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Record Information
Version1.0
Creation Date2016-09-30 22:49:43 UTC
Update Date2020-06-04 21:12:35 UTC
BMDB IDBMDB0001999
Secondary Accession Numbers
  • BMDB01999
Metabolite Identification
Common NameEicosapentaenoic acid
DescriptionEicosapentaenoic acid, also known as icosapent or cis-5,8,11,14,17-epa, 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. Eicosapentaenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Eicosapentaenoic acid participates in a number of enzymatic reactions, within cattle. In particular, Eicosapentaenoic acid can be biosynthesized from cis-8,11,14,17-eicosatetraenoic acid; which is mediated by the enzyme fatty acid desaturase 1. In addition, Eicosapentaenoic acid can be converted into docosapentaenoic acid (22N-3); which is mediated by the enzyme elongation OF very long chain fatty acids protein 5. In cattle, eicosapentaenoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Eicosapentaenoic acid has been found to be associated with several diseases known as colorectal cancer, essential hypertension, hypertension, and major depressive disorder; also eicosapentaenoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACIDChEBI
5,8,11,14,17-Icosapentaenoic acidChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acidChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acidChEBI
cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
cis-5,8,11,14,17-EPAChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acidChEBI
EPAChEBI
IcosapentChEBI
Icosapentaenoic acidChEBI
IcosapentoChEBI
IcosapentumChEBI
Timnodonic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-IcosapentaenoateKegg
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EicosapentaenoateGenerator
(all-Z)-5,8,11,14,17-EicosapentaenoateGenerator
5,8,11,14,17-EICOSAPENTAENOateGenerator
5,8,11,14,17-IcosapentaenoateGenerator
all-cis-5,8,11,14,17-EicosapentaenoateGenerator
all-cis-Icosa-5,8,11,14,17-pentaenoateGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoateGenerator
cis-5,8,11,14,17-EicosapentaenoateGenerator
cis-delta(5,8,11,14,17)-EicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoic acidGenerator
IcosapentaenoateGenerator
TimnodonateGenerator
5Z,8Z,11Z,14Z,17Z-EicosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoateGenerator
EicosapentaenoateGenerator
Omega-3-eicosapentaenoic acidHMDB
Acid, eicosapentanoicHMDB
Eicosapentanoic acidHMDB
Omega 3 eicosapentaenoic acidHMDB
all-cis-IcosapentaenoateHMDB
all-cis-Icosapentaenoic acidHMDB
(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acidHMDB
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acidHMDB
(all-Z)-Δ5,8,11,14,17-eicosapentaenoic acidHMDB
(all-cis)-5,8,11,14,17-Eicosapentaenoic acidHMDB
FA(20:5(5Z,8Z,11Z,14Z,17Z))HMDB
FA(20:5n3)HMDB
Eicosapentaenoic acidHMDB
Chemical FormulaC20H30O2
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Nameeicosapentaenoic acid
CAS Registry Number10417-94-4
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 KeyJAZBEHYOTPTENJ-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m³·mol⁻¹ChemAxon
Polarizability35.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9700000000-09ea61ed836b88205028View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-9700000000-09ea61ed836b88205028View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5490000000-ee15446245c5d0190ca2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adr-9462000000-6310373b498d395ee4b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0029000000-02c67e3601df249d2476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1196000000-2fd0631ba34b61c02823View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-5891000000-6b514ce76e6321b59f49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8950000000-5f7ac71eb4fd77059c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-63f4108595227b77b5f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-c196324eb61e1a26da90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-844643f720715a477b35View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05ox-9400000000-567226e93d65502352cdView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Leukocyte
  • Liver
  • Milk
  • Muscle
  • Oocyte
  • Placenta
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueDetected and Quantified348.62 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified199.31 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified33.0632 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified330.632 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified991.896 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified1653.16 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified1124.149 +/- 462.885 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified958.833 +/- 330.632 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001999
DrugBank IDDB00159
Phenol Explorer Compound IDNot Available
FooDB IDFDB030126
KNApSAcK IDC00001215
Chemspider ID393682
KEGG Compound IDC06428
BioCyc IDEICOSAPENTAENOATE
BiGG ID2218016
Wikipedia LinkEicosapentaenoic acid
METLIN ID6423
PubChem Compound446284
PDB IDNot Available
ChEBI ID28364
References
Synthesis ReferenceSandri, Jacqueline; Viala, Jacques. Syntheses of all-(Z)-5,8,11,14,17-Eicosapentaenoic Acid and all-(Z)-4,7,10,13,16,19-Docosahexaenoic Acid from (Z)-1,1,6,6-tetraisopropoxy-3-hexene. Journal of Organic Chemistry (1995), 60(20), 6627-30.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  3. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
  4. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
  5. M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.

Enzymes

General function:
Not Available
Specific function:
Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:
ELOVL5
Uniprot ID:
Q2KJD9
Molecular weight:
35377.0
Reactions
Eicosapentaenoic acid → Clupanodonic aciddetails