(6E)-8-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

• ChemBase ID: 170158
• Molecular Formular: C18H27NO4
• Molecular Mass: 321.41128
• Monoisotopic Mass: 321.19400835
• SMILES: c1(c(ccc(c1)CNC(=O)CCCC/C=C/C(O)(C)C)O)OC
• Canonical SMILES: COc1cc(CNC(=O)CCCC/C=C/C(O)(C)C)ccc1O
• InChI: InChI=1S/C18H27NO4/c1-18(2,22)11-7-5-4-6-8-17(21)19-13-14-9-10-15(20)16(12-14)23-3/h7,9-12,20,22H,4-6,8,13H2,1-3H3,(H,19,21)/b11-7+
• InChIKey: OGBQQOBPAFILCJ-YRNVUSSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E)-8-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• IUPAC Traditional name: (6E)-8-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• Synonyms: (6E)-8-Hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide; 16-Hydroxy Capsaicin

Database IDs

• CAS Number: 112848-19-8
• PubChem SID: 164226068
• PubChem CID: 71748835

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.4344459
• LogD (pH = 7.4): 2.433187
• Log P: 2.4344623
• Molar Refractivity: 91.9995 cm^3
• Polarizability: 35.29277 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825025

A metabolite of Capsaicin (C175680).

REFERENCES

• Surh, Y., et al.: Food Chem. Toxicol., 34, 313 (1996)
• Bley, K., et al.: Expert. Opin. Investig. Drugs, 13, 1445 (1996)
• Reilly, C., et al.: Drug Metab. Rev., 38, 685 (1996)