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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2020-02-26 21:23:53 UTC
Secondary Accession Numbers
  • HMDB02177
Metabolite Identification
Common NameCis-8,11,14,17-Eicosatetraenoic acid
DescriptionCis-8,11,14,17-Eicosatetraenoic acid is an eicosanoid present in marine lipids, a minor n-3 polyunsaturated fatty acid (PUFA) which is a position isomer of 20:4n-6. n-3 PUFA contained in marine lipids appear to have a protective effect against coronary heart disease and thrombosis. Human platelets metabolize 8,11,14,17-eicosatetraenoic acid primarily into 12-hydroxy-8,10,14,17-eicosatetraenoic acid. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. Taken together, these findings indicate that the enzymatic conversion of eicosatrienoic acid to specific signaling molecules can occur in the nucleus, that it is regulated, and that the synthesized products may act within the nucleus. PMID: 3109494 , 8142566 , 16574479 , 15896193 , 10037447 ). Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils.
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoic acidChEBI
(8Z,11Z,14Z,17Z)-Eicosatetraenoic acidChEBI
(8Z,11Z,14Z,17Z)-Icosatetraenoic acidChEBI
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoic acidChEBI
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoic acidChEBI
8Z,11Z,14Z,17Z-Eicosatetraenoic acidChEBI
all-cis-8,11,14,17-Eicosatetraenoic acidChEBI
all-Z-8,11,14,17-Eicosatetraenoic acidChEBI
all-Z-8,11,14,17-Icosatetraenoic acidChEBI
Omega-3-arachidonic acidChEBI
8, 11, 14, 17-IcosatetraenoateHMDB
8, 11, 14, 17-Icosatetraenoic acidHMDB
8,11,14,17-Eicosatetraenoic acidHMDB
8,11,14,17-Eicosatetraenoic acid, Z-isomerHMDB
Chemical FormulaC20H32O2
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
IUPAC Name(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
Traditional Name(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
CAS Registry Number2091-26-1
InChI Identifier
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
  • 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

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00016 g/LALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability37.35 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-6790000000-9f82428f04530524e4d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01w0-7962000000-84eacc6d7a7ceee0c99aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-ac340d2fdec196225551Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-002f-0591000000-9c83feea251cbef18bacSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-059m-0491000000-c78942db68649dad3705Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-adcd16a168a2136833faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4691000000-e3736249247ab6a17228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052n-8950000000-af9e1166c7a23305f645Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-057a58eb03c1d61d43f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1095000000-a5e878ae7122108346eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-d349b1db215c158d4b05Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified0.007 (0 - 0.014) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022887
KNApSAcK IDNot Available
Chemspider ID9897310
KEGG Compound IDNot Available
BioCyc IDCPD-8121
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11722594
PDB IDNot Available
ChEBI ID71488
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Careaga MM, Sprecher H: Metabolism of 8,11,14,17-eicosatetraenoic acid by human platelet lipoxygenase and cyclooxygenase. Biochim Biophys Acta. 1987 Jul 13;920(1):94-101. [PubMed:3109494 ]
  2. Loick HM, Theissen JL: [Eicosanoids as mediators in ARDS]. Anasthesiol Intensivmed Notfallmed Schmerzther. 1994 Feb;29(1):3-9. [PubMed:8142566 ]
  3. Luo M, Flamand N, Brock TG: Metabolism of arachidonic acid to eicosanoids within the nucleus. Biochim Biophys Acta. 2006 May-Jun;1761(5-6):618-25. Epub 2006 Mar 20. [PubMed:16574479 ]
  4. Charbeneau RP, Peters-Golden M: Eicosanoids: mediators and therapeutic targets in fibrotic lung disease. Clin Sci (Lond). 2005 Jun;108(6):479-91. [PubMed:15896193 ]
  5. Croset M, Bordet JC, Lagarde M: Inhibition of prostaglandin H synthase and activation of 12-lipoxygenase by 8,11,14,17-eicosatetraenoic acid in human endothelial cells and platelets. Biochem Pharmacol. 1999 Mar 15;57(6):631-8. [PubMed:10037447 ]