Structure Database (LMSD)

Common Name
Oleoyl Serinol
Systematic Name
N-(1,3-dihydroxypropan-2-yl)9Z-octadecenamide
Synonyms
LM ID
LMFA08020463
Formula
Exact Mass
Calculate m/z
355.308644
Sum Composition
Status
Curated

Classification

Biological Context

Oleoyl serinol is a gut microbe-derived agonist of GPR119.1 It stimulates secretion of GLP-1 in vitro (IC50 = 12 µM).2 Oleoyl serinol has a variety of meal-related effects in mice, including a reduction of plasma insulin, but not leptin, levels in ad libitum-fed mice and an increase in both plasma insulin and leptin levels in mice fasted for 12 hours, then refed.1 It alters the circadian oscillations of mouse plasma phosphatidylcholine and ceramide levels in a molecular species-specific manner. Oleoyl serinol (100 µM) also reduces cell viability of F-11 neuroblastoma cells and induces apoptosis in U87 astrocytoma cells.3 At 80 µM, it induces formation of a complex including PAR-4 and PKCζ in embryoid body-derived cells, decreases the levels of the pluripotency marker Oct-4 and prostate apoptosis response-4 (PAR-4), which mediates ceramide-induced apoptosis in embryonic stem cells.4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
human gut metagenome (#408170)
Commensal bacteria make GPCR ligands that mimic human signalling molecules.,
Nature, 2017
Pubmed ID: 28854168
Escherichia coli (#562)
Gammaproteobacteria (#1236)
Commensal bacteria make GPCR ligands that mimic human signalling molecules.,
Nature, 2017
Pubmed ID: 28854168

String Representations

InChiKey (Click to copy)
LGDVTFHRZXBSJM-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C21H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)22-20(18-23)19-24/h9-10,20,23-24H,2-8,11-19H2,1H3,(H,22,25)/b10-9-
SMILES (Click to copy)
N(C(CCCCCCC/C=C\CCCCCCCC)=O)C(CO)CO

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings
Aromatic Rings
Rotatable Bonds 18
Van der Waals Molecular Volume 403.95
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 5.35
Molar Refractivity 107.05

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Created at
26th Jun 2026
Updated at
26th Jun 2026