NP-MRD: Showing NP-Card for Ethyl icosapentate (NP0338200)

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Record Information

Version

2.0

Created at

2024-09-11 14:18:24 UTC

Updated at

2024-09-11 14:18:24 UTC

NP-MRD ID

NP0338200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl icosapentate

Description

Ethyl icosapentate, also known as icosapent or epadel, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl icosapentate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Studies suggest that EPA reduces hepatic very low-density lipoprotein triglycerides (VLDL-TG) synthesis and/or secretion and enhances TG clearance from circulating VLDL particles. Ethyl icosapentate or Ethyl icosapentate is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). Outside of the human body, Ethyl icosapentate has been detected, but not quantified in, fishes. This could make ethyl icosapentate a potential biomarker for the consumption of these foods. Potential mechanisms of action include increased β-oxidation; inhibition of acyl-CoA:1,2-Diacylglycerol acyltransferase (DGAT); decreased lipogenesis in the liver; and increased plasma lipoprotein lipase activity. It is used as adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL). Once converted into active EPA, it is hepatically metabolized into acetyl Coenzyme A via beta-oxidation. Ethyl icosapentate was first documented in 2012 (PMID: 22819432). FDA approved on July 26, 2012 (PMID: 22894624) (PMID: 23312052) (PMID: 23325450) (PMID: 23701295) (PMID: 23835245) (PMID: 23992935).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061311122D          

 24 23  0  0  0  0            999 V2000
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24  4  1  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-

> <INCHI_KEY>
SSQPWTVBQMWLSZ-AAQCHOMXSA-N

> <FORMULA>
C22H34O2

> <MOLECULAR_WEIGHT>
330.5042

> <EXACT_MASS>
330.255880332

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
40.32301674292739

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
6.727951165

> <ALOGPS_LOGS>
-6.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.03224093634593

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
110.5883

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.83e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl eicosapentaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   24                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24    4   22                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoic acid ethyl ester	ChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl ester	ChEBI
all-cis-Ethyl 5,8,11,14,17-icosapentaenoate	ChEBI
AMR 101	ChEBI
AMR101	ChEBI
cis-Eicosapentaenoic acid ethyl ester	ChEBI
e-EPA	ChEBI
Eicosapentaenoic acid ethyl ester	ChEBI
Epadel	ChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate	ChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate	ChEBI
Ethyl (all cis)-5,8,11,14,17-icosapentaenoate	ChEBI
Ethyl all-cis-5,8,11,14,17-icosapentaenoate	ChEBI
Ethyl eicosapentaenoate	ChEBI
Icosapent	ChEBI
Icosapent ethyl	ChEBI
Timnodonic acid ethyl ester	ChEBI
Vascepa	ChEBI
EPA ethyl ester	Kegg
Epadel S	Kegg
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoate ethyl ester	Generator
(all-Z)-5,8,11,14,17-Eicosapentaenoate ethyl ester	Generator
all-cis-Ethyl 5,8,11,14,17-icosapentaenoic acid	Generator
cis-Eicosapentaenoate ethyl ester	Generator
Eicosapentaenoate ethyl ester	Generator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid	Generator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid	Generator
Ethyl (all cis)-5,8,11,14,17-icosapentaenoic acid	Generator
Ethyl all-cis-5,8,11,14,17-icosapentaenoic acid	Generator
Ethyl eicosapentaenoic acid	Generator
Timnodonate ethyl ester	Generator
Ethyl icosapentic acid	Generator
Eicosapentaenoic acid, ethyl ester	HMDB
Epa-e	HMDB
Ethyl epa	HMDB
Ethyl ester(all-Z)-5,8,11,14,17-eicosapentaenoic acid	HMDB
Ethyl icosapentaenoate	HMDB
Ethyl icosapentate, jan	HMDB
MND 21	HMDB
AMR-101	MeSH
Ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate	MeSH
Ethyl icosapentate	ChEBI

Chemical Formula

C₂₂H₃₄O₂

Average Mass

330.5042 Da

Monoisotopic Mass

330.25588 Da

IUPAC Name

ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Traditional Name

ethyl eicosapentaenoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-

InChI Key

SSQPWTVBQMWLSZ-AAQCHOMXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid ethyl ester (CHEBI:84883 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.8	ALOGPS
logP	6.73	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	110.59 m³·mol⁻¹	ChemAxon
Polarizability	40.32 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

