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

• ChemBase ID: 168269
• Molecular Formular: C18H30O2
• Molecular Mass: 278.4296
• Monoisotopic Mass: 278.2245802
• SMILES: C1C[C@@H](C[C@H]2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)O
• Canonical SMILES: O[C@H]1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H30O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-17,19-20H,2-10H2,1H3/t11-,12-,13-,14+,15+,16-,17-,18-/m0/s1
• InChIKey: QNKATSBSLLYTMH-WTCPTMCSSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1816-75-7
• PubChem SID: 162262401
• PubChem CID: 9814225

CALCULATED PROPERTIES

• Acid pKa: 18.30947
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.9037097
• LogD (pH = 7.4): 2.9037097
• Log P: 2.9037097
• Molar Refractivity: 80.1561 cm^3
• Polarizability: 32.204803 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E888915

5α-Estrane-3β,17β-diol is a metabolite of 17β-Nandrolone (N315000). 5α-Estrane-3β,17β-diol could be used as a biomarker for detecting nandrolone abuse in cattle.

REFERENCES

• Dervilly-Pinel, G. et al.: J. Steroid Biochem. Mol. Biol., 126, 65 (2011)
• Roig, M. et al.: Anal. Chim. Acta, 586, 184 (2011)