11,14,17-Eicosatrienoic acid (CHEM022809)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:54:42 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022809
Identification
Common Name11,14,17-Eicosatrienoic acid
ClassSmall Molecule
DescriptionAn icosatrienoic acid having three cis- double bonds at positions 11, 14 and 17.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acidChEBI
(11Z,14Z,17Z)-Icosa-11,14,17-trienoic acidChEBI
(Z,Z,Z)-11,14,17-Eicosatrienoic acidChEBI
11,14,17-Eicosatrienoic acidChEBI
11,14,17-Icosatrienoic acidChEBI
11C,14C,17C-Eicosatrienoic acidChEBI
11C,14C,17C-EicosatriensaeureChEBI
20:3, N-3,6,9 all-cisChEBI
all-cis-11,14,17-Eicosatrienoic acidChEBI
all-cis-Eicosa-11,14,17-trienoic acidChEBI
all-cis-Eicosa-11,14,17-triensaeureChEBI
C20:3, N-3,6,9 all-cisChEBI
cis,cis,cis-11,14,17-Eicosatrienoic acidChEBI
Eicosa-11Z,14Z,17Z-trienoic acidChEBI
Eicosatrienoic acidChEBI
ETAChEBI
ETEChEBI
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoateGenerator
(11Z,14Z,17Z)-Icosa-11,14,17-trienoateGenerator
(Z,Z,Z)-11,14,17-EicosatrienoateGenerator
11,14,17-EicosatrienoateGenerator
11,14,17-IcosatrienoateGenerator
11C,14C,17C-EicosatrienoateGenerator
all-cis-11,14,17-EicosatrienoateGenerator
all-cis-Eicosa-11,14,17-trienoateGenerator
cis,cis,cis-11,14,17-EicosatrienoateGenerator
Eicosa-11Z,14Z,17Z-trienoateGenerator
EicosatrienoateGenerator
Dihomo-a-linolenateGenerator
Dihomo-a-linolenic acidGenerator
Dihomo-alpha-linolenateGenerator
Dihomo-α-linolenateGenerator
Dihomo-α-linolenic acidGenerator
DihomolinolenateHMDB
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomerHMDB
Bishomo-a-linolenateHMDB
Bishomo-a-linolenic acidHMDB
Bishomo-alpha-linolenateHMDB
Bishomo-α-linolenateHMDB
Bishomo-α-linolenic acidHMDB
Bishomo-alpha-linolenic acidHMDB
Dihomo-linolenateHMDB
Dihomo-linolenic acidHMDB
Dihomolinolenic acidHMDB
FA(20:3(11Z,14Z,17Z))HMDB
FA(20:3n3)HMDB
Homo-alpha-linolenic acidHMDB
Homo-α-linolenic acidHMDB
Dihomo-alpha-linolenic acidHMDB
Chemical FormulaC20H34O2
Average Molecular Mass306.483 g/mol
Monoisotopic Mass306.256 g/mol
CAS Registry NumberNot Available
IUPAC Name(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Traditional Nameeicosatrienoic acid
SMILESCC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-
InChI KeyAHANXAKGNAKFSK-PDBXOOCHSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.7e-05 g/LALOGPS
logP7.24ALOGPS
logP6.95ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-4960000000-ee31f077045fbc10d0c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022a-8972000000-11b27d7266369b9ebc18Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03dr-0090000000-d8dffe611cf00f7d9e6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-89a04280ae844b3d1c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-5591000000-d0a16956780551b95178Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-8950000000-64dfe5d75f4f453c6c31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-d10c7c1b109440c21136Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2089000000-0abcc3d67afb5981b6d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-fda7effe116a88cc975fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-4596000000-995657b9029281236c8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-9820000000-87f7e85d00d036dc52d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-eea6b43bb6e346821f50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-a547ddaba8c204ad4b7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1069000000-c4949e5e0cfdc4b33b86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-30310e4351623257055dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060039
FooDB IDFDB006293
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4471954
ChEBI ID53460
PubChem Compound ID5312529
Kegg Compound IDC16522
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=196185
2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
3. 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
4. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. The lipid handbook with CD-ROM