Showing metabocard for Eicosadienoic acid (LMDB00460)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:50:21 UTC
Update Date2016-09-23 18:45:32 UTC
LmdbLMDB00460
Secondary Accession NumbersNone
Metabolite Identification
Common NameEicosadienoic acid
DescriptionEicosadienoic acid is an omega 6 fatty acid found in animal milk (PMID: 15256803 ). Omega-6 fatty acids) are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the omega−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body.
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
logP7.83ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9760000000-cd3039251f27ed659833Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9652000000-051c308924d68202698fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0091000000-cd5567f72a97a19a5daaSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-26edae55398bbe6d8f14Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-003v-9200000000-f117dd4d613f97c9e9a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003u-9100000000-64feb0d0359edf0e55faSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-003u-9100000000-1c5be01a286361015756Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-005c-9100000000-2af5db21026406ee4f51Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 44V, positivesplash10-005c-9100000000-900bb2bb1942a2772e06Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-05o0-1900000000-87b112cb6d02616a7390Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0009000000-66380db5e2f48c28d914Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0009000000-37933ac7549ff468e6e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0019000000-139b1c14ace122806206Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0049000000-bea23a8f63f68b2a2579Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-052g-3594000000-9f6dd586ee4aa178e78eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0hka-0930000000-500174f550638fdb0b03Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-0490000000-80d1e0e8b9b35e163450Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-cf7b1131f470250aedcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0006-0090000000-32033519d24a370bbb6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-2590000000-f57018cf6f280ddd27bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059w-7930000000-7f2165e3d0add956aa59Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-053s-9600000000-4f5ff0e39e1f3cb65e88Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-053s-9300000000-8f9cd251a7bb707f1544Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-001m-9100000000-176d923c10fc2cf41b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-1890000000-ea581730d6da2112857dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-014i-9000000000-1170a17e0bd60829ce3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-001i-9000000000-3e1931835afb9d465af4Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
  • Oocyte
  • Oocyte (zona-intact oocytes)
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
 details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
OocyteDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailableBovine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0005060
FooDB IDFDB012619
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4944228
ChEBI ID73731
PubChem Compound ID6439848
Kegg Compound IDC16525
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Minda H, Kovacs A, Funke S, Szasz M, Burus I, Molnar S, Marosvolgyi T, Decsi T: Changes of fatty acid composition of human milk during the first month of lactation: a day-to-day approach in the first week. Ann Nutr Metab. 2004;48(3):202-9. Epub 2004 Jul 13. [15256803 ]