(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

• ChemBase ID: 159753
• Molecular Formular: C26H37NO2
• Molecular Mass: 395.57748
• Monoisotopic Mass: 395.28242943
• SMILES: c1c(ccc(c1)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)O
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)Nc1ccc(cc1)O
• InChI: InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-
• InChIKey: IJBZOOZRAXHERC-DOFZRALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
• Synonyms: (5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)-5,8,11,14-eicosatetraenamide; (all-Z)-N-(4-Hydroxyphenyl)-5,8,11,14-eicosatetraenamide; AM 404

Database IDs

• CAS Number: 183718-77-6
• PubChem SID: 162253888
• PubChem CID: 6604822

CALCULATED PROPERTIES

• Acid pKa: 9.461591
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 7.71786
• LogD (pH = 7.4): 7.714177
• Log P: 7.7179074
• Molar Refractivity: 130.2122 cm^3
• Polarizability: 48.05595 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A575810

It is a metabolite of the well-known analgesic Paracetamol. AM404 inhibits endocannabinoid cellular uptake, binds weakly to CB1 and CB2 cannabinoid receptors, and is formed by fatty acid amide hydrolase (FAAH) in vivo.

REFERENCES

• Basile, S., et al.: Pain, 52, 217 (1993)
• Beltramo, M., et al.: Science, 277, 1094 (1993)
• Bisogno, T., et al.: J. Biol. Chem., 272, 3315 (1993)
• Nicholson, R., et al.: Brain Res., 978, 194 (1993)
• La Rana, G., et al.: J. Pharmacol. Exp. Ther., 317, 1365