(6E)-9-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

• ChemBase ID: 170160
• Molecular Formular: C18H27NO4
• Molecular Mass: 321.41128
• Monoisotopic Mass: 321.19400835
• SMILES: c1(c(ccc(c1)CNC(=O)CCCC/C=C/C(CO)C)O)OC
• Canonical SMILES: OCC(/C=C/CCCCC(=O)NCc1ccc(c(c1)OC)O)C
• InChI: InChI=1S/C18H27NO4/c1-14(13-20)7-5-3-4-6-8-18(22)19-12-15-9-10-16(21)17(11-15)23-2/h5,7,9-11,14,20-21H,3-4,6,8,12-13H2,1-2H3,(H,19,22)/b7-5+
• InChIKey: OCVIWAFGWPJVGZ-FNORWQNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E)-9-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• IUPAC Traditional name: (6E)-9-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• Synonyms: (6E)-9-Hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide; ω-Hydroxycapsaicin; 17-Hydroxy Capsaicin

Database IDs

• CAS Number: 69173-71-3
• PubChem SID: 164226070
• PubChem CID: 21581804

CALCULATED PROPERTIES

• Rotatable Bonds: 10
• Lipinski's Rule of Five: true
• Acid pKa: 9.928691
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.390928
• LogD (pH = 7.4): 2.3896694
• Log P: 2.3909447
• Molar Refractivity: 92.1691 cm^3
• Polarizability: 35.29277 Å^3
• Polar Surface Area: 78.79 Å^2

DETAILS

Toronto Research Chemicals - H825030

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)