Showing Compound Eicosapentaenoic acid (FDB003102)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:39 UTC

Update date

2019-11-26 02:58:29 UTC

Primary ID

FDB003102

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Eicosapentaenoic acid

Description

Present in fish oils as an acylglycerol and in animal phospholipids. Nutriceutical with antioxidation props. Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). It also has the trivial name timnodonic acid. In chemical structure, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. It is obtained in the human diet by eating oily fish or fish oil— e.g., cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in human breast milk. [Wikipedia]. EPA is a biomarker for the consumption of salt-water fish.

CAS Number

10417-94-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Eicosapentaenoate	Generator
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoate	Generator
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid	biospider
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate	biospider
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid	biospider
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid	biospider
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoate	Generator
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid	biospider
(all-cis)-5,8,11,14,17-Eicosapentaenoic acid	biospider
(all-Z)-5,8,11,14,17-Eicosapentaenoate	Generator
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid	biospider
(all-Z)-Delta5,8,11,14,17-Eicosapentaenoic acid	biospider
(Z,Z,Z,Z,Z)-5,8,11,14,17-Eicosapentaenoic acid	biospider
5,8,11,14,17-EICOSAPENTAENOate	Generator
5,8,11,14,17-EICOSAPENTAENOIC ACID	ChEBI
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-	biospider
5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI)	biospider
5,8,11,14,17-Icosapentaenoate	Generator
5,8,11,14,17-Icosapentaenoic acid	ChEBI
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate	biospider
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid	biospider
all-cis-5,8,11,14,17-Eicosapentaenoate	Generator
all-cis-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoate	Generator
all-cis-Icosa-5,8,11,14,17-pentaenoic acid	biospider
all-cis-Icosapentaenoate	biospider
all-cis-Icosapentaenoic acid	biospider
C20:5 omega-3	biospider
cis-5,8,11,14,17-Eicosapentaenoate	biospider
cis-5,8,11,14,17-Eicosapentaenoic acid	biospider
cis-5,8,11,14,17-EPA	ChEBI
cis-delta(5,8,11,14,17)-Eicosapentaenoate	Generator
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid	biospider
cis-δ(5,8,11,14,17)-eicosapentaenoate	Generator
cis-δ(5,8,11,14,17)-eicosapentaenoic acid	Generator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoate	Generator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid	ChEBI
EPA	biospider
Icosapent	ChEBI
Icosapent, INN	db_source
Icosapentaenoate	biospider
Icosapentaenoic acid	biospider
Icosapento	ChEBI
Icosapentum	ChEBI
Timnodonate	biospider
Timnodonic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.00029 g/L	ALOGPS
logP	6.53	ALOGPS
logP	6.23	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	101.07 m³·mol⁻¹	ChemAxon
Polarizability	36.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H30O2

IUPAC name

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

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-IKHGVYGUSA-N

Isomeric SMILES

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

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 79.42%; H 10.00%; O 10.58%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28364

Phenol-Explorer ID

Not Available

DrugBank ID

DB00159

HMDB ID

HMDB01999

CRC / DFC (Dictionary of Food Compounds) ID

HDJ50-Z:CQZ50-L

EAFUS ID

Not Available

Dr. Duke ID

EICOSAPENTAENOIC-ACID

BIGG ID

2218016

KNApSAcK ID

C00000408

HET ID

EPA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Eicosapentaenoic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
5-hydroxyeicosatetraenoic-acid inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti atherotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti fibrosarcomic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti ischemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti leukotriene-B4	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti metastatic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti proliferant			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
collagenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
differentiator			DUKE
hypotensive			DUKE
nephroprotective	76595	Any protective agent that is able to prevent damage to the kidney.	DUKE
tyrosine-kinase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
VEGF inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Peroxisome proliferator-activated receptor delta	PPARD	Q03181