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179113-91-8

179113-91-8 | Glycine, N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]-

CAS No: 179113-91-8 Catalog No: AG0026SL MDL No:MFCD03791313

Product Description

Catalog Number:
AG0026SL
Chemical Name:
Glycine, N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]-
CAS Number:
179113-91-8
Molecular Formula:
C22H35NO3
Molecular Weight:
361.5182
MDL Number:
MFCD03791313
IUPAC Name:
2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]acetic acid
InChI:
InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-
InChI Key:
YLEARPUNMCCKMP-DOFZRALJSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O
NSC Number:
746569

Properties

Complexity:
476  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
4  
Exact Mass:
361.262g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
361.526g/mol
Monoisotopic Mass:
361.262g/mol
Rotatable Bond Count:
16  
Topological Polar Surface Area:
66.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.6  

Literature

Title Journal
Effects of cannabinoids and related fatty acids upon the viability of P19 embryonal carcinoma cells. Archives of toxicology 20131101
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands. Pharmacological reviews 20130701
Screening β-arrestin recruitment for the identification of natural ligands for orphan G-protein-coupled receptors. Journal of biomolecular screening 20130601
Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase. Bioorganic & medicinal chemistry 20120601
Reversible lysine acetylation regulates activity of human glycine N-acyltransferase-like 2 (hGLYATL2): implications for production of glycine-conjugated signaling molecules. The Journal of biological chemistry 20120511
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells. British journal of pharmacology 20120401
So what do we call GPR18 now? British journal of pharmacology 20120401
N-arachidonoyl glycine induces macrophage apoptosis via GPR18. Biochemical and biophysical research communications 20120210
N-Amino acid linoleoyl conjugates: anti-inflammatory activities. Bioorganic & medicinal chemistry letters 20120115
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
N-arachidonyl-glycine modulates synaptic transmission in superficial dorsal horn. British journal of pharmacology 20101001
N-arachidonoyl glycine, an endogenous lipid that acts as a vasorelaxant via nitric oxide and large conductance calcium-activated potassium channels. British journal of pharmacology 20100601
N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC neuroscience 20100101
Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport. The Journal of biological chemistry 20091225
T-type calcium channel inhibition underlies the analgesic effects of the endogenous lipoamino acids. The Journal of neuroscience : the official journal of the Society for Neuroscience 20091021
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nature chemical biology 20091001
N-arachidonylglycine causes ROS production and cytochrome c release in liver mitochondria. Free radical biology & medicine 20090901
Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation. The Journal of biological chemistry 20090619
Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay. The Journal of biological chemistry 20090501
Cannabinoids, endocannabinoids, and related analogs in inflammation. The AAPS journal 20090301
Inhibition of human recombinant T-type calcium channels by the endocannabinoid N-arachidonoyl dopamine. British journal of pharmacology 20090301
The endocannabinoid anandamide is a precursor for the signaling lipid N-arachidonoyl glycine by two distinct pathways. BMC biochemistry 20090101
Novel endogenous N-acyl glycines identification and characterization. Vitamins and hormones 20090101
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation. Bioorganic & medicinal chemistry 20081115
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine. Biochemical pharmacology 20081015
Identification of farnesyl pyrophosphate and N-arachidonylglycine as endogenous ligands for GPR92. The Journal of biological chemistry 20080725
Fatty acid amide hydrolase inhibition enhances the anti-allodynic actions of endocannabinoids in a model of acute pain adapted for the mouse. Neuroscience 20080717
Cytochrome c catalyzes the in vitro synthesis of arachidonoyl glycine. Biochemical and biophysical research communications 20080111
Actions of N-arachidonyl-glycine in a rat neuropathic pain model. Neuropharmacology 20080101
Potential anti-inflammatory actions of the elmiric (lipoamino) acids. Bioorganic & medicinal chemistry 20070515
Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Analytical biochemistry 20070115
Actions of N-arachidonyl-glycine in a rat inflammatory pain model. Molecular pain 20070101
N-Arachidonyl-glycine inhibits the glycine transporter, GLYT2a. Journal of neurochemistry 20061101
Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18. Biochemical and biophysical research communications 20060901
The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. Journal of medicinal chemistry 20050811
Identification of N-arachidonylglycine, U18666A, and 4-androstene-3,17-dione as novel insulin Secretagogues. Biochemical and biophysical research communications 20050805
Reduced endocannabinoid immune modulation by a common cannabinoid 2 (CB2) receptor gene polymorphism: possible risk for autoimmune disorders. Journal of leukocyte biology 20050701
Chemo-enzymatic synthesis of N-arachidonoyl glycine. Biotechnology letters 20040801
A structure-activity relationship study on N-arachidonoyl-amino acids as possible endogenous inhibitors of fatty acid amide hydrolase. Biochemical and biophysical research communications 20040130
Regulation of anandamide tissue levels by N-arachidonylglycine. Biochemical pharmacology 20021001
Selective oxygenation of N-arachidonylglycine by cyclooxygenase-2. Biochemical and biophysical research communications 20020823
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419

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