Showing metabocard for 11,14,17-Eicosatrienoic acid (BMDB0060039)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:41:27 UTC
Update Date2020-06-04 21:03:00 UTC
MCDB ID BMDB0060039
Secondary Accession Numbers
  • BMDB60039
Metabolite Identification
Common Name11,14,17-Eicosatrienoic acid
Description11,14,17-Eicosatrienoic acid, also known as 20:3, N-3,6,9 all-cis or ETA, 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. 11,14,17-Eicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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 Weight306.4828
Monoisotopic Molecular Weight306.255880332
IUPAC Name(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Traditional Nameeicosatrienoic acid
CAS Registry Number17046-59-2
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-4960000000-ee31f077045fbc10d0c62017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022a-8972000000-11b27d7266369b9ebc182017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03dr-0090000000-d8dffe611cf00f7d9e6d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-89a04280ae844b3d1c1e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-5591000000-d0a16956780551b951782016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-8950000000-64dfe5d75f4f453c6c312016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-d10c7c1b109440c211362016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2089000000-0abcc3d67afb5981b6d42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-fda7effe116a88cc975f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-4596000000-995657b9029281236c8e2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-9820000000-87f7e85d00d036dc52d22021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-eea6b43bb6e346821f502021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-a547ddaba8c204ad4b7f2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1069000000-c4949e5e0cfdc4b33b862021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-30310e4351623257055d2021-10-12View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1109 +/- 457 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified946 +/- 326 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
HMDB IDHMDB0060039
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006293
KNApSAcK IDNot Available
Chemspider ID4471954
KEGG Compound IDC16522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312529
PDB IDNot Available
ChEBI ID53460
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). 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. Metabolomics.
  2. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). 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. Chemometrics and Intelligent Laboratory Systems.