(1R,2S,5S,7S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-diol

• ChemBase ID: 178391
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: C1[C@@H](C[C@H]2[C@H](C1)[C@@H]1[C@@H](CC2)[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]2CC[C@@H]2[C@@H]1CC[C@@H](C2)O
• InChI: InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,13-18,21-22H,4-12H2,2H3/t13-,14-,15-,16+,17+,18-,19-,20-/m0/s1
• InChIKey: DPDZKJQFRFZZCW-WSIJOFGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,7S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: (1R,2S,5S,7S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• Synonyms: (3β,5α,17α)-19-Norpregn-20-yne-3,17-diol; 19-Nor-5α,17α-pregn-20-yne-3β,17-diol; 17α-Ethynyl-5α-estrane-3β,17β-diol; 17α-Ethynyl-5α-oestrane-3β,17β-diol; 3β,5α-Tetrahydronorethisterone

Database IDs

• CAS Number: 6424-05-1
• PubChem SID: 164234301
• PubChem CID: 10402682

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.0555613
• LogD (pH = 7.4): 3.0555615
• Log P: 3.0555615
• Molar Refractivity: 87.6259 cm^3
• Polarizability: 34.79152 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 17.594933

DETAILS

Toronto Research Chemicals - T294140

A 3β-metabolite of progesterone receptor agonist Norethindrone (N676000) that acts as a estrogen receptor agonist in osteoblastic cells. It also has novel nongenomic endothelium-independent vasorelaxing effects.

REFERENCES

• Lemus, A.E. et al.: J. Endocrinol., 200, 199 (2009)
• Perusquia, M. et al.: Eur. J. Pharmacol., 475, 161 (2009)
• Blom, M.J. et al.: Drug Metab. Disp., 29, 976 (2009)