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

• ChemBase ID: 168561
• Molecular Formular: C20H34O2
• Molecular Mass: 306.48276
• Monoisotopic Mass: 306.25588033
• SMILES: C1C[C@H](C[C@@H]2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)CC)C)O
• Canonical SMILES: CC[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/C20H34O2/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/h13-18,21-22H,3-12H2,1-2H3/t13-,14-,15+,16-,17-,18+,19+,20+/m1/s1
• InChIKey: GUBNWXDDDXQJOQ-VIVHBNLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R,7R,10R,11S,14S,15S)-14-ethyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: (1R,2S,5R,7R,10R,11S,14S,15S)-14-ethyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• Synonyms: (3α,5β,17α)-19-Norpregnane-3,17-diol; 19-Nor-5β,17α-pregnane-3α,17-diol; 17α-Ethyl-5β-estrane-3α,17β-diol

Database IDs

• CAS Number: 31658-50-1
• PubChem SID: 162262693
• PubChem CID: 12133281

CALCULATED PROPERTIES

• Acid pKa: 18.30947
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.706808
• LogD (pH = 7.4): 3.7068088
• Log P: 3.7068088
• Molar Refractivity: 89.3183 cm^3
• Polarizability: 35.891087 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E917825

17α-Ethyl-5β-estrane-3α,17β-diol is metabolite of the anabolic steroid and illegal growth promoters Norethandrolone (N675000) and Ethylestrenol (E917830). 17α-Ethyl-5β-estrane-3α,17β-diol is a useful biological markers for detecting abuse of these growth

REFERENCES

• Van Puymbroeck, M. et al.: J. Chrom. B Biomed. Sci. Appl., 728, 217 (1999)
• Fragkaki, A.G. et al.: J. Steroid Biochem. Mol. Biol., 115, 44 (1999)