(1S,9S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9-(13C,2H3)methyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one

• ChemBase ID: 178631
• Molecular Formular: C21H28O2
• Molecular Mass: 313.43847484
• Monoisotopic Mass: 313.21228497
• SMILES: C1C(=O)CC2=C(C1)[C@@H]1[C@@H]([C@H](C2)[13CH3])[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H]([13CH3])CC2=C1CCC(=O)C2
• InChI: InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17+,18-,19+,20-,21-/m0/s1/i2+1
• InChIKey: WZDGZWOAQTVYBX-RQQVRZPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9-(^1^3C,^2H₃)methyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-one
• IUPAC Traditional name: (1S,9S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9-(^1^3C,^2H₃)methyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-one
• Synonyms: (7α,17α)-17-Hydroxy-7-(methyl-13C,d3)-19-norpregn-5(10)-en-20-yn-3-one; 7α-(Methyl-13C,d3)-5,10-norethindrone; 7α-(Methyl-13C,d3)-17α-ethynyl-17β-hydroxy-5(10)-estren-3-one; Livial-13C,d3; Liviella-13C,d3; Org OD 14-13C,d3; Tibolone-13C,d3

Database IDs

• PubChem SID: 164234541
• PubChem CID: 71752564

CALCULATED PROPERTIES

• Acid pKa: 16.26591
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1008441
• LogD (pH = 7.4): 3.1008441
• Log P: 3.1008441
• Molar Refractivity: 91.7298 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 161-164°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T437502

A synthetic steroid with weak estrogenic, androgenic and progestogenic activity. A pharamceutical used in the treatment of menopausal syndrome.

REFERENCES

• de Visser, J., et al.: Arzneim.-Forsch., 34, 1010 (1984)
• Geusens, P., et al.: Maturitas Suppl, 1, 1 (1987)