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870819P

Avanti

N-oleoylglycine

powder

Empirical Formula (Hill Notation):
C20H37NO3
CAS Number:
Molecular Weight:
339.51

form

powder

packaging

pkg of 1 × 10 mg (870819P-10mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCC/C=C\CCCCCCCC(NCC(O)=O)=O

InChI

1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

InChI key

HPFXACZRFJDURI-KTKRTIGZSA-N

General description

N-oleoylglycine is an endogenous lipid containing glycine moiety in the head group. N-oleoylglycine structure contains an oleic acid, which is amide linked to glycine.

Application

N-oleoylglycine has been used as a related endogenous compound to investigate the nature of the lipid head group required for OLCarn activity at GlyT2 (glycine transporter 2).

Biochem/physiol Actions

N-oleoylglycine acts as a substrate for peptidylglycine α amidating monooxygenase (PAM) for synthesis of oleoylamide. It is also involved in activation of G?protein?coupled receptor GPR132.

Packaging

5 mL Amber Glass Screw Cap Vial (870819P-10mg)

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Shalini Chaturvedi et al.
Prostaglandins & other lipid mediators, 81(3-4), 136-149 (2006-11-07)
Oleamide (cis-9-octadecenamide) is a member of an emerging class of lipid-signaling molecules, the primary fatty acid amides. A growing body of evidence indicates that oleamide mediates fundamental neurochemical processes including sleep, thermoregulation, and nociception. Nevertheless, the mechanism for oleamide biosynthesis...
J E Carland et al.
British journal of pharmacology, 168(4), 891-902 (2012-09-18)
Concentrations of extracellular glycine in the CNS are regulated by two Na(+)/Cl(-) -dependent glycine transporters, GlyT1 and GlyT2. Selective inhibitors of GlyT1 have been developed for the treatment of schizophrenia, whilst selective inhibitors of GlyT2 are analgesic in animal models...
Heather B Bradshaw et al.
Vitamins and hormones, 81, 191-205 (2009-08-04)
Discovery of the endogenous cannabinoid and N-acyl amide, anandamide (N-arachidonoyl ethanolamine), paved the way for lipidomics discoveries in the growing family of N-acyl amides. Lipidomics is a field that is broadening our view of the molecular world to include a...
D J Merkler et al.
Archives of biochemistry and biophysics, 330(2), 430-434 (1996-06-15)
Fatty acid primary amides have recently been recognized as mammalian hormones [Cravatt et al. (1995) Science 268, 1506-1509]. The route to their biosynthesis is unknown. Many mammalian peptide hormones also possess a C-terminal alpha-amide moiety that arises from the posttranslational...
James R Foster et al.
Pharmacology research & perspectives, 7(6), e00542-e00542 (2019-11-27)
The G-protein-coupled receptor GPR132, also known as G2A, is activated by 9-hydroxyoctadecadienoic acid (9-HODE) and other oxidized fatty acids. Other suggested GPR132 agonists including lysophosphatidylcholine (LPC) have not been readily reproduced. Here, we identify N-acylamides in particular N-acylglycines, as lipid...

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