Back to Compounds

Showing Compound Dihomolinolenic acid (FDB006293)

Record Information
Version1.0
Creation date2010-04-08 22:07:04 UTC
Update date2025-11-18 23:01:29 UTC
Primary IDFDB006293
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihomolinolenic acid
DescriptionDihomolinolenic acid, also known as 11,14,17-eicosatrienoic acid or (11z,14z,17z)-eicosa-11,14,17-trienoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, dihomolinolenic acid is considered to be a fatty acid lipid molecule. Dihomolinolenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Dihomolinolenic acid can be found in evening primrose, which makes dihomolinolenic acid a potential biomarker for the consumption of this food product. Dihomolinolenic acid can be found primarily in blood and feces.
CAS Number17046-59-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acidChEBI
(11Z,14Z,17Z)-Icosa-11,14,17-trienoic acidChEBI
(Z,Z,Z)-11,14,17-Eicosatrienoic acidChEBI
11,14,17-Eicosatrienoic acidChEBI
11,14,17-Icosatrienoic acidChEBI
11C,14C,17C-Eicosatrienoic acidChEBI
11C,14C,17C-EicosatriensaeureChEBI
20:3, N-3,6,9 all-cisChEBI
all-cis-11,14,17-Eicosatrienoic acidChEBI
all-cis-Eicosa-11,14,17-trienoic acidChEBI
all-cis-Eicosa-11,14,17-triensaeureChEBI
C20:3, N-3,6,9 all-cisChEBI
cis,cis,cis-11,14,17-Eicosatrienoic acidChEBI
Eicosa-11Z,14Z,17Z-trienoic acidChEBI
Eicosatrienoic acidChEBI
ETAChEBI
ETEChEBI
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoateGenerator
(11Z,14Z,17Z)-Icosa-11,14,17-trienoateGenerator
(Z,Z,Z)-11,14,17-EicosatrienoateGenerator
11,14,17-EicosatrienoateGenerator
11,14,17-IcosatrienoateGenerator
11C,14C,17C-EicosatrienoateGenerator
all-cis-11,14,17-EicosatrienoateGenerator
all-cis-Eicosa-11,14,17-trienoateGenerator
cis,cis,cis-11,14,17-EicosatrienoateGenerator
Eicosa-11Z,14Z,17Z-trienoateGenerator
EicosatrienoateGenerator
Dihomo-a-linolenateGenerator
Dihomo-a-linolenic acidGenerator
Dihomo-alpha-linolenateGenerator
Dihomo-α-linolenateGenerator
Dihomo-α-linolenic acidGenerator
DihomolinolenateHMDB
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomerHMDB
Bishomo-a-linolenateHMDB
Bishomo-a-linolenic acidHMDB
Bishomo-alpha-linolenateHMDB
Bishomo-α-linolenateHMDB
Bishomo-α-linolenic acidHMDB
Bishomo-alpha-linolenic acidHMDB
Dihomo-linolenateHMDB
Dihomo-linolenic acidHMDB
Dihomolinolenic acidHMDB
FA(20:3(11Z,14Z,17Z))HMDB
FA(20:3n3)HMDB
Homo-alpha-linolenic acidHMDB
Homo-α-linolenic acidHMDB
Dihomo-alpha-linolenic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility7.7e-05 g/LALOGPS
logP7.24ALOGPS
logP6.95ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O2
IUPAC name(11Z,14Z,17Z)-icosa-11,14,17-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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-
InChI KeyAHANXAKGNAKFSK-PDBXOOCHSA-N
Isomeric SMILESCC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
Classification
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

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDihomolinolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-4960000000-ee31f077045fbc10d0c6Spectrum
Predicted GC-MSDihomolinolenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-022a-8972000000-11b27d7266369b9ebc18Spectrum
Predicted GC-MSDihomolinolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03dr-0090000000-d8dffe611cf00f7d9e6d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-89a04280ae844b3d1c1e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-5591000000-d0a16956780551b951782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-8950000000-64dfe5d75f4f453c6c312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-d10c7c1b109440c211362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2089000000-0abcc3d67afb5981b6d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-fda7effe116a88cc975f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-4596000000-995657b9029281236c8e2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-9820000000-87f7e85d00d036dc52d22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-eea6b43bb6e346821f502021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-a547ddaba8c204ad4b7f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1069000000-c4949e5e0cfdc4b33b862021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-30310e4351623257055d2021-10-12View Spectrum
NMRNot Available
ChemSpider ID4471954
ChEMBL IDCHEMBL453991
KEGG Compound IDC16522
Pubchem Compound ID5312529
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0060039
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDDIHOMO-LINOLENIC-ACID
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).