(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.02,7.011,15]heptadeca-1,6,16-trien-5-one

• ChemBase ID: 169624
• Molecular Formular: C21H24O2
• Molecular Mass: 308.41406
• Monoisotopic Mass: 308.17763001
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](C=C3)([C@](CC2)(O)C#C)CC)C1
• Canonical SMILES: CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@]2(O)C#C
• InChI: InChI=1S/C21H24O2/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/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
• InChIKey: BJJXHLWLUDYTGC-ANULTFPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6,16-trien-5-one
• IUPAC Traditional name: gestrinone
• Synonyms: (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one; 13-Ethyl-17α-ethynyl-17β-hydroxygona-4,9,11-trien-3-one; A 46745; Dimetriose; Dimetrose; Nemestran; R 2323; RU 2323; Tridomose; Gestrinone

Database IDs

• CAS Number: 16320-04-0
• PubChem SID: 162263756
• PubChem CID: 27812

CALCULATED PROPERTIES

• Acid pKa: 17.881264
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.8506377
• LogD (pH = 7.4): 2.8506377
• Log P: 2.8506377
• Molar Refractivity: 93.7255 cm^3
• Polarizability: 35.3689 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 150-152°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G368800

Steroidal antiestrogen, antiprogestogen, analog of Norgestrienone. Antigonadotropin.Controlled substance.

REFERENCES

• Azadian-Boulanger, G., et al.: Am. J. Obstet. Gynecol., 125, 1049 (1976)
• Thomas, E.J., et al.: Br. Med. J., 294, 272 (1976)
• Coutinho, E.M., et al.: Fertil. Steril., 49, 418 (1976)