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Record Information
Version3.6
Creation Date2006-05-22 14:17:39 UTC
Update Date2016-02-11 01:05:25 UTC
HMDB IDHMDB02177
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
ValueSource
(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
ETAChEBI
Omega-3-arachidonic acidChEBI
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoateGenerator
all-cis-8,11,14,17-IcosatetraenoateGenerator
(8Z,11Z,14Z,17Z)-EicosatetraenoateGenerator
(8Z,11Z,14Z,17Z)-IcosatetraenoateGenerator
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoateGenerator
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoateGenerator
8Z,11Z,14Z,17Z-EicosatetraenoateGenerator
all-cis-8,11,14,17-EicosatetraenoateGenerator
all-Z-8,11,14,17-EicosatetraenoateGenerator
all-Z-8,11,14,17-IcosatetraenoateGenerator
Omega-3-arachidonateGenerator
8, 11, 14, 17-IcosatetraenoateHMDB
8, 11, 14, 17-Icosatetraenoic acidHMDB
8,11,14,17-EicosatetraenoateHMDB
8,11,14,17-Eicosatetraenoic acidHMDB
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
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-
InChI KeyInChIKey=HQPCSDADVLFHHO-LTKCOYKYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000165 mg/mLALOGPS
logP6.83ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m3·mol-1ChemAxon
Polarizability37.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022887
KNApSAcK IDNot Available
Chemspider ID9897310
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02177
Metagene LinkHMDB02177
METLIN IDNot Available
PubChem Compound11722594
PDB IDNot Available
ChEBI IDNot Available
References
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. [3109494 ]
  2. Loick HM, Theissen JL: [Eicosanoids as mediators in ARDS]. Anasthesiol Intensivmed Notfallmed Schmerzther. 1994 Feb;29(1):3-9. [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. [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. [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. [10037447 ]