ChemFOnt: Showing chemical card for (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate (CFc000337433)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:31:11 UTC

Chemfont ID

CFc000337433

Molecule Identification

Common Name

(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate

Definition

Icosapent, also known as icosapentaenoate or (5z,8z,11z,14z,17z)-eicosapentaenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, icosapent is considered to be a fatty acid lipid molecule. Icosapent is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Icosapent can be found in a number of food items such as barley, sacred lotus, white lupine, and rape, which makes icosapent a potential biomarker for the consumption of these food products. Icosapent can be found primarily in blood, feces, sweat, and urine, as well as throughout most human tissues. In humans, icosapent is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, icosapent is found to be associated with essential hypertension and hypertension. Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl) is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials . The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40 (DrugBank).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid	ChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACID	ChEBI
5,8,11,14,17-Icosapentaenoic acid	ChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acid	ChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid	ChEBI
cis-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
cis-5,8,11,14,17-EPA	ChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid	ChEBI
EPA	ChEBI
Icosapent	ChEBI
Icosapentaenoic acid	ChEBI
Icosapento	ChEBI
Icosapentum	ChEBI
Timnodonic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoate	Kegg
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid	Kegg
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid	Kegg
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoate	Generator
(all-Z)-5,8,11,14,17-Eicosapentaenoate	Generator
5,8,11,14,17-EICOSAPENTAENOate	Generator
5,8,11,14,17-Icosapentaenoate	Generator
all-cis-5,8,11,14,17-Eicosapentaenoate	Generator
all-cis-Icosa-5,8,11,14,17-pentaenoate	Generator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoate	Generator
cis-5,8,11,14,17-Eicosapentaenoate	Generator
cis-delta(5,8,11,14,17)-Eicosapentaenoate	Generator
cis-Δ(5,8,11,14,17)-eicosapentaenoate	Generator
cis-Δ(5,8,11,14,17)-eicosapentaenoic acid	Generator
Icosapentaenoate	Generator
Timnodonate	Generator
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate	Generator
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoate	Generator
Eicosapentaenoate	Generator
Omega-3-eicosapentaenoic acid	HMDB
Acid, eicosapentanoic	HMDB
Eicosapentanoic acid	HMDB
Omega 3 eicosapentaenoic acid	HMDB
all-cis-Icosapentaenoate	HMDB
all-cis-Icosapentaenoic acid	HMDB
(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acid	HMDB
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid	HMDB
(all-Z)-Δ5,8,11,14,17-eicosapentaenoic acid	HMDB
(all-cis)-5,8,11,14,17-Eicosapentaenoic acid	HMDB
FA(20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
FA(20:5n3)	HMDB
Eicosapentaenoic acid	HMDB

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

Traditional Name

eicosapentaenoic acid

CAS Registry Number

10417-94-4

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

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-

InChI Key

JAZBEHYOTPTENJ-JLNKQSITSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Showing chemical card for (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate (CFc000337433)

MOL for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

3D MOL for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

3D SDF for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

3D-SDF for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

PDB for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

3D PDB for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

SMILES for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

INCHI for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

Structure for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

3D Structure for CFc000337433 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)