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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-23 11:28:21 UTC
Update Date2017-10-23 19:04:15 UTC
HMDB IDHMDB0005060
Secondary Accession Numbers
  • HMDB05060
Metabolite Identification
Common NameEicosadienoic acid
DescriptionEicosadienoic acid is an omega 6 fatty acid found in human 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
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
EicosadienoateGenerator
(11Z,14Z)-EicosadienoateGenerator
(11Z,14Z)-Icosa-11,14-dienoateGenerator
11,14-EicosadienoateGenerator
11,14-IcosadienoateGenerator
11, 14-IcosadienoateHMDB
11, 14-Icosadienoic acidHMDB
11,14-trans-Eicosadienoic acidMeSH
delta11,14-20:2MeSH
Eicosa-11,14-dienoic acidMeSH
Eicosa-11,14-dienoic acid, (e,e)-isomerMeSH
Eicosa-11,14-dienoic acid, (Z,Z)-isomerMeSH
Eicosa-11,14-dienoic acid, ion (1-)MeSH
N-6 Eicosadienoic acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.251Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
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
Polarizability39.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9760000000-cd3039251f27ed659833View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9652000000-051c308924d68202698fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0091000000-cd5567f72a97a19a5daaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0092000000-bcb4dbfbca4a66a8f89aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kd-4591000000-8359fe54412fa3b34e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-9850000000-1ce6afea317e415a6b1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0039000000-46defe7a3a5473b710fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1096000000-42d4303cc1fdabc4e3c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-5622f571522f8f140346View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.418 +/- 0.162 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified15.0730 +/- 4.182 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.352 +/- 0.029 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite 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 ID603631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:15256803 ]
  2. Lipid Maps (LMFA01030130) [Link]