2-Arachidonylglycerol
General
Type : Acyl-Glycerol, Cannabinoid-Receptor-ligand, Natural
Chemical_Nomenclature : 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Canonical SMILES : CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO
InChI : InChI=1S\/C23H38O4\/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25\/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3\/b7-6-,10-9-,13-12-,16-15-
InChIKey : RCRCTBLIHCHWDZ-DOFZRALJSA-N
Other name(s) : 2-arachidonoylglycerol || Glyceryl 2-arachidonate || 2-Arachidonylglycerol || 2-AG || 2-Arachidonyl-glycerol || 2-Arachidonoyl-glycerol || 2-Arachidonoyl Glycerol || endocannabinoid 2-arachidonoylglycerol || 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol || 2-AG-D8 || 924894-97-3 || CHEMBL122972 || CHEBI:52392 || MG(0:0\/20:4(5Z,8Z,11Z,14Z)\/0:0) || 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol || SCHEMBL136277
MW : 378.55
Formula : C23H38O4
CAS_number : 53847-30-6
PubChem : 5282280
UniChem : RCRCTBLIHCHWDZ-DOFZRALJSA-N
Target
Structures : No structure
Families : Monoglyceridelipase_lysophospholip, ABHD6-Lip, Carb_B_Chordata, ABHD12-PHARC, abh_upf0017
References (19)
| Title : Carboxylesterase 1 mediates a distinctive metabolic profile of dendritic cells to attain an inflammatory phenotype - Elfiky_2024_J.Leukoc.Biol__ |
| Author(s) : Elfiky AMI , Lopez Cannizares J , Li J , Li Yim AYF , Verhoeven AJ , Ghiboub M , de Jonge WJ |
| Ref : J Leukoc Biol , : , 2024 |
| Abstract : |
| PubMedSearch : Elfiky_2024_J.Leukoc.Biol__ |
| PubMedID: 38869086 |
| Gene_locus related to this paper: human-CES1 |
| Title : Elevating levels of the endocannabinoid 2-arachidonoylglycerol blunts opioid reward but not analgesia - Martinez-Rivera_2024_bioRxiv__ |
| Author(s) : Martinez-Rivera A , Fetcho RN , Birmingham L , Jiu JX , Yang R , Foord C , Scala-Chavez D , Mekawy N , Pleil K , Pickel VM , Liston C , Castorena CM , Levitz J , Pan YX , Briand LA , Rajadhyaksha AM , Lee FS |
| Ref : Biorxiv , : , 2024 |
| Abstract : |
| PubMedSearch : Martinez-Rivera_2024_bioRxiv__ |
| PubMedID: 38766079 |
| Gene_locus related to this paper: human-MGLL |
| Title : 1-, 2- and 3-AG as substrates of the endocannabinoid enzymes and endogenous ligands of the cannabinoid receptor 1 - Farah_2021_Biochem.Biophys.Res.Commun_591_31 |
| Author(s) : Farah SI , Hilston S , Tran N , Zvonok N , Makriyannis A |
| Ref : Biochemical & Biophysical Research Communications , 591 :31 , 2021 |
| Abstract : |
| PubMedSearch : Farah_2021_Biochem.Biophys.Res.Commun_591_31 |
| PubMedID: 34995983 |
| Gene_locus related to this paper: human-ABHD6 , human-MGLL |
| Title : The endocannabinoid 2-arachidonoylglycerol inhibits endothelial function and repair - Jehle_2021_Int.J.Cardiol_323_243 |
| Author(s) : Jehle J , Eich L , Danisch M , Bagheri S , Avraamidou E , Pfeifer P , Tiyerili V , Bindila L , Lutz B , Nickenig G |
| Ref : Int J Cardiol , 323 :243 , 2021 |
| Abstract : |
| PubMedSearch : Jehle_2021_Int.J.Cardiol_323_243 |
| PubMedID: 32810540 |
| Title : Carboxylesterase 2 proteins are efficient diglyceride and monoglyceride lipases possibly implicated in metabolic disease - Chalhoub_2021_J.Lipid.Res__100075 |
