: 411.24095854
• SMILES: C1/C(=N\OC(=O)C)/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: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C)CCC1=C/C(=N/OC(=O)C)/CC[C@H]31
• InChI: InChI=1S/C25H33NO4/c1-5-24-13-11-21-20-10-8-19(26-30-17(4)28)15-18(20)7-9-22(21)23(24)12-14-25(24,6-2)29-16(3)27/h2,15,20-23H,5,7-14H2,1,3-4H3/b26-19+/t20?,21-,22-,23+,24+,25+/m1/s1
• InChIKey: JWLHCJCKDYVRNJ-FHBBRRDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2R,5E,10R,11S,14R,15S)-14-(acetyloxy)-15-ethyl-14-ethynyl(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-ylidene]amino acetate
• IUPAC Traditional name: [(1S,2R,5E,10R,11S,14R,15S)-14-(acetyloxy)-15-ethyl-14-ethynyl(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-ylidene]amino acetate
• Synonyms: (17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregna-1,3,5(10)-trien-20-yn-3-one O-Acetyloxime; N-Acetyl Norgestimate-d6

Database IDs

• CAS Number: 1263195-02-3
• PubChem SID: 162253520
• PubChem CID: 46780040

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.255023
• LogD (pH = 7.4): 4.2552915
• Log P: 4.255295
• Molar Refractivity: 114.1502 cm^3
• Polarizability: 44.782368 Å^3
• Polar Surface Area: 64.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Light Yellow Powder

DETAILS

Toronto Research Chemicals - A187282

Labelled intermediate of Norgestimate.

REFERENCES

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