Showing Compound Card for Isolinolenic acid (CDB000378)

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Record Information
Version1.0
Created at2020-03-19 00:33:53 UTC
Updated at2020-12-07 19:07:24 UTC
CannabisDB IDCDB000378
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsolinolenic acid
Description9E,11E-Octadecadienoic acid, also known as (e,e)-isolinoleic acid or (9E,11E)-9,11-octadecadienoate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Conjugated linoleic acid (CLA) is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. 9E,11E-Octadecadienoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 9E,11E-Octadecadienoic acid has been detected in milk and dairy products (from cow) and red meat. This could make 9E,11E-octadecadienoic acid a potential biomarker for the consumption of these foods. Isolinolenic acid is one of many unsaturated fatty acids that have been identified in the oil of cannabis seeds (PMID: 6991645 ). Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation, and obesity. More recent human CLA-supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, after supplementation with the trans-10, cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. Contemporary dietary recommendations tend to limit red meat and dairy products and the possible CLA deficiencies must be compensated with dietary supplements. However, with human studies, a specific dietary pattern that controls and includes CLA has not been established. As a result, differences among studies and among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity of the participants may also impact these studies (PMID: 17053429 , 17217167 , 17554969 , 16477173 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9E,11E)-9,11-Octadecadienoic acidChEBI
(e,e)-9,11-Octadecadienoic acidChEBI
(e,e)-Isolinoleic acidChEBI
9-trans, 11-trans-CLAChEBI
9-trans,11-trans-Conjugated linoleic acidChEBI
9-trans,11-trans-Octadecadienoic acidChEBI
9E,11E-CLAChEBI
9t,11t-CLAChEBI
Conjugated (9E,11E)-linoleic acidChEBI
Isolinoleic acidChEBI
Mangold's acidChEBI
trans,trans-9,11-Octadecadienoic acidChEBI
trans-9, trans-11-Octadecadienoic acidChEBI
(9E,11E)-9,11-OctadecadienoateGenerator
(e,e)-9,11-OctadecadienoateGenerator
(e,e)-IsolinoleateGenerator
9-trans,11-trans-Conjugated linoleateGenerator
9-trans,11-trans-OctadecadienoateGenerator
Conjugated (9E,11E)-linoleateGenerator
IsolinoleateGenerator
trans,trans-9,11-OctadecadienoateGenerator
trans-9, trans-11-OctadecadienoateGenerator
(9E,11E)-OctadecadienoateGenerator
9,11-Linoleic acidHMDB, MeSH
CLA 80HMDB
Conjugated linoleic acidHMDB
delta9,11-OctadecadienoateHMDB
Nouracid de 554HMDB
Ricineic acidHMDB
Ricinenic acidHMDB
Selin claHMDB
9,11-Linoleic acid, (E,E)-isomerMeSH, HMDB
9,11-Isolinoleic acidMeSH, HMDB
Octadeca-9,11-dienoic acidMeSH, HMDB
9,11-OctadecadienoateMeSH, HMDB
(9E,11E)-Octadecadienoic acidHMDB
9,11-Conjugated linoleic acidHMDB
9-trans,11-trans-Linoleic acidHMDB
9E,11E-Octadecadienoic acidHMDB
FA(18:2(9E,11E))HMDB
delta9,11-Octadecadienoic acidHMDB
trans-11-trans-9-Octadecadienoic acidHMDB
trans-9,trans-11 Conjugated linoleic acidHMDB
trans-9,trans-11-Octadecadienoic acidHMDB
Δ9,11-Octadecadienoic acidHMDB
9E,11E-OctadecadienoateGenerator
10E,12Z-OctadecadienoateGenerator
Chemical FormulaC18H32O2
Average Molecular Weight280.45
Monoisotopic Molecular Weight280.2402
IUPAC Name(9E,11E)-octadeca-9,11-dienoic acid
Traditional Name9E,11E-octadecadienoic acid
CAS Registry Number1839-11-8
SMILES
CCCCCC\C=C\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+
InChI KeyJBYXPOFIGCOSSB-XBLVEGMJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • 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
Physiological effect

Health effect:

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
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.11ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability37.12 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-MSIsolinolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9550000000-f91f775c11691e572339Spectrum
Predicted GC-MSIsolinolenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9531000000-ff0f0a6283e777000b03Spectrum
Predicted GC-MSIsolinolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-d3517fc9c425686f3f472017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dfad2b4819a8e09aeb742017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0093020000-3713e3e16e9fc8ff9d4e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-1ab95baf25a47f7edbbe2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-88b67552039f5c14c7ea2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-d3517fc9c425686f3f472017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dfad2b4819a8e09aeb742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-1ab95baf25a47f7edbbe2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-d3517fc9c425686f3f472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dfad2b4819a8e09aeb742021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-1ab95baf25a47f7edbbe2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-f2c6c9de24118516f0db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-5690000000-f4c090f44fe34f660b192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-42ee75da80e6ee682b902017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c962017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-b43315d97b9995f922a32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-5590000000-6740409ad0ee9d0c387c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-9510000000-78bd3b0ecfca1dab2bac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apm-9000000000-98f6af2debd76c0c3c6e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d027662021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-c03baa3d5c1c48e8c45c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-07f427d77d98dab09f402021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005047
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023610
KNApSAcK IDC00053367
Chemspider ID4445923
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282796
PDB IDNot Available
ChEBI ID88464
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Toomey S, McMonagle J, Roche HM: Conjugated linoleic acid: a functional nutrient in the different pathophysiological components of the metabolic syndrome? Curr Opin Clin Nutr Metab Care. 2006 Nov;9(6):740-7. doi: 10.1097/01.mco.0000247465.34037.05. [PubMed:17053429 ]
  3. Navarro V, Fernandez-Quintela A, Churruca I, Portillo MP: The body fat-lowering effect of conjugated linoleic acid: a comparison between animal and human studies. J Physiol Biochem. 2006 Jun;62(2):137-47. doi: 10.1007/BF03174074. [PubMed:17217167 ]
  4. Tvrzicka E, Vecka M, Zak A: [Conjugated linoleic acid--the dietary supplement in the prevention of cardiovascular diseases]. Cas Lek Cesk. 2007;146(5):459-65. [PubMed:17554969 ]
  5. Tricon S, Yaqoob P: Conjugated linoleic acid and human health: a critical evaluation of the evidence. Curr Opin Clin Nutr Metab Care. 2006 Mar;9(2):105-10. doi: 10.1097/01.mco.0000214567.44568.fb. [PubMed:16477173 ]