| Author(s) : Chalhoub G , Kolleritsch S , Maresch LK , Taschler U , Pajed L , Tilp A , Natmessnig H , Rosina P , Kien B , Radner FPW , Schicho R , Oberer M , Schoiswohl G , Haemmerle G |
| Ref : J Lipid Res , :100075 , 2021 |
| Abstract : |
| PubMedSearch : Chalhoub_2021_J.Lipid.Res__100075 |
| PubMedID: 33872605 |
| Gene_locus related to this paper: human-CES2 , mouse-Ces2a , mouse-Ces2b , mouse-Ces2c |
| Title : The endocannabinoid 2-arachidonoylglycerol and dual ABHD6\/MAGL enzyme inhibitors display neuroprotective and anti-inflammatory actions in the in vivo retinal model of AMPA excitotoxicity - Kokona_2021_Neuropharmacol_185_108450 |
| Author(s) : Kokona D , Spyridakos D , Tzatzarakis M , Papadogkonaki S , Filidou E , Arvanitidis KI , Kolios G , Lamani M , Makriyannis A , Malamas MS , Thermos K |
| Ref : Neuropharmacology , 185 :108450 , 2021 |
| Abstract : |
| PubMedSearch : Kokona_2021_Neuropharmacol_185_108450 |
| PubMedID: 33450278 |
| Gene_locus related to this paper: human-ABHD6 , mouse-ABHD6 |
| Title : Inactivation of CES1 Blocks Prostaglandin D(2) Glyceryl Ester Catabolism in Monocytes\/Macrophages and Enhances Its Anti-inflammatory Effects, Whereas the Pro-inflammatory Effects of Prostaglandin E(2) Glyceryl Ester Are Attenuated - Scheaffer_2020_ACS.Omega_5_29177 |
| Author(s) : Scheaffer HL , Borazjani A , Szafran BN , Ross MK |
| Ref : ACS Omega , 5 :29177 , 2020 |
| Abstract : |
| PubMedSearch : Scheaffer_2020_ACS.Omega_5_29177 |
| PubMedID: 33225149 |
| Gene_locus related to this paper: human-CES1 |
| Title : Human leukocytes differentially express endocannabinoid-glycerol lipases and hydrolyze 2-arachidonoyl-glycerol and its metabolites from the 15-lipoxygenase and cyclooxygenase pathways - Turcotte_2019_J.Leukoc.Biol_106_1337 |
| Author(s) : Turcotte C , Dumais E , Archambault AS , Martin C , Blanchet MR , Bissonnette E , Boulet LP , Laviolette M , Di Marzo V , Flamand N |
| Ref : J Leukoc Biol , 106 :1337 , 2019 |
| Abstract : |
| PubMedSearch : Turcotte_2019_J.Leukoc.Biol_106_1337 |
| PubMedID: 31556464 |
| Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-ABHD16A , human-CES1 , human-LYPLA2 , human-PPT1 |
| Title : Pseudomonas aeruginosa esterase PA2949, a bacterial homolog of the human membrane esterase ABHD6: expression, purification and crystallization - Bleffert_2019_Acta.Crystallogr.F.Struct.Biol.Commun_75_270 |
| Author(s) : Bleffert F , Granzin J , Gohlke H , Batra-Safferling R , Jaeger KE , Kovacic F |
| Ref : Acta Crystallographica F Struct Biol Commun , 75 :270 , 2019 |
| Abstract : |
| PubMedSearch : Bleffert_2019_Acta.Crystallogr.F.Struct.Biol.Commun_75_270 |
| PubMedID: 30950828 |
| Gene_locus related to this paper: pseae-PA2949 |
| Title : Characterization of Endocannabinoid-Metabolizing Enzymes in Human Peripheral Blood Mononuclear Cells under Inflammatory Conditions - Szafran_2018_Molecules_23_ |
| Author(s) : Szafran BN , Lee JH , Borazjani A , Morrison P , Zimmerman G , Andrzejewski KL , Ross MK , Kaplan BLF |
| Ref : Molecules , 23 : , 2018 |
| Abstract : |
| PubMedSearch : Szafran_2018_Molecules_23_ |
| PubMedID: 30513753 |
| Title : Decreased anxiety in juvenile rats following exposure to low levels of chlorpyrifos during development - Carr_2017_Neurotoxicol_59_183 |
