(1S,2S,10R,14S)-14-(hydroxymethyl)-2,14-dimethyl(4,6,8,8-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,11(15)-trien-5-one

• ChemBase ID: 170863
• Molecular Formular: C20H26O2
• Molecular Mass: 298.41924
• Monoisotopic Mass: 298.19328007
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2CCC2=C1CC[C@@]2(CO)C)C
• Canonical SMILES: OC[C@@]1(C)CCC2=C1CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C20H26O2/c1-19(12-21)9-8-16-15-4-3-13-11-14(22)7-10-20(13,2)18(15)6-5-17(16)19/h7,10-11,15,18,21H,3-6,8-9,12H2,1-2H3/t15-,18-,19+,20-/m0/s1
• InChIKey: GCYZSDGHIVBKJR-QLIIJSOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10R,14S)-14-(hydroxymethyl)-2,14-dimethyl(4,6,8,8-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,11(15)-trien-5-one
• IUPAC Traditional name: (1S,2S,10R,14S)-14-(hydroxymethyl)-2,14-dimethyl(4,6,8,8-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,11(15)-trien-5-one
• Synonyms: (17α)-17-(Hydroxymethyl)-17-methyl-18-norandrosta-1,4,13-trien-3-one-d4; 17α-Hydroxymethyl-17β-methyl-18-norandrosta-1,4,13-trien-3-one-d4

Database IDs

• PubChem SID: 164226773
• PubChem CID: 71749166

CALCULATED PROPERTIES

• Acid pKa: 18.387472
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1510684
• LogD (pH = 7.4): 3.1510684
• Log P: 3.1510684
• Molar Refractivity: 90.9143 cm^3
• Polarizability: 34.62599 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H947967

Labelled analogue of 17α-Hydroxymethyl-17β-methyl-18-norandrosta-1,4,13-trien-3-one, a urinary metabolite of the human doping Methandienone (Methandrostenolone, M226000).

REFERENCES

• Lootens, L. et al.: Clin. Chem., 55, 1783 (2009)