External Links

HMDB ID

HMDB0039530

DrugBank ID

DB08887

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019145

KNApSAcK ID

Not Available

Chemspider ID

8007147

KEGG Compound ID

C16184

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl_eicosapentaenoic_acid

METLIN ID

Not Available

PubChem Compound

9831415

PDB ID

Not Available

ChEBI ID

84883

Good Scents ID

Not Available

References

General References

Ballantyne CM, Bays HE, Kastelein JJ, Stein E, Isaacsohn JL, Braeckman RA, Soni PN: Efficacy and safety of eicosapentaenoic acid ethyl ester (AMR101) therapy in statin-treated patients with persistent high triglycerides (from the ANCHOR study). Am J Cardiol. 2012 Oct 1;110(7):984-92. doi: 10.1016/j.amjcard.2012.05.031. Epub 2012 Jul 20. [PubMed:22819432 ]
Jacobson TA: A new pure omega-3 eicosapentaenoic acid ethyl ester (AMR101) for the management of hypertriglyceridemia: the MARINE trial. Expert Rev Cardiovasc Ther. 2012 Jun;10(6):687-95. doi: 10.1586/erc.12.56. [PubMed:22894624 ]
Bays HE, Braeckman RA, Ballantyne CM, Kastelein JJ, Otvos JD, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on lipoprotein particle concentration and size in patients with very high triglyceride levels (the MARINE study). J Clin Lipidol. 2012 Nov-Dec;6(6):565-72. doi: 10.1016/j.jacl.2012.07.001. Epub 2012 Jul 24. [PubMed:23312052 ]
Bays HE, Ballantyne CM, Braeckman RA, Stirtan WG, Soni PN: Icosapent ethyl, a pure ethyl ester of eicosapentaenoic acid: effects on circulating markers of inflammation from the MARINE and ANCHOR studies. Am J Cardiovasc Drugs. 2013 Feb;13(1):37-46. doi: 10.1007/s40256-012-0002-3. [PubMed:23325450 ]
Ballantyne CM, Braeckman RA, Soni PN: Icosapent ethyl for the treatment of hypertriglyceridemia. Expert Opin Pharmacother. 2013 Jul;14(10):1409-16. doi: 10.1517/14656566.2013.798645. Epub 2013 May 24. [PubMed:23701295 ]
Brinton EA, Ballantyne CM, Bays HE, Kastelein JJ, Braeckman RA, Soni PN: Effects of icosapent ethyl on lipid and inflammatory parameters in patients with diabetes mellitus-2, residual elevated triglycerides (200-500 mg/dL), and on statin therapy at LDL-C goal: the ANCHOR study. Cardiovasc Diabetol. 2013 Jul 9;12:100. doi: 10.1186/1475-2840-12-100. [PubMed:23835245 ]
Braeckman RA, Manku MS, Bays HE, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on plasma and red blood cell fatty acids in patients with very high triglyceride levels (results from the MARINE study). Prostaglandins Leukot Essent Fatty Acids. 2013 Sep;89(4):195-201. doi: 10.1016/j.plefa.2013.07.005. Epub 2013 Aug 1. [PubMed:23992935 ]
Weintraub H: Update on marine omega-3 fatty acids: management of dyslipidemia and current omega-3 treatment options. Atherosclerosis. 2013 Oct;230(2):381-9. doi: 10.1016/j.atherosclerosis.2013.07.041. Epub 2013 Jul 31. [PubMed:24075771 ]
Nelson SD, Munger MA: Icosapent ethyl for treatment of elevated triglyceride levels. Ann Pharmacother. 2013 Nov;47(11):1517-23. doi: 10.1177/1060028013504079. Epub 2013 Nov 5. [PubMed:24259598 ]
Hilleman DE, Malesker MA: Potential benefits of icosapent ethyl on the lipid profile: case studies. Clin Med Insights Cardiol. 2014 Feb 2;8:13-5. doi: 10.4137/CMC.S13571. eCollection 2014. [PubMed:24516343 ]

Showing NP-Card for Ethyl icosapentate (NP0338200)

MOL for NP0338200 (Ethyl icosapentate)

3D MOL for NP0338200 (Ethyl icosapentate)

3D SDF for NP0338200 (Ethyl icosapentate)

3D-SDF for NP0338200 (Ethyl icosapentate)

PDB for NP0338200 (Ethyl icosapentate)

3D PDB for NP0338200 (Ethyl icosapentate)

SMILES for NP0338200 (Ethyl icosapentate)

INCHI for NP0338200 (Ethyl icosapentate)

Structure for NP0338200 (Ethyl icosapentate)

3D Structure for NP0338200 (Ethyl icosapentate)