Showing Compound Card for Eicosadienoic acid (CDB005776)

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Record Information
Version1.0
Created at2020-04-27 16:55:27 UTC
Updated at2020-12-07 19:12:11 UTC
CannabisDB IDCDB005776
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEicosadienoic acid
DescriptionEicosadienoic acid, also known as eicosadienoate, belongs to the class of organic compounds known as long-chain fatty acids. It is a naturally occurring omega-6 fatty acid found in human milk. Omega-6 fatty acids are a family of unsaturated fatty acids which have a carbon-carbon double bond in the n‚àí6 position in common, that is, the sixth bond from the end of the fatty acid. These are unbranched fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Eicosadienic acid is a weakly acidic compound (based on its pKa). Fatty acid biosynthesis occurs through the acetate pathway and the process is catalyzed by the Fatty Acid Synthase (FAS). Structurally, FAS varies significantly across different organisms but essentially, they all perform the same task using the same mechanisms. Eicosadienoic acid has been detected in black walnut and it is one of several fatty acids that are known in cannabis plants (PMID: 28448475 ). Eicosadienoic acid is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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
(11Z,14Z)-EicosadienoateGenerator
(11Z,14Z)-Icosa-11,14-dienoateGenerator
11,14-EicosadienoateGenerator
11,14-IcosadienoateGenerator
EicosadienoateGenerator
11, 14-IcosadienoateHMDB
11, 14-Icosadienoic acidHMDB
11,14-trans-Eicosadienoic acidHMDB
delta11,14-20:2HMDB
Eicosa-11,14-dienoic acidHMDB
Eicosa-11,14-dienoic acid, (Z,Z)-isomerHMDB
N-6 Eicosadienoic acidHMDB
DihomolinoleateHMDB
(11Z,14Z)-IcosadienoateHMDB
(11Z,14Z)-11,14-EicosadienateHMDB
(11Z,14Z)-11,14-Eicosadienic acidHMDB
(11Z,14Z)-11,14-EicosadienoateHMDB
(11Z,14Z)-11,14-Eicosadienoic acidHMDB
11,14-all-cis-EicosadienoateHMDB
11,14-all-cis-Eicosadienoic acidHMDB
11-cis,14-cis-EicosadienoateHMDB
11-cis,14-cis-Eicosadienoic acidHMDB
BishomolinoleateHMDB
Bishomolinoleic acidHMDB
Dihomo-linoleate (20:2n6)HMDB
Dihomo-linoleic acid (20:2n6)HMDB
FA(20:2(11Z,14Z))HMDB
Homo-gamma-linoleateHMDB
Homo-gamma-linoleic acidHMDB
Homo-γ-linoleateHMDB
Homo-γ-linoleic acidHMDB
all-cis-11,14-EicosadienoateHMDB
all-cis-11,14-Eicosadienoic acidHMDB
cis,cis-Eicosa-11,14-dienoateHMDB
cis,cis-Eicosa-11,14-dienoic acidHMDB
cis,cis-delta11,14-EicosadienoateHMDB
cis,cis-delta11,14-Eicosadienoic acidHMDB
cis,cis-Δ11,14-eicosadienoateHMDB
cis,cis-Δ11,14-eicosadienoic acidHMDB
cis-11,cis-14-EicosadienoateHMDB
cis-11,cis-14-Eicosadienoic acidHMDB
delta11,14-EicosadienoateHMDB
delta11,14-Eicosadienoic acidHMDB
Δ11,14-eicosadienoateHMDB
Δ11,14-eicosadienoic acidHMDB
FA(20:2n6)HMDB
Eicosadienoic acidChEBI
Chemical FormulaC20H36O2
Average Molecular Weight308.5
Monoisotopic Molecular Weight308.2715
IUPAC Name(11Z,14Z)-icosa-11,14-dienoic acid
Traditional Nameeicosadienoic acid
CAS Registry Number5598-38-9
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
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:

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
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
Polarizability39.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEicosadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9760000000-cd3039251f27ed659833Spectrum
Predicted GC-MSEicosadienoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9652000000-051c308924d68202698fSpectrum
Predicted GC-MSEicosadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEicosadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0091000000-cd5567f72a97a19a5daa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-26edae55398bbe6d8f142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-003v-9200000000-f117dd4d613f97c9e9a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003u-9100000000-64feb0d0359edf0e55fa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-003u-9100000000-1c5be01a2863610157562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-005c-9100000000-2af5db21026406ee4f512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 44V, positivesplash10-005c-9100000000-900bb2bb1942a2772e062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-05o0-1900000000-87b112cb6d02616a73902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0009000000-66380db5e2f48c28d9142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0009000000-37933ac7549ff468e6e02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0019000000-139b1c14ace1228062062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0049000000-bea23a8f63f68b2a25792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-052g-3594000000-9f6dd586ee4aa178e78e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0hka-0930000000-500174f550638fdb0b032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-0490000000-80d1e0e8b9b35e1634502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-cf7b1131f470250aedcb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0006-0090000000-32033519d24a370bbb6e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-2590000000-f57018cf6f280ddd27bd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059w-7930000000-7f2165e3d0add956aa592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-053s-9600000000-4f5ff0e39e1f3cb65e882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-053s-9300000000-8f9cd251a7bb707f15442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-001m-9100000000-176d923c10fc2cf41b6c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-1890000000-ea581730d6da2112857d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-014i-9000000000-1170a17e0bd60829ce3f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-001i-9000000000-3e1931835afb9d465af42020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005060
DrugBank IDNot Available
Phenol Explorer Compound 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 ID73731
References
General References
  1. Mikulcova V, Kasparkova V, Humpolicek P, Bunkova L: Formulation, Characterization and Properties of Hemp Seed Oil and Its Emulsions. Molecules. 2017 Apr 27;22(5). pii: molecules22050700. doi: 10.3390/molecules22050700. [PubMed:28448475 ]