Showing metabocard for Eicosapentaenoic acid (BMDB0001999)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:43 UTC
Update Date2020-06-04 21:12:35 UTC
MCDB ID BMDB0001999
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
MOLSDFPDBSMILESInChI
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9700000000-09ea61ed836b882050282014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-9700000000-09ea61ed836b882050282017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5490000000-ee15446245c5d0190ca22017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adr-9462000000-6310373b498d395ee4b12017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0029000000-02c67e3601df249d24762017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-1f183f43649d7b5d2f922021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2987000000-6239462e49ad0240cfd92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-028a784c6c5a01da151c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000x-9600000000-177a8f3f229d3ffe1c4f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0039000000-41dbbfbea0e69ff3303d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2988000000-6239462e49ad0240cfd92021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1196000000-2fd0631ba34b61c028232016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-5891000000-6b514ce76e6321b59f492016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8950000000-5f7ac71eb4fd77059c962016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-63f4108595227b77b5f02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-c196324eb61e1a26da902016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-844643f720715a477b352016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-da419ae96bb8b07031de2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-2179000000-483c2cd6dc1d5799c3e42021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9530000000-b5f6ca6a7368abde88262021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-3985000000-f0a1f1db5a552a3146892021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-5910000000-a82843e1aa65987b4a172021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9600000000-da4dd030385c445969bc2021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-05ox-9400000000-567226e93d65502352cd2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1124 +/- 463 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified958 +/- 330 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable details
Detected and Quantified33 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified330 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified992 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified1653 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
HMDB IDHMDB0001999
DrugBank IDDB00159
Phenol Explorer Compound IDNot Available
FoodDB 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.