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

• ChemBase ID: 167706
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1C(=O)C[C@H]2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@](CC2)(C#C)O)C
• 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]1CCC(=O)C2
• InChI: InChI=1S/C20H28O2/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/h1,13,15-18,22H,4-12H2,2H3/t13-,15-,16+,17+,18-,19-,20-/m0/s1
• InChIKey: OMGILQMNIZWNOK-XDQPPUBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,7S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: (1R,2S,7S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• Synonyms: 17α-Ethynyl-17β-hydroxy-5α-estran-3-one; 17α-Ethynyl-5α-estran-17β-ol-3-one; 17β-Hydroxy-17α-ethynyl-5α-estran-3-one; 17β-Hydroxy-19-nor-5α,17α-pregn-20-yn-3-one; 5α-Dihydronorethindrone; 5α-Dihydronorethisterone; NSC 85401; STS 737; 4,5α-Dihydronorethisterone

Database IDs

• CAS Number: 52-79-9
• PubChem SID: 162261839
• PubChem CID: 63023

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.2630622
• LogD (pH = 7.4): 3.2630622
• Log P: 3.2630622
• Molar Refractivity: 86.5978 cm^3
• Polarizability: 34.243923 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D449510

Derivative of the synthetic anabolic steroid Norethandrolone (N675000).

REFERENCES

• Garcia-Becerra, R. et al.: J. Steroid Biochem. Mol. Biol. 99, 108 (2006)
• Garcia-Becerra, R. et al.: J. Steroid Biochem. Mol. Biol. 91, 27 (2006)
• Blom, M. et al: Drug Metab. Dispos. 29, 976 (2001)