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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:05 UTC
Update Date2018-03-12 22:08:02 UTC
HMDB IDHMDB0030963
Secondary Accession Numbers
  • HMDB30963
Metabolite Identification
Common NamePunicic acid
Description9E,11Z,13E-Octadecatrienoic acid, also known as 9t,11C,13t-CLN or 9t,11C,13t-conjugated linolenic acid, 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. 9E,11Z,13E-Octadecