2-Arachidonylglycerol
True natural ligand for cannabinoid type-1 (CB1) receptors and the most abundant endogenous cannabinoid. 2-AG binds to the cannabinoid receptors (CB1 and CB2) and exhibits a variety of cannabimimetic activities in vitro and in vivo originally identified as the targets of Delta9-tetrahydocannabinol (-)-Delta9-tetrahydrocannabinol (THC), the psychoactive component of cannabis. Fatty acid amide hydrolase (FAAH) is the main AEA hydrolase, whereas a monoacylglycerol lipase (MAGL) is critical in degrading 2-AG. Monoacylglycerol lipase ABHD2 is a steroid-activating enzyme that hydrolyzes 2-arachidonoylglycerol. ABHD2 is expressed in sperm and in ovaries. MGLL terminates action of 2-AG, FAAH (fatty acid acyl hydrolase not an A/B hydrolase) terminates action of Anandamide both substrates are natural ligand of cannabinoid receptors and both give arachidonic acid
General
Type : Acyl-Glycerol, Cannabinoid-Receptor-ligand, Natural, Arachidonate
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 (21)
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| Gene_locus related to this paper: human-CES1 |
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| 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__ |
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| Gene_locus related to this paper: human-MGLL |
| 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 |
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| Gene_locus related to this paper: human-ABHD6 , mouse-ABHD6 |
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| Gene_locus related to this paper: human-ABHD6 , human-MGLL |
| Title : Carboxylesterase 2 proteins are efficient diglyceride and monoglyceride lipases possibly implicated in metabolic disease - Chalhoub_2021_J.Lipid.Res__100075 |
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| Gene_locus related to this paper: human-CES2 , mouse-Ces2a , mouse-Ces2b , mouse-Ces2c |
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| Gene_locus related to this paper: pig-PLE1 , pig-a0a1s6l967 |
| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| Abstract : |
| PubMedSearch : Blankman_2007_Chem.Biol_14_1347 |
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| Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-MGLL |
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| Abstract : |
| PubMedSearch : Ho_2007_Br.J.Pharmacol_150_641 |
| PubMedID: 17245358 |
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| PubMedSearch : Ghafouri_2004_Br.J.Pharmacol_143_774 |
| PubMedID: 15492019 |