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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 13:19:52 UTC
Update Date2020-05-08 23:04:30 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
Data?1582752821
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-EicosatrienoateGenerator
ETrA acidHMDB
5,8,11-Eicosatrienoic acidMeSH, HMDB
(5Z,8Z,11Z)-IcosatrienoateGenerator
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
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9270000000-463f91799534dd9ba1f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0209-9241000000-4adccb37d26c8a88baafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0092000000-602cfb1975c490e3881aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-3490000000-1350ff64ed6aa1f5820aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mp-9860000000-d900ed087b26c9530957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0039000000-659857ef79dd2148ca8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1095000000-43d44a6c226a6b2adffeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-3585933dc08c1124a8e8Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.095 +/- 0.012 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
BloodDetected and Quantified10.7 +/- 4.4 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.3 +/- 3.8 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease References
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312531
PDB IDNot Available
ChEBI ID72865
Food Biomarker OntologyNot Available
VMH IDM02457
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available