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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2022-03-07 02:49:13 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
Data?1582752233
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
(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
cis-8,11,14,17-EicosatetraenoateGenerator
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-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
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
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available187.333http://allccs.zhulab.cn/database/detail?ID=AllCCS00001908
[M+H]+Not Available178.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00001908
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.91331661259
DarkChem[M-H]-183.40231661259
DeepCCS[M+H]+180.72830932474
DeepCCS[M-H]-178.3730932474
DeepCCS[M-2H]-211.25730932474
DeepCCS[M+Na]+186.82130932474
AllCCS[M+H]+182.832859911
AllCCS[M+H-H2O]+179.832859911
AllCCS[M+NH4]+185.632859911
AllCCS[M+Na]+186.432859911
AllCCS[M-H]-183.432859911
AllCCS[M+Na-2H]-185.232859911
AllCCS[M+HCOO]-187.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cis-8,11,14,17-Eicosatetraenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O3738.9Standard polar33892256
Cis-8,11,14,17-Eicosatetraenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O2160.6Standard non polar33892256
Cis-8,11,14,17-Eicosatetraenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O2332.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cis-8,11,14,17-Eicosatetraenoic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C2385.2Semi standard non polar33892256
Cis-8,11,14,17-Eicosatetraenoic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C2627.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-6790000000-9f82428f04530524e4d22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01w0-7962000000-84eacc6d7a7ceee0c99a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0090000000-ac340d2fdec1962255512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , positive-QTOFsplash10-002f-0591000000-9c83feea251cbef18bac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , positive-QTOFsplash10-059m-0491000000-c78942db68649dad37052017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Positive-QTOFsplash10-052r-0092000000-adcd16a168a2136833fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Positive-QTOFsplash10-0a4r-4691000000-e3736249247ab6a172282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Positive-QTOFsplash10-052n-8950000000-af9e1166c7a23305f6452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Negative-QTOFsplash10-0udi-0039000000-057a58eb03c1d61d43f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Negative-QTOFsplash10-0zg0-1095000000-a5e878ae7122108346ea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9240000000-d349b1db215c158d4b052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Negative-QTOFsplash10-0udi-0019000000-e301ae96559ee65daa0e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Negative-QTOFsplash10-0udr-2069000000-b0db6033219193d0d9e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Negative-QTOFsplash10-006x-9320000000-58917ba5f6a9872149492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Positive-QTOFsplash10-0a4r-4796000000-26f15a5b60f20cad946e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Positive-QTOFsplash10-001l-7910000000-dcb9693160ae6a462cd82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Positive-QTOFsplash10-0036-9300000000-a07065b94af0ab13e4262021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDEICOSTET
MarkerDB IDNot Available
Good Scents 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. [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 ]