AM404   Click here for help

GtoPdb Ligand ID: 12556

Synonyms: AM-404 | N-arachidonoylaminophenol
Compound class: Synthetic organic
Comment: A bioactive metabolite of paracetamol that is proposed to mediate the central antinociceptive effects of the drug [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 16
Topological polar surface area 49.33
Molecular weight 395.58
XLogP 8.74
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)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-
InChI Key IJBZOOZRAXHERC-DOFZRALJSA-N
References
1. Mallet C, Desmeules J, Pegahi R, Eschalier A. (2023)
An Updated Review on the Metabolite (AM404)-Mediated Central Mechanism of Action of Paracetamol (Acetaminophen): Experimental Evidence and Potential Clinical Impact.
J Pain Res, 16: 1081-1094. [PMID:37016715]
2. Nakagawa F, Higashi S, Ando E, Ohsumi T, Watanabe S, Takeuchi H. (2020)
Modification of TRPV4 activity by acetaminophen.
Heliyon, 6 (1): e03301. [PMID:32051870]