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
CHEBI:2700
CAS Number
94421-68-8
TTD ID
D0A9PS

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]
B1 bradykinin receptor (BDKRB1) OT1DHSVQ BKRB1_HUMAN Gene/Protein Processing [4]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [5]
Cannabinoid receptor 2 (CNR2) OTYP9P43 CNR2_HUMAN Gene/Protein Processing [6]
Cyclic AMP-responsive element-binding protein 1 (CREB1) OT1MDLA1 CREB1_HUMAN Post-Translational Modifications [5]
Cytochrome P450 2J2 (CYP2J2) OTJBTEH8 CP2J2_HUMAN Regulation of Drug Effects [7]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [8]
Glycoprotein hormones alpha chain (CGA) OT00U3Y3 GLHA_HUMAN Gene/Protein Processing [5]
Interstitial collagenase (MMP1) OTI4I2V1 MMP1_HUMAN Gene/Protein Processing [9]
Leptin (LEP) OT5Q7ODW LEP_HUMAN Regulation of Drug Effects [10]
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 The endocannabinoid anandamide inhibits kinin B1 receptor sensitization through cannabinoid CB1 receptor stimulation in human umbilical vein. Eur J Pharmacol. 2009 Jan 5;602(1):176-9. doi: 10.1016/j.ejphar.2008.10.058. Epub 2008 Nov 11.
5 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.
6 Localization and function of cannabinoid receptors in the corpus cavernosum: basis for modulation of nitric oxide synthase nerve activity. Eur Urol. 2010 Feb;57(2):342-8. doi: 10.1016/j.eururo.2008.12.024. Epub 2009 Jan 3.
7 Cross-talk of cannabinoid and endocannabinoid metabolism is mediated via human cardiac CYP2J2. J Inorg Biochem. 2018 Jul;184:88-99. doi: 10.1016/j.jinorgbio.2018.03.016. Epub 2018 Apr 7.
8 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.
9 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.
10 Further insights into the regulation of human FAAH by progesterone and leptin implications for endogenous levels of anandamide and apoptosis of immune and neuronal cells. Neurotoxicology. 2005 Oct;26(5):811-7.