(1R,2R,9S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9-(13C,2H3)methyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 178633
• Molecular Formular: C21H28O2
• Molecular Mass: 313.43847484
• Monoisotopic Mass: 313.21228497
• SMILES: C1C(=O)C=C2[C@H](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=CC(=O)CC[C@H]12
• 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/h1,12-13,16-19,23H,5-11H2,2-3H3/t13-,16-,17+,18-,19+,20-,21-/m0/s1/i2+1
• InChIKey: WAOKMNBZWBGYIK-OFFIHOOLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,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-6-en-5-one
• IUPAC Traditional name: (1R,2R,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-6-en-5-one
• Synonyms: (7α,17α)-17-Hydroxy-7-(methyl-13C,d3)-19-norpregn-4-en-20-yn-3-one; 17α-Ethynyl-17-hydroxy-7α-(methyl-13C,d3)-4-estren-3-one; 7α-Methylnorethindrone-13C,d3; NSC 142228-13C,d3; Org-OM 38-13C,d3; Δ4-Tibolone-13C,d3

Database IDs

• PubChem SID: 164234543
• PubChem CID: 71752565

CALCULATED PROPERTIES

• Acid pKa: 17.594927
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.504247
• LogD (pH = 7.4): 3.504247
• Log P: 3.504247
• Molar Refractivity: 91.9731 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 Solid
• Melting Point: 188-190°C`

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T437507

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

• Clarkson, T., et al.: J. Clin. Endocrinol. Metab., 86, 5396 (2001)
• Landgren, M., et al.: Maturitas, 50, 222 (2001)
• Wang, M., et al.: Steroids, 71, 343 (2001)
• Verheul, H., et al.: Drug Metab. Dispos., 35, 1105 (2001)