(1S,2R,5Z,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-ol

• ChemBase ID: 166119
• Molecular Formular: C21H29NO2
• Molecular Mass: 327.46046
• Monoisotopic Mass: 327.21982917
• SMILES: C1/C(=N/O)/C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)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(O)C#C)CC
• InChI: InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/b22-15-/t16?,17-,18-,19+,20+,21+/m1/s1
• InChIKey: ISHXLNHNDMZNMC-BBBXPMLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5Z,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-ol
• IUPAC Traditional name: (1S,2R,5Z,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-ol
• Synonyms: (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one-d6 Oxime; 17-Deacetylnorgestimate-d6; 18-Methylnorethindrone-d6 Oxime; BRN 4202099-d6; D-Norgestrel-d6 3-Oxime; Levonorgestrel-d6 3-Oxime; RWJ 10553-d6; Norelgestromin-d6; 17-Desacetyl Norgestimate-d6 (Major)

Database IDs

• PubChem SID: 162260252
• PubChem CID: 71315574

CALCULATED PROPERTIES

• Acid pKa: 11.466128
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6694894
• LogD (pH = 7.4): 3.6712167
• Log P: 3.6712763
• Molar Refractivity: 95.8472 cm^3
• Polarizability: 37.191574 Å^3
• Polar Surface Area: 52.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 182-186°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288702

A labelled metabolite of Norgestimate.

REFERENCES

• Phillips, A., et al.: Steroids, 55, 373 (1990)