Record Information
Version1.0
Creation date2011-09-21 01:25:56 UTC
Update date2018-05-29 01:54:13 UTC
Primary IDFDB027529
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number20590-32-3
Structure
Thumb
Synonyms
SynonymSource
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoateGenerator
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acidChEBI
(5Z,8Z,11Z)-EicosatrienoateGenerator
(5Z,8Z,11Z)-Eicosatrienoic acidChEBI
(Z,Z,Z)-5,8,11-Eicosatrienoatehmdb
(Z,Z,Z)-5,8,11-Eicosatrienoic acidhmdb
5,8,11-Eicosatrienoatehmdb
5,8,11-Eicosatrienoic acidhmdb
5Z,8Z,11Z-Eicosatrienoatehmdb
5Z,8Z,11Z-Eicosatrienoic acidhmdb
5Z,8Z,11Z-IcosatrienoateGenerator
5Z,8Z,11Z-Icosatrienoic acidChEBI
all-cis-5,8,11-Eicosatrienoatehmdb
all-cis-5,8,11-Eicosatrienoic acidhmdb
all-cis-Eicosa-5,8,11-trienoateGenerator
all-cis-Eicosa-5,8,11-trienoic acidChEBI
all-cis-Icosa-5,8,11-trienoateGenerator
all-cis-Icosa-5,8,11-trienoic acidChEBI
C20:3N-9,12,15ChEBI
cis-5,8,11-Eicosatrienoatehmdb
cis-5,8,11-Eicosatrienoic acidhmdb
ETrE(5Z, 8Z, 11Z)hmdb
ETrE(5Z,8Z,11Z)ChEBI
Mead acidhmdb
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
Polarizability39.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H34O2
IUPAC nameicosa-5,8,11-trienoic acid
InChI IdentifierInChI=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)
InChI KeyUNSRRHDPHVZAHH-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCC=CCC=CCC=CCCCC(O)=O
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
Classification
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4471956
ChEMBL IDCHEMBL1865841
KEGG Compound IDNot Available
Pubchem Compound ID5312531
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10378
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference