(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-diol

• ChemBase ID: 170448
• Molecular Formular: C22H30O2
• Molecular Mass: 326.4724
• Monoisotopic Mass: 326.2245802
• SMILES: C1CC(C=C2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=C)([C@](CC2)(O)C#C)CC)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC(=C)[C@H]1[C@H]2CCC2=CC(CC[C@H]12)O
• InChI: InChI=1S/C22H30O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,16-20,23-24H,3-4,6-11,13H2,1H3/t16?,17-,18-,19-,20+,21-,22-/m0/s1
• InChIKey: ZMLDTNLDYRJTAZ-SITGORPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-diol
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-diol
• Synonyms: (17α)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yne-3,17-diol; 3(R,S)-Hydroxy Desogestrel

Database IDs

• CAS Number: 869627-85-0
• PubChem SID: 164226358
• PubChem CID: 71748977

CALCULATED PROPERTIES

• Acid pKa: 17.524948
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.1898313
• LogD (pH = 7.4): 3.1898315
• Log P: 3.1898315
• Molar Refractivity: 97.249 cm^3
• Polarizability: 38.000423 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H939000

A metabolite of Desogestrel.

REFERENCES

• Back, D., et al.: Br. J. Clin. Pharmacol., 26, 23 (1988)
• Wienkers, L., et al.: Drug Metab. Dispos., 1990, 24, 610 (1988)
• Bourrie, M., et al.: J. Pharmacol. Exp. Ther., 277, 321 (1988)
• Ono, S., et al.: Xenobiotica, 26, 681 (1988)