Structure Database (LMSD)
Common Name
N-oleoyl phenylalanine
Systematic Name
N-(9Z-octadecenoyl)-phenylalanine
Synonyms
LM ID
LMFA08020092
Formula
Exact Mass
Calculate m/z
429.324294
Sum Composition
Status
Curated
3D model of N-oleoyl phenylalanine
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-Oleoyl-L-phenylalanine is an N-acyl amide.1 It increases the oxygen consumption rate (OCR) of mitochondria isolated from mouse brown adipose tissue in a Seahorse assay and decreases oligomycin-induced increases in the mitochondrial membrane potential in C2C12 cells, indicating mitochondrial uncoupling activity, when used at a concentration of 50 µM. N-Oleoyl-L-phenylalanine (30 mg/kg for eight days) reduces food intake and body weight of diet-induced obese mice.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
UWKNPULCJWBBDD-JRUKXMRZSA-N
InChi (Click to copy)
InChI=1S/C27H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26(29)28-25(27(30)31)23-24-20-17-16-18-21-24/h9-10,16-18,20-21,25H,2-8,11-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/b10-9-/t25-/m0/s1
SMILES (Click to copy)
C1(C=CC=CC=1)C[C@]([H])(NC(CCCCCCC/C=C\CCCCCCCC)=O)C(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
31
Rings
1
Aromatic Rings
1
Rotatable Bonds
19
Van der Waals Molecular Volume
473.93
Topological Polar Surface Area
66.40
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
7.12
Molar Refractivity
129.68
Admin
Created at
-
Updated at
20th Feb 2024