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

• ChemBase ID: 175653
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@](CC2)(O)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16?,17-,18-,19+,20+,21+/m1/s1
• InChIKey: WWYNJERNGUHSAO-XZCODKSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy(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,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy(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-18,19-dinorpregn-4-en-20-yn-3-one-d6; (+/-)-13-Ethyl-17α-ethynyl-17-hydroxygon-4-en-3-one-d6; (+/-)-Norgestrel-d6; DL-Norgestrel-d6; FH 122A-d6; Methylnorethindrone-d6; Monovar-d6; Neogest-d6; Ovrette-d6; Postinor-d6; SH 70850-d6; SH 850-d6; Wy 3707-d6; Norgestrel-d6 (major)

Database IDs

• PubChem SID: 164231563
• PubChem CID: 71751212

CALCULATED PROPERTIES

• Acid pKa: 17.90929
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6617966
• LogD (pH = 7.4): 3.6617966
• Log P: 3.6617966
• Molar Refractivity: 92.0255 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 240-242°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N689502

Labelled Norgestrel. It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.

REFERENCES

• Sopirak, A.M., et al.: Anal. Profiles Drug Subs., 4, 294 (1975)
• Dunson, T.R., et al.: Contraception, 48, 109 (1975)