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

• ChemBase ID: 171372
• Molecular Formular: C21H30O2
• Molecular Mass: 315.45435484
• Monoisotopic Mass: 315.22793504
• SMILES: C1[C@H](CC2=C(C1)[C@@H]1[C@@H]([C@H](C2)[13CH3])[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)O
• 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=C1CC[C@H](C2)O
• InChI: InChI=1S/C21H30O2/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/h1,13,15,17-19,22-23H,5-12H2,2-3H3/t13-,15+,17+,18-,19+,20-,21-/m0/s1/i2+1
• InChIKey: YLEUWNOTNJZCBN-SOQGJWNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,9S,10R,11S,14R,15S)-14-ethynyl-9-(^1^3C,^2H₃)methyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-ene-5,14-diol
• IUPAC Traditional name: (1S,5R,9S,10R,11S,14R,15S)-14-ethynyl-9-(^1^3C,^2H₃)methyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-ene-5,14-diol
• Synonyms: (3α,7α,17α)-3,17-Dihydroxy-7-(methyl-13C,d3)-19-norpregn-5(10)-en-20-yl-3-one; (3α,7α,17α)-7-(Methyl-13C,d3)-19-norpregn-5(10)-en-20-yne-3,17-diol; Org 4094-13C,d3; 3α-Hydroxy Tibolone-13C,d3

Database IDs

• PubChem SID: 164227282
• PubChem CID: 71749375

CALCULATED PROPERTIES

• Acid pKa: 17.594913
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.8933432
• LogD (pH = 7.4): 2.8933432
• Log P: 2.8933432
• Molar Refractivity: 92.7579 cm^3
• Polarizability: 36.3952 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 36-39°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H964252

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

REFERENCES

• Belman, S., et al.: Cancer Res., 32, 450 (1972)
• Shirahashi, H., et al.: Chem. Pharm. Bull., 41, 1664 (1972)
• Hoyte, R., et al.: Steroids, 58, 13 (1972)
• Sandker, G., et al.: Xenobiotica, 24, 143 (1972)
• Colombo, D., et al.: Eur. J. Med. Chem., 40, 69 (20