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


Classification

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
Pubmed ID: 28854168
human gut metagenome (#408170)
Commensal bacteria make GPCR ligands that mimic human signalling molecules.,
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

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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

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Created at
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Updated at
19th Sep 2023