Showing metabocard for Eicosadienoic acid (BMDB0005060)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:08 UTC
Update Date2020-06-04 20:33:30 UTC
MCDB ID BMDB0005060
Secondary Accession Numbers
  • BMDB05060
Metabolite Identification
Common NameEicosadienoic acid
DescriptionEicosadienoic acid, also known as 11,14-eicosadienoate or delta11,14-20:2, 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. Eicosadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Eicosadienoic acid has been found to be associated with the diseases known as colorectal cancer; also eicosadienoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z,14Z)-Eicosa-11,14-dienoic acidChEBI
(11Z,14Z)-Eicosadienoic acidChEBI
(11Z,14Z)-Icosa-11,14-dienoic acidChEBI
11,14-Eicosadienoic acidChEBI
11,14-Icosadienoic acidChEBI
(11Z,14Z)-Eicosa-11,14-dienoateGenerator
(11Z,14Z)-EicosadienoateGenerator
(11Z,14Z)-Icosa-11,14-dienoateGenerator
11,14-EicosadienoateGenerator
11,14-IcosadienoateGenerator
EicosadienoateGenerator
11, 14-IcosadienoateHMDB
11, 14-Icosadienoic acidHMDB
11,14-trans-Eicosadienoic acidHMDB
delta11,14-20:2HMDB
Eicosa-11,14-dienoic acidHMDB
Eicosa-11,14-dienoic acid, (Z,Z)-isomerHMDB
N-6 Eicosadienoic acidHMDB
DihomolinoleateHMDB
(11Z,14Z)-IcosadienoateHMDB
(11Z,14Z)-11,14-EicosadienateHMDB
(11Z,14Z)-11,14-Eicosadienic acidHMDB
(11Z,14Z)-11,14-EicosadienoateHMDB
(11Z,14Z)-11,14-Eicosadienoic acidHMDB
11,14-all-cis-EicosadienoateHMDB
11,14-all-cis-Eicosadienoic acidHMDB
11-cis,14-cis-EicosadienoateHMDB
11-cis,14-cis-Eicosadienoic acidHMDB
BishomolinoleateHMDB
Bishomolinoleic acidHMDB
Dihomo-linoleate (20:2n6)HMDB
Dihomo-linoleic acid (20:2n6)HMDB
FA(20:2(11Z,14Z))HMDB
Homo-gamma-linoleateHMDB
Homo-gamma-linoleic acidHMDB
Homo-γ-linoleateHMDB
Homo-γ-linoleic acidHMDB
all-cis-11,14-EicosadienoateHMDB
all-cis-11,14-Eicosadienoic acidHMDB
cis,cis-Eicosa-11,14-dienoateHMDB
cis,cis-Eicosa-11,14-dienoic acidHMDB
cis,cis-delta11,14-EicosadienoateHMDB
cis,cis-delta11,14-Eicosadienoic acidHMDB
cis,cis-Δ11,14-eicosadienoateHMDB
cis,cis-Δ11,14-eicosadienoic acidHMDB
cis-11,cis-14-EicosadienoateHMDB
cis-11,cis-14-Eicosadienoic acidHMDB
delta11,14-EicosadienoateHMDB
delta11,14-Eicosadienoic acidHMDB
Δ11,14-eicosadienoateHMDB
Δ11,14-eicosadienoic acidHMDB
FA(20:2n6)HMDB
Eicosadienoic acidChEBI
Chemical FormulaC20H36O2
Average Molecular Weight308.4986
Monoisotopic Molecular Weight308.271530396
IUPAC Name(11Z,14Z)-icosa-11,14-dienoic acid
Traditional Nameeicosadienoic acid
CAS Registry Number2091-39-6
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-
InChI KeyXSXIVVZCUAHUJO-HZJYTTRNSA-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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.251Not Available
Predicted Properties
PropertyValueSource
logP7.83ALOGPS
logP7.31ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity97.72 m³·mol⁻¹ChemAxon
Polarizability39.94 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, Positivesplash10-0006-9760000000-cd3039251f27ed6598332017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9652000000-051c308924d68202698f2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View 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 , negativesplash10-000i-0091000000-cd5567f72a97a19a5daa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-26edae55398bbe6d8f142020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-003v-9200000000-f117dd4d613f97c9e9a12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003u-9100000000-64feb0d0359edf0e55fa2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-003u-9100000000-1c5be01a2863610157562020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-005c-9100000000-2af5db21026406ee4f512020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 44V, positivesplash10-005c-9100000000-900bb2bb1942a2772e062020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-05o0-1900000000-87b112cb6d02616a73902020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0009000000-66380db5e2f48c28d9142020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0009000000-37933ac7549ff468e6e02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0019000000-139b1c14ace1228062062020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0049000000-bea23a8f63f68b2a25792020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-052g-3594000000-9f6dd586ee4aa178e78e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0hka-0930000000-500174f550638fdb0b032020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-0490000000-80d1e0e8b9b35e1634502020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-cf7b1131f470250aedcb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0006-0090000000-32033519d24a370bbb6e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-2590000000-f57018cf6f280ddd27bd2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059w-7930000000-7f2165e3d0add956aa592020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-053s-9600000000-4f5ff0e39e1f3cb65e882020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-053s-9300000000-8f9cd251a7bb707f15442020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-001m-9100000000-176d923c10fc2cf41b6c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-1890000000-ea581730d6da2112857d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-014i-9000000000-1170a17e0bd60829ce3f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-001i-9000000000-3e1931835afb9d465af42020-07-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2561 +/- 616 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2431 +/- 518 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0005060
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012619
KNApSAcK IDNot Available
Chemspider ID4944228
KEGG Compound IDC16525
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439848
PDB IDNot Available
ChEBI ID73731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  2. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
  3. 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.
  4. 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.