(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnona-6,8-dienamide

• ChemBase ID: 165616
• Molecular Formular: C18H25NO3
• Molecular Mass: 303.396
• Monoisotopic Mass: 303.18344367
• SMILES: c1(c(ccc(c1)CNC(=O)CCCC/C=C/C(=C)C)O)OC
• Canonical SMILES: COc1cc(CNC(=O)CCCC/C=C/C(=C)C)ccc1O
• InChI: InChI=1S/C18H25NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,20H,1,4-5,7,9,13H2,2-3H3,(H,19,21)/b8-6+
• InChIKey: LSIRKKJMETWUBA-SOFGYWHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnona-6,8-dienamide
• IUPAC Traditional name: (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnona-6,8-dienamide
• Synonyms: (6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6,8-nonadienamide; 16,17-Dehydro Capsaicin

Database IDs

• CAS Number: 509101-57-9
• PubChem SID: 162259749
• PubChem CID: 71315300

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.4020073
• LogD (pH = 7.4): 3.4007485
• Log P: 3.4020238
• Molar Refractivity: 90.0949 cm^3
• Polarizability: 34.430763 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229325

A dehydrogenated metabolite of Capsaicin (C175680).

REFERENCES

• Glinsukon, T., et al.: Toxicon, 18, 215 (1980)
• Obach, R., et al.: Drug Metab. Dispos., 29, 1599 (1980)
• Reilly, C., et al.: Toxicol. Sci., 73, 170 (1980)