EPA

5,8,11,14,17-EICOSAPENTAENOIC ACID

Created:	1999-07-08
Last modified:	2011-06-04

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8 entries where EPA is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	52
Chiral Atom Count	0
Bond Count	51
Aromatic Bond Count	0

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Chemical Component Summary
Name	5,8,11,14,17-EICOSAPENTAENOIC ACID
Systematic Name (OpenEye OEToolkits)	(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Formula	C₂₀ H₃₀ O₂
Molecular Weight	302.451
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
SMILES	CACTVS	3.341	CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O
SMILES	OpenEye OEToolkits	1.5.0	CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Canonical SMILES	CACTVS	3.341	CC\C=C/C/C=C\C\C=C/C/C=C\C\C=C/CCCC(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O
InChI	InChI	1.03	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	InChI	1.03	JAZBEHYOTPTENJ-JLNKQSITSA-N

Drug Info: DrugBank

DrugBank ID	DB00159
Name	Icosapent
Groups	approved nutraceutical
Description	Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.
Synonyms	all-cis-icosa-5,8,11,14,17-pentaenoic acid (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid cis-5,8,11,14,17-eicosapentaenoic acid all-cis-5,8,11,14,17-eicosapentaenoic acid (all-Z)-5,8,11,14,17-eicosapentaenoic acid (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid 5,8,11,14,17-eicosapentaenoic acid cis-delta(5,8,11,14,17)-Eicosapentaenoic acid Eicosapentaenoic acid Timnodonic acid EPA Icosapent sodium all-cis-5,8,11,14,17-icosapentaenoic acid Icosapento Icosapentum (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate Icosapent Icosapentaenoic acid (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid 5,8,11,14,17-Icosapentaenoic acid cis-5,8,11,14,17-EPA
Brand Names	Herbalifeline Se-Plete DHA Tricare Prenatal DHA One Docosavit Folcaps Omega-3 Tricare Prenatal DHA One With Folate Virt-Care One Vp-pnv-dha Natelle One CitraNatal Assure Super Omega 3 Vp-CH-pnv natelle COMPLETE Tricare Prenatal 2-part Daily Prenatal Vitamin System Prenate Essential Virt-Bal DHA Plus Cavan One Zatean-Pn Plus Virt-PN Plus A2A Omega-3 Protect Cardio AF Oveeza Premium Omega 3 Tricare Prenatal Twist-off DHA Soft Quick Dissolve BP Vit 3 Ultra Omega 3 Nutri-Tab OB plus DHA Melittin Joint Soothing Ge Se-Tan DHA Pre-Tabs DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Dothelle DHA Tricare Prenatal DHA One Rx Multivitamin Taliva NESTABS DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA WesCap-C-DHA Animi-3 with Vitamin D CitraNatal Essence UltimateCare ONE NF Reliven VITAFOL Gummies PNV-Omega Virt-C DHA Folcaps Care One TL-Care DHA Taliment WestGel DHA Gesticare DHA NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA A2A Omega 3 Animi-3 CitraNatal DHA TriStart DHA Omega-3 Iq Childrens Chewable Gel
Indication	EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
Categories	Agents causing hyperkalemia Agents that produce hypertension Anti-Inflammatory Agents Anti-Inflammatory Agents, Non-Steroidal Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) Dietary Fats Dietary Fats, Unsaturated Dietary Supplements Eicosanoids Fats Fatty Acids Fatty Acids, Omega-3 Fatty Acids, Unsaturated Fish Oils Hypolipidemic Agents Lipids Nephrotoxic agents Non COX-2 selective NSAIDS Oils Supplements
CAS number	10417-94-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Prostaglandin G/H synthase 2	MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...	unknown	inhibitor
Prostaglandin G/H synthase 1	MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...	unknown	inhibitor
Peroxisome proliferator-activated receptor gamma	MGETLGDSPIDPESDSFTDTLSANISQEMTMVDTEMPFWPTNFGISSVDL...	unknown	agonist,regulator
Peroxisome proliferator-activated receptor delta	MEQPQEEAPEVREEEEKEEVAEAEGAPELNGGPQHALPSSSYTDLSRSSS...	unknown	agonist
Free fatty acid receptor 1	MDLPPQLSFGLYVAAFALGFPLNVLAIRGATAHARLRLTPSLVYALNLGC...	unknown	agonist
Sodium/calcium exchanger 1	MYNMRRLSLSPTFSMGFHLLVTVSLLFSHVDHVIAETEMEGEGNETGECT...	unknown	inhibitor
Fatty acid-binding protein, brain	MVEAFCATWKLTNSQNFDEYMKALGVGFATRQVGNVTKPTVIISQEGDKV...	unknown	agonist
Fatty acid desaturase 1	MAPDPVAAETAAQGPTPRYFTWDEVAQRSGCEERWLVIDRKVYNISEFTR...	unknown	agonist
Long-chain-fatty-acid--CoA ligase 4	MKLKLNVLTIILLPVHLLITIYSALIFIPWYFLTNAKKKNAMAKRIKAKP...	unknown	inducer
Transient receptor potential cation channel subfamily V member 1	MKKWSSTDLGAAADPLQKDTCPDPLDGDPNSRPPPAKPQLSTAKSRTRLF...	unknown	inducer
Peroxisome proliferator-activated receptor alpha	MVDTESPLCPLSPLEAGDLESPLSEEFLQEMGNIQEISQSIGEDSSGSFG...	unknown
Arachidonate 5-lipoxygenase	MPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682