Livestock Metabolome Database: Showing metabocard for Eicosapentaenoic acid (LMDB00369)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:18 UTC

Update Date

2016-09-23 18:45:16 UTC

Lmdb

LMDB00369

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Eicosapentaenoic acid

Description

Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an 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. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, 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. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3 and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in animal breast milk. -- Wikipedia.

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.

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

omega-3 fatty acid (CHEBI:28364 )
icosapentaenoic acid (CHEBI:28364 )
Unsaturated fatty acids (C06428 )
Polyunsaturated fatty acids (C06428 )
Liner triterpenes (C06428 )
Unsaturated fatty acids (LMFA01030759 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

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	6.53	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	35.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004l-9700000000-09ea61ed836b88205028	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-9700000000-09ea61ed836b88205028	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5490000000-ee15446245c5d0190ca2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0adr-9462000000-6310373b498d395ee4b1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0029000000-02c67e3601df249d2476	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-1f183f43649d7b5d2f92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2987000000-6239462e49ad0240cfd9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-028a784c6c5a01da151c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9600000000-177a8f3f229d3ffe1c4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0039000000-41dbbfbea0e69ff3303d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2988000000-6239462e49ad0240cfd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-1196000000-2fd0631ba34b61c02823	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-5891000000-6b514ce76e6321b59f49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8950000000-5f7ac71eb4fd77059c96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-63f4108595227b77b5f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2079000000-c196324eb61e1a26da90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-844643f720715a477b35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-da419ae96bb8b07031de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-2179000000-483c2cd6dc1d5799c3e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9530000000-b5f6ca6a7368abde8826	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-3985000000-f0a1f1db5a552a314689	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-5910000000-a82843e1aa65987b4a17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9600000000-da4dd030385c445969bc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05ox-9400000000-567226e93d65502352cd	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Muscle
Oocyte
Oocyte (zona-intact oocytes)

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected but not Quantified	Not Applicable	Not Available	Porcine	Warzych, E., Cies...	details
Milk	Detected and Quantified	10 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	100 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	300 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	500 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Muscle	Detected but not Quantified	Not Applicable	Not Available	Bovine	23871026	details
Oocyte	Detected but not Quantified	Not Applicable	Not Available	Ovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Bovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details