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
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
JAZBEHYOTPTENJ-JLNKQSITSA-N
InChIKey
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-
Cross-matching ID
PubChem CID
446284
ChEBI ID
CHEBI:28364
CAS Number
10417-94-4
DrugBank ID
DB00159
INTEDE ID
DR1991

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
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Protein Interaction/Cellular Processes [2]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [3]
ATP-binding cassette sub-family G member 1 (ABCG1) OT5BG6MK ABCG1_HUMAN Gene/Protein Processing [4]
Cytochrome b-245 light chain (CYBA) OT16N9ZO CY24A_HUMAN Gene/Protein Processing [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [6]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [6]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [6]
Cytochrome P450 2E1 (CYP2E1) OTHQ17JG CP2E1_HUMAN Gene/Protein Processing [6]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [6]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [7]
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 Eicosapentaenoic acid and rosiglitazone increase adiponectin in an additive and PPAR-dependent manner in human adipocytes. Obesity (Silver Spring). 2011 Feb;19(2):262-8. doi: 10.1038/oby.2010.186. Epub 2010 Sep 2.
3 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.
4 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.
5 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.
6 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
7 Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. Br J Nutr. 2006 Nov;96(5):811-9.