Showing metabocard for 8,11,14,17-Eicosatetraenoic acid (BMDB0002177)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:08 UTC
Update Date2020-06-04 21:09:28 UTC
MCDB ID BMDB0002177
Secondary Accession Numbers
  • BMDB02177
Metabolite Identification
Common Name8,11,14,17-Eicosatetraenoic acid
Description8,11,14,17-Eicosatetraenoic acid 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. 8,11,14,17-Eicosatetraenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, 8,11,14,17-eicosatetraenoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8,11,14,17-EicosatetraenoateGenerator
8,11,14,17-Eicosatetraenoic acidMeSH
8,11,14,17-Eicosatetraenoic acid, Z-isomerMeSH
Chemical FormulaC20H32O2
Average Molecular Weight304.474
Monoisotopic Molecular Weight304.24023027
IUPAC Name(8E,11E,14E,17E)-icosa-8,11,14,17-tetraenoic acid
Traditional Name(8E,11E,14E,17E)-icosa-8,11,14,17-tetraenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)/b4-3+,7-6+,10-9+,13-12+
InChI KeyHQPCSDADVLFHHO-GFRMADBLSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.83ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability38.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0092000000-adcd16a168a2136833fa2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4691000000-5b06d9f96470dd7ccef92019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052n-8950000000-6129946446ff6f7126332019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-057a58eb03c1d61d43f92019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1095000000-a5e878ae7122108346ea2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-d349b1db215c158d4b052019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1116 +/- 459 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified952 +/- 328 uMTotal fatty acid
  • M. Ferrand et al....
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound5282842
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  2. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.