Structure Database (LMSD)
Common Name
Palmitoyl Serinol
Systematic Name
N-(1,3-dihydroxypropan-2-yl)hexadecanamide
Synonyms
LM ID
LMFA08020197
Formula
Exact Mass
Calculate m/z
329.292994
Sum Composition
Status
Curated
3D model of Palmitoyl Serinol
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
Palmitoyl serinol is a derivative of 2-palmitoyl glycerol (2-PG), an endogenous fatty acid ester that potentiates the signaling and in vivo activity induced by the endocannabinoid 2-arachidonoyl glycerol (2-AG).1,2,3 It is a metabolite of human commensal bacteria and an agonist of GPR119, increasing cAMP levels in HEK293 cells expressing GPR119 (EC50 = 9 µM).4 Palmitoyl serinol (25 µM) reduces IL-4-induced decreases in the levels of long-chain fatty acid-containing ceramides in IL-4-stimulated HaCaT keratinocytes, an effect that can be blocked by the cannabinoid receptor 1 (CB1) antagonist AM-251.5 It also binds to PKCζ and induces apoptosis in F-11 neuroblastoma cells, an effect that can be blocked by the PKCζ inhibitor Gö 6983 .6
This information has been provided by Cayman Chemical
References
1. Bieberich, E., Kawaguchi, T., and Yu, R.K. N-acylated serinol is a novel ceramide mimic inducing apoptosis in neuroblastoma cells. The Journal of Biological Chemisty 275(1), 177-181 (2000).
4. Dinh, T.P., Freund, T.F., and Piomelli, D. A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation. Chem. Phys. Lipids 121(1-2), 149-158 (2002).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Escherichia coli
(#562)
Gammaproteobacteria
(#1236)
Commensal bacteria make GPCR ligands that mimic human signalling molecules.,
Nature, 2017
Nature, 2017
Pubmed ID:
28854168
human gut metagenome
(#408170)
Commensal bacteria make GPCR ligands that mimic human signalling molecules.,
Nature, 2017
Nature, 2017
Pubmed ID:
28854168
String Representations
InChiKey (Click to copy)
MZUNFYMZKTWADX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)20-18(16-21)17-22/h18,21-22H,2-17H2,1H3,(H,20,23)
SMILES (Click to copy)
CCCCCCCCCCCCCCCC(NC(CO)CO)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
17
Van der Waals Molecular Volume
371.99
Topological Polar Surface Area
69.56
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
4.79
Molar Refractivity
97.91
Admin
Created at
-
Updated at
19th Sep 2023