You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Cis-8,11,14,17-Eicosatetraenoic acid (HMDB0002177)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
Creation Date2006-05-22 14:17:39 UTC
Update Date2017-09-27 08:24:13 UTC
HMDB IDHMDB0002177
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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
cis-8,11,14,17-EicosatetraenoateGenerator
(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
8,11,14,17-Eicosatetraenoic acid, Z-isomerMeSH
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 KeyHQPCSDADVLFHHO-LTKCOYKYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 Solubility0.00016 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability37.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-ac340d2fdec196225551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-002f-0591000000-9c83feea251cbef18bacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-059m-0491000000-c78942db68649dad3705View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-adcd16a168a2136833faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4691000000-e3736249247ab6a17228View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052n-8950000000-af9e1166c7a23305f645View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-057a58eb03c1d61d43f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1095000000-a5e878ae7122108346eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-d349b1db215c158d4b05View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Alpha Linolenic Acid and Linoleic Acid MetabolismPw000006Pw000006 greyscalePw000006 simpleMap00592
Displaying 1 entry
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 IDCPD-8121
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11722594
PDB IDNot Available
ChEBI ID71488
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. [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 ]