(1S,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,14-diol

• ChemBase ID: 173722
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)CC)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C21H26O2/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/h2,6,8,13,17-19,22-23H,3,5,7,9-12H2,1H3/t17-,18-,19+,20+,21+/m1/s1
• InChIKey: VDKWHNVDYOVIIX-MJCUULBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol
• Synonyms: (17α)-13-Ethyl-18,19-dinorpregna-1,3,5(10)-trien-20-yne-3,17-diol; 13-Ethyl-17α-ethynylgona-1,3,5(10)-triene-3,17β-diol; 18-Methyl Ethynyl Estradiol

Database IDs

• CAS Number: 14012-72-7
• PubChem SID: 164229632
• PubChem CID: 21114735

CALCULATED PROPERTIES

• Acid pKa: 10.327052
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.341915
• LogD (pH = 7.4): 4.341411
• Log P: 4.341922
• Molar Refractivity: 91.9755 cm^3
• Polarizability: 35.74056 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M304970

A Norgestrel (N689500) impurity. An estratriene derivative with estrogenic and ovulation inhibiting activity.

REFERENCES

• Rufer, C. et al.: Just. Lieb. Annal. Chem., 752, 1 (1971)
• Sopirak, A.M., et al.: Anal. Profiles Drug Subs., 4, 294 (1971)
• Dunson, T.R., et al.: Contraception, 48, 109 (1971)