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

• ChemBase ID: 168298
• Molecular Formular: C21H28O2
• Molecular Mass: 314.43112968
• Monoisotopic Mass: 314.21563981
• SMILES: C1C(=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: [13CH]#[13C][C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1/i1+1,4+1
• InChIKey: CHNXZKVNWQUJIB-QBZTVGGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-[(1,2-^1^3C₂)ethynyl]-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14S,15S)-14-[(1,2-^1^3C₂)ethynyl]-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 17α-Hydroxypregn-4-en-20-yn-3-one-13C2; 17α-Ethynyltestosterone-13C2; Ethinone-13C2; Gestoral-13C2; Lucorteum Oral-13C2; Lutocyclol-13C2; Nalutoral-13C2; Nugestoral-13C2; Pranone-13C2; Pregnin-13C2; Prodoxan-13C2; Progestab-13C2; Ethisterone-13C2

Database IDs

• PubChem SID: 162262430
• PubChem CID: 71316502

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.517275
• LogD (pH = 7.4): 3.517275
• Log P: 3.517275
• Molar Refractivity: 91.8996 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Off-White Powder
• Melting Point: 272-275°C

DETAILS

Toronto Research Chemicals - E890447

A labelled synthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone.

REFERENCES

• Chung, B., et al.: J. Anal. Toxicol., 14, 91 (1990)
• Schanzer, W., et al.: J. Steroid. Biochem. Mol. Biol., 57, 363 (1990)
• Chan, G., et al.: Am. J. Hematol., 71, 166 (1990)
• Szegvari, D., et al.: Anal. Bioanal. Chem., 375, 713 (2003)