Details of the Drug

General Information of Drug (ID: DMF1CM7)

Drug Name
Icosapentum
Synonyms
Eicosapentaenoic acid; Icosapent; Icosapent [INN]; Icosapentaenoic acid; Icosapento; Cis-5,8,11,14,17-eicosapentaenoic acid; Timnodonic acid; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic acid; 10417-94-4; 5,8,11,14,17-EICOSAPENTAENOIC ACID; 5,8,11,14,17-Icosapentaenoic acid; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid; AAN7QOV9EA; C20:5 omega-3; CCRIS 3279; CHEBI:28364; CHEMBL460026; EPA; UNII-AAN7QOV9EA; cis-5,8,11,14,17-Eicosapentaenoic acid
Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 302.5
Logarithm of the Partition Coefficient (xlogp) 5.6
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C20H30O2
IUPAC Name
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Canonical SMILES
CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
InChI
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey
JAZBEHYOTPTENJ-JLNKQSITSA-N
Cross-matching ID
PubChem CID
446284
ChEBI ID
CHEMBL460026
CAS Number
10417-94-4
UNII
AAN7QOV9EA
DrugBank ID
DB00159
INTEDE ID
DR1991
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP 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-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) DE492CE PGH2_HUMAN Substrate [1]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [2]
Cytochrome b-245 light chain (CYBA) OT16N9ZO CY24A_HUMAN Gene/Protein Processing [3]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [4]
Glutathione S-transferase Mu 2 (GSTM2) OTG4WT05 GSTM2_HUMAN Gene/Protein Processing [5]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [6]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Gene/Protein Processing [7]
Resistin (RETN) OTW5Z1NH RETN_HUMAN Gene/Protein Processing [8]
Stromelysin-2 (MMP10) OTJDWW8Q MMP10_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Divergent cyclooxygenase responses to fatty acid structure and peroxide level in fish and mammalian prostaglandin H synthases. FASEB J. 2006 Jun;20(8):1097-108.
2 Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal. Chem Biol Interact. 2014 Dec 5;224:42-50. doi: 10.1016/j.cbi.2014.10.008. Epub 2014 Oct 17.
3 The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. Metabolism. 2001 Jan;50(1):3-11.
4 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
5 Astaxanthin and omega-3 fatty acids individually and in combination protect against oxidative stress via the Nrf2-ARE pathway. Food Chem Toxicol. 2013 Dec;62:869-75.
6 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.
7 Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. Atherosclerosis. 2007 Mar;191(1):11-21. doi: 10.1016/j.atherosclerosis.2006.04.018. Epub 2006 May 30.
8 Fatty acids and expression of adipokines. Biochim Biophys Acta. 2005 May 30;1740(2):287-92. doi: 10.1016/j.bbadis.2004.11.019. Epub 2004 Dec 8.
9 Eicosapentaenoic acid and docosahexaenoic acid inhibit macrophage-induced gastric cancer cell migration by attenuating the expression of matrix metalloproteinase 10. J Nutr Biochem. 2012 Nov;23(11):1434-9. doi: 10.1016/j.jnutbio.2011.09.004. Epub 2012 Jan 27.