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
CHEBI:52392
CAS Number
53847-30-6
TTD ID
D06JBN

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]
Cannabinoid receptor 2 (CNR2) OTYP9P43 CNR2_HUMAN Drug Response [5]
Cocaine esterase (CES2) OTC647SQ EST2_HUMAN Biotransformations [6]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [7]
Cyclic AMP-responsive element-binding protein 3-like protein 3 (CREB3L3) OTDMU3GP CR3L3_HUMAN Gene/Protein Processing [3]
Cytochrome P450 7A1 (CYP7A1) OT8Z5KLD CP7A1_HUMAN Gene/Protein Processing [3]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [7]
Endoplasmic reticulum chaperone BiP (HSPA5) OTFUIRAO BIP_HUMAN Gene/Protein Processing [7]
Estrogen-related receptor gamma (ESRRG) OTC3A0KU ERR3_HUMAN Regulation of Drug Effects [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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 Functional consequences of nonsynonymous single nucleotide polymorphisms in the CB2 cannabinoid receptor. Pharmacogenet Genomics. 2010 Mar;20(3):157-66. doi: 10.1097/FPC.0b013e3283367c6b.
6 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.
7 The endocannabinoid 2-arachidonoylglycerol promotes endoplasmic reticulum stress in placental cells. Reproduction. 2020 Aug;160(2):171-180. doi: 10.1530/REP-19-0539.
8 An inverse agonist of estrogen-related receptor regulates 2-arachidonoylglycerol synthesis by modulating diacylglycerol lipase expression in alcohol-intoxicated mice. Arch Toxicol. 2020 Feb;94(2):427-438. doi: 10.1007/s00204-019-02648-7. Epub 2020 Jan 7.