Details of the Drug

General Information of Drug (ID: DMCKH3P)

Drug Name
Anandamide
Synonyms
Anandamide; Arachidonylethanolamide; Arachidonoyl ethanolamide; N-Arachidonoylethanolamine; Anandamide (20.4, n-6); N-Arachidonoyl-2-hydroxyethylamide; 94421-68-8; AEA; N-arachidonoyl ethanolamine; N-(2-Hydroxyethyl)anachidonamide; 5,8,11,14-Eicosatetraenoylethanolamide; arachidonoylethanolamide; (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide; Arachidonoyl-EA; UNII-UR5G69TJKH; Arachidonic acid N-(hydroxyethyl)amide; Anandamide(20:4, n-6); Anandamide (20:4, n-6)
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) 347.5
Logarithm of the Partition Coefficient (xlogp) 5.4
Rotatable Bond Count (rotbonds) 16
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C22H37NO2
IUPAC Name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Canonical SMILES
CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)NCCO
InChI
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChIKey
LGEQQWMQCRIYKG-DOFZRALJSA-N
Cross-matching ID
PubChem CID
5281969
ChEBI ID
CHEMBL15848
CAS Number
94421-68-8
TTD ID
D0A9PS
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Regulation of Drug Effects [3]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [4]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [5]
Interstitial collagenase (MMP1) OTI4I2V1 MMP1_HUMAN Gene/Protein Processing [6]
Metalloproteinase inhibitor 1 (TIMP1) OTOXC51H TIMP1_HUMAN Gene/Protein Processing [6]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [7]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [8]
Stromelysin-1 (MMP3) OTGBI74Z MMP3_HUMAN Gene/Protein Processing [6]
Syncytin-1 (ERVW-1) OTWV8DXJ SYCY1_HUMAN Gene/Protein Processing [4]
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
Cannabinoid receptor 1 (CB1) DTT CNR1 5.59E-02 -0.22 -0.45
Cannabinoid receptor 1 (CB1) DTT CNR1 7.68E-01 -0.06 -0.46
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: 2364).
2 Opioid receptor and NO/cGMP pathway as a mechanism of peripheral antinociceptive action of the cannabinoid receptor agonist anandamide. Life Sci. 2009 Aug 26;85(9-10):351-6.
3 Intestinal P-glycoprotein exports endocannabinoids to prevent inflammation and maintain homeostasis. J Clin Invest. 2018 Aug 31;128(9):4044-4056. doi: 10.1172/JCI96817. Epub 2018 Aug 13.
4 Anandamide down-regulates placental transporter expression through CB2 receptor-mediated inhibition of cAMP synthesis. Pharmacol Res. 2019 Mar;141:331-342. doi: 10.1016/j.phrs.2019.01.002. Epub 2019 Jan 2.
5 Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury. Am J Physiol Lung Cell Mol Physiol. 2012 Jan 1;302(1):L111-9. doi: 10.1152/ajplung.00231.2011. Epub 2011 Sep 23.
6 R(+)-methanandamide and other cannabinoids induce the expression of cyclooxygenase-2 and matrix metalloproteinases in human nonpigmented ciliary epithelial cells. J Pharmacol Exp Ther. 2006 Mar;316(3):1219-28.
7 Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
8 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.