Details of the Drug

General Information of Drug (ID: DMM0KOJ)

Drug Name
2-arachidonoylglycerol
Synonyms
2-arachidonoylglycerol; 2-AG; 2-Arachidonylglycerol; 2-Arachidonyl-glycerol; 53847-30-6; 2-Arachidonoyl-glycerol; 2-Arachidonoyl Glycerol; 2-Ara-Gl; 2-Monoarachidonoylglycerol; UNII-8D239QDW64; 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate; CHEMBL122972; CHEBI:52392; RCRCTBLIHCHWDZ-DOFZRALJSA-N; 8D239QDW64; MG(20:4); MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0); 5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,8Z,11Z,14Z)-; 5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethy
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 378.5
Logarithm of the Partition Coefficient (xlogp) 5.3
Rotatable Bond Count (rotbonds) 18
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C23H38O4
IUPAC Name
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Canonical SMILES
CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=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
Cross-matching ID
PubChem CID
5282280
ChEBI ID
CHEMBL122972
CAS Number
53847-30-6
TTD ID
D06JBN
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fatty acid amide hydrolase (FAAH) TTDP1UC NOUNIPROTAC Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase (CYP8B1) OTRI4UR1 CP8B1_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [4]
Cocaine esterase (CES2) OTC647SQ EST2_HUMAN Biotransformations [5]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [6]
Cyclic AMP-responsive element-binding protein 3-like protein 3 (CREB3L3) OTDMU3GP CR3L3_HUMAN Gene/Protein Processing [3]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [6]
Eukaryotic translation initiation factor 2 subunit 1 (EIF2S1) OTM0GDTP IF2A_HUMAN Post-Translational Modifications [6]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [4]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [7]
Sterol 26-hydroxylase, mitochondrial (CYP27A1) OT649C01 CP27A_HUMAN Gene/Protein Processing [3]
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Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Fatty acid amide hydrolase (FAAH) DTT NO-GeName 2.65E-01 0.02 0.1
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 729).
2 Conformationally constrained analogues of 2-arachidonoylglycerol. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5959-63.
3 Hepatic cannabinoid receptor type 1 mediates alcohol-induced regulation of bile acid enzyme genes expression via CREBH. PLoS One. 2013 Jul 22;8(7):e68845.
4 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells. J Biochem. 2004 Apr;135(4):517-24. doi: 10.1093/jb/mvh063.
5 Inactivation of lipid glyceryl ester metabolism in human THP1 monocytes/macrophages by activated organophosphorus insecticides: role of carboxylesterases 1 and 2. Chem Res Toxicol. 2010 Dec 20;23(12):1890-904. doi: 10.1021/tx1002194.
6 The endocannabinoid 2-arachidonoylglycerol promotes endoplasmic reticulum stress in placental cells. Reproduction. 2020 Aug;160(2):171-180. doi: 10.1530/REP-19-0539.
7 Cannabinoid-induced cell death in endometrial cancer cells: involvement of TRPV1 receptors in apoptosis. J Physiol Biochem. 2018 May;74(2):261-272. doi: 10.1007/s13105-018-0611-7. Epub 2018 Feb 13.