(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadec-3-en-5-one

• ChemBase ID: 172749
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: C1=C([C@]2([C@H](CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C)C
• Canonical SMILES: O=C1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C(=C1)C)C)CC[C@]1([C@H]3CC[C@@H]1O)C
• InChI: InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1
• InChIKey: ANJQEDFWRSLVBR-VHUDCFPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-5-one
• IUPAC Traditional name: methenolone
• Synonyms: (5α,17β)-17-Hydroxy-1-methylandrost-1-en-3-one; 17β-Hydroxy-1-methyl-5α-androst-1-en-3-one; 1-Methyl-5α-androst-1-en-17β-ol-3-one; 1-Methyl-Δ1-androsten-17β-ol-3-one; Metenolone; Methenolon; Methenolone

Database IDs

• CAS Number: 153-00-4
• PubChem SID: 164228659
• PubChem CID: 3037705

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6524425
• LogD (pH = 7.4): 3.6524425
• Log P: 3.6524425
• Molar Refractivity: 88.9784 cm^3
• Polarizability: 35.103523 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M226240

Methenolone is an anabolic steroid. This is a controlled substance.

REFERENCES

• Schiffer, M., et al.: J. Clin. Invest., 108, 807 (2001)
• Okuyama, S., et al.: Clin. Nephrol., 68, 412 (2001)
• Sjoqvist, F., et al.: Lancet, 371, 1872 (2001)