| Author(s) : Carr RL , Armstrong NH , Buchanan AT , Eells JB , Mohammed AN , Ross MK , Nail CA |
| Ref : Neurotoxicology , 59 :183 , 2017 |
| Abstract : |
| PubMedSearch : Carr_2017_Neurotoxicol_59_183 |
| PubMedID: 26642910 |
| Title : The Endocannabinoid Metabolite Prostaglandin E2 (PGE2)-Glycerol Inhibits Human Neutrophil Functions: Involvement of Its Hydrolysis into PGE2 and EP Receptors - Turcotte_2017_J.Immunol_198_3255 |
| Author(s) : Turcotte C , Zarini S , Jean S , Martin C , Murphy RC , Marsolais D , Laviolette M , Blanchet MR , Flamand N |
| Ref : J Immunol , 198 :3255 , 2017 |
| Abstract : |
| PubMedSearch : Turcotte_2017_J.Immunol_198_3255 |
| PubMedID: 28258202 |
| Title : Unconventional endocannabinoid signaling governs sperm activation via the sex hormone progesterone - Miller_2016_Science_352_555 |
| Author(s) : Miller MR , Mannowetz N , Iavarone AT , Safavi R , Gracheva EO , Smith JF , Hill RZ , Bautista DM , Kirichok Y , Lishko PV |
| Ref : Science , 352 :555 , 2016 |
| Abstract : |
| PubMedSearch : Miller_2016_Science_352_555 |
| PubMedID: 26989199 |
| Gene_locus related to this paper: human-ABHD2 |
| Title : Induction of endocannabinoid levels in juvenile rat brain following developmental chlorpyrifos exposure - Carr_2013_Toxicol.Sci_135_193 |
| Author(s) : Carr RL , Adams AL , Kepler DR , Ward AB , Ross MK |
| Ref : Toxicol Sci , 135 :193 , 2013 |
| Abstract : |
| PubMedSearch : Carr_2013_Toxicol.Sci_135_193 |
| PubMedID: 23761300 |
| Title : Inactivation of lipid glyceryl ester metabolism in human THP1 monocytes\/macrophages by activated organophosphorus insecticides: role of carboxylesterases 1 and 2 - Xie_2010_Chem.Res.Toxicol_23_1890 |
| Author(s) : Xie S , Borazjani A , Hatfield MJ , Edwards CC , Potter PM , Ross MK |
| Ref : Chemical Research in Toxicology , 23 :1890 , 2010 |
| Abstract : |
| PubMedSearch : Xie_2010_Chem.Res.Toxicol_23_1890 |
| PubMedID: 21049984 |
| Title : Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling - Hoover_2008_Bioorg.Med.Chem.Lett_18_5838 |
| Author(s) : Hoover HS , Blankman JL , Niessen S , Cravatt BF |
| Ref : Bioorganic & Medicinal Chemistry Lett , 18 :5838 , 2008 |
| Abstract : |
| PubMedSearch : Hoover_2008_Bioorg.Med.Chem.Lett_18_5838 |
| PubMedID: 18657971 |
| Title : Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol - Ho_2007_Br.J.Pharmacol_150_641 |
| Author(s) : Ho WS , Randall MD |
| Ref : British Journal of Pharmacology , 150 :641 , 2007 |
| Abstract : |
| PubMedSearch : Ho_2007_Br.J.Pharmacol_150_641 |
| PubMedID: 17245358 |
| Title : A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol - Blankman_2007_Chem.Biol_14_1347 |
| Author(s) : Blankman JL , Simon GM , Cravatt BF |
| Ref : Chemical Biology , 14 :1347 , 2007 |
| Abstract : |
| PubMedSearch : Blankman_2007_Chem.Biol_14_1347 |
| PubMedID: 18096503 |
| Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-MGLL |
| Title : Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol - Ghafouri_2004_Br.J.Pharmacol_143_774 |
| Author(s) : Ghafouri N , Tiger G , Razdan RK , Mahadevan A , Pertwee RG , Martin BR , Fowler CJ |
| Ref : British Journal of Pharmacology , 143 :774 , 2004 |
| Abstract : |
| PubMedSearch : Ghafouri_2004_Br.J.Pharmacol_143_774 |
| PubMedID: 15492019 |