(1S,2R,13R,14S,18S)-17-[(1,2-13C2)ethynyl]-2,18-dimethyl(5-13C)-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol

• ChemBase ID: 165364
• Molecular Formular: C22H27NO2
• Molecular Mass: 340.43324451
• Monoisotopic Mass: 340.21424362
• SMILES: c12c(C=C3[C@](C1)([C@@H]1[C@@H](CC3)[C@H]3[C@](CC1)(C(CC3)(O)[13C]#[13CH])C)C)on[13cH]2
• Canonical SMILES: [13CH]#[13C]C1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=Cc3c(C[C@]12C)[13cH]no3
• InChI: InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22?/m1/s1/i1+1,4+1,13+1
• InChIKey: POZRVZJJTULAOH-HDSDGRIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,13R,14S,18S)-17-[(1,2-^1^3C₂)ethynyl]-2,18-dimethyl(5-^1^3C)-7-oxa-6-azapentacyclo[11.7.0.0^2,^1^0.0^4,^8.0^1^4,^1^8]icosa-4(8),5,9-trien-17-ol
• IUPAC Traditional name: (1S,2R,13R,14S,18S)-17-[(1,2-^1^3C₂)ethynyl]-2,18-dimethyl(5-^1^3C)-7-oxa-6-azapentacyclo[11.7.0.0^2,^1^0.0^4,^8.0^1^4,^1^8]icosa-4(8),5,9-trien-17-ol
• Synonyms: (17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol-13C3; 17α-Ethynyl-17β-hydroxy-4-androsteno[2,3-d]isoxazole-13C3; Win-17757-13C3; Bonzol-13C3; Cyclomen-13C3; Danatrol-13C3; Danocrine-13C3; Danol-13C3; Danazol-13C3

Database IDs

• PubChem SID: 162259497
• PubChem CID: 71315167

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4620798
• LogD (pH = 7.4): 3.4620821
• Log P: 3.4620821
• Molar Refractivity: 98.5352 cm^3
• Polarizability: 37.660843 Å^3
• Polar Surface Area: 46.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol
• Apperance: White to Off-White Solid
• Melting Point: 215-2170C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D145002

An isotopically labelled analog of Danazol, an anterior pituitary supressant. Anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

REFERENCES

• Ahn, Y.S., et al.: N. Engl. J. Med., 308, 1396 (1983)