(1S,2R,4Z,10R,11S,14S,15S)-14-[(1,2-13C2)ethynyl]-14-hydroxy-4-[hydroxy(13C)methylidene]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 170799
• Molecular Formular: C22H28O3
• Molecular Mass: 343.43388451
• Monoisotopic Mass: 343.21390927
• SMILES: C\1(=[13CH]/O)/C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)[13C]#[13CH])C)C
• Canonical SMILES: O/[13CH]=C\1/C[C@@]2(C)C(=CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(O)[13C]#[13CH])C
• InChI: InChI=1S/C22H28O3/c1-4-22(25)10-8-18-16-6-5-15-11-19(24)14(13-23)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,23,25H,5-10,12H2,2-3H3/b14-13-/t16-,17+,18+,20+,21+,22+/m1/s1/i1+1,4+1,13+1
• InChIKey: FYEOMZSZJFOTGQ-XAVPDDTPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4Z,10R,11S,14S,15S)-14-[(1,2-^1^3C₂)ethynyl]-14-hydroxy-4-[hydroxy(^1^3C)methylidene]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,4Z,10R,11S,14S,15S)-14-[(1,2-^1^3C₂)ethynyl]-14-hydroxy-4-[hydroxy(^1^3C)methylidene]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (17α)-17-Hydroxy-2-(hydroxymethylene)-pregn-4-en-20-yn-3-one-13C3; 17-Ethynyl-2-(hydroxymethylene)-testosterone-13C3; 2-Hydroxymethylene Ethisterone-13C3

Database IDs

• PubChem SID: 164226709
• PubChem CID: 71749137

CALCULATED PROPERTIES

• Acid pKa: 8.490759
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.377727
• LogD (pH = 7.4): 3.3442984
• Log P: 3.3781703
• Molar Refractivity: 98.2552 cm^3
• Polarizability: 38.063484 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H946702

A labelled derivative of Danazol (D145000).

REFERENCES

• Manson, A.J., et al.: J. Med. Chem., 6, 1 (1963)
• Jordan, V.C., et al.: Endocrinology, 124, 1717 (1963)