Structure Database (LMSD)
Common Name
Macamide
Systematic Name
N-(9Z,12Z-octadecadienoyl) benzylamine
Synonyms
- N-benzyllinoleamide
3D model of Macamide
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
N-Benzyl linoleamide is an inhibitor of soluble epoxide hydrolase (sEH; IC50s = 0.155, 0.041, and 0.044 µM for the human, rat, and mouse enzymes, respectively).1 It is selective for sEH over fatty acid amide hydrolase (FAAH; IC50 = 10.8 µM for the human enzyme). N-Benzyl linoleamide also inhibits the production of NF-κB (IC50 = 8.80 µM) and activates nuclear factor erythroid 2-related factor 2 (Nrf2; EC50 = 35.24 µM in a transactivation assay) in Neuro2a murine neuroblastoma cells.2 It increases the paw withdrawal threshold in a mouse model of LPS-induced inflammatory pain when administered at a dose of 100 mg/kg.1
This information has been provided by Cayman Chemical
References
1. Singh, N., Barnych, B., Morisseau, C., et al. N‑Benzyl-linoleamide, a constituent of Lepidium meyenii (maca), is an orally bioavailable soluble epoxide hydrolase inhibitor that alleviates inflammatory pain. J. Nat. Prod. 83(12), 3689-3697 (2020).
2. Ticona, L.A., Pérez, V.T., Serban, A.M., et al. Design, synthesis and pharmacological evaluation of N-benzyl linoleamide analogues from Tropaeolum tuberosum as NF-κB inhibitors and Nrf2 activators. ChemistrySelect 5(38), 11825-11836 (2020).
References
Taxonomy Information
String Representations
InChiKey (Click to copy)
YJWLCIANOBCQGW-HZJYTTRNSA-N
InChi (Click to copy)
InChI=1S/C25H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-25(27)26-23-24-20-17-16-18-21-24/h6-7,9-10,16-18,20-21H,2-5,8,11-15,19,22-23H2,1H3,(H,26,27)/b7-6-,10-9-
SMILES (Click to copy)
C(C1C=CC=CC=1)NC(CCCCCCC/C=C\C/C=C\CCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
1
Aromatic Rings
1
Rotatable Bonds
16
Van der Waals Molecular Volume
421.75
Topological Polar Surface Area
29.10
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
7.12
Molar Refractivity
117.65
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Updated at
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