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Record Information
Version4.0
Creation Date2008-09-16 13:19:52 UTC
Update Date2017-09-27 08:26:15 UTC
HMDB IDHMDB0010378
Secondary Accession Numbers
  • HMDB10378
Metabolite Identification
Common Name5,8,11-Eicosatrienoic acid
Description5,8,11-Eicosatrienoic acid (Mead acid) is a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3(n-9). In the presence of lipoxygenase, Mead acid can form various hydroxy products (HETE). It is the only polyunsaturated fatty acid that the body can make de novo. Its elevated presence in the blood is an indication of essential fatty acid (EFA)deficiency. During dietary EFA insufficiency, especially arachidonic acid deficiency, the body will make Mead acid by the elongation and desaturation of oleic acid. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acidChEBI
(5Z,8Z,11Z)-Eicosatrienoic acidChEBI
5Z,8Z,11Z-Eicosatrienoic acidChEBI
5Z,8Z,11Z-Icosatrienoic acidChEBI
all-cis-Eicosa-5,8,11-trienoic acidChEBI
all-cis-Icosa-5,8,11-trienoic acidChEBI
C20:3N-9,12,15ChEBI
ETrE(5Z,8Z,11Z)ChEBI
Mead acidChEBI
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoateGenerator
(5Z,8Z,11Z)-EicosatrienoateGenerator
5Z,8Z,11Z-EicosatrienoateGenerator
5Z,8Z,11Z-IcosatrienoateGenerator
all-cis-Eicosa-5,8,11-trienoateGenerator
all-cis-Icosa-5,8,11-trienoateGenerator
5,8,11-Eicosatrienoic acidMeSH
ETrA acidMeSH
Chemical FormulaC20H34O2
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
IUPAC Name(5Z,8Z,11Z)-icosa-5,8,11-trienoic acid
Traditional Namemead acid
CAS Registry Number20590-32-3
SMILES
CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(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/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-
InChI KeyUNSRRHDPHVZAHH-YOILPLPUSA-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:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.3e-05 g/LALOGPS
logP7.35ALOGPS
logP6.95ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m³·mol⁻¹ChemAxon
Polarizability39.08 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-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 Quantified0.012 +/- 2.910 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.987 +/- 0.45 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.274 +/- 4.372 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.316 +/- 1.365 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 IDFDB027529
KNApSAcK IDNot Available
Chemspider ID4471956
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312531
PDB IDNot Available
ChEBI ID1306412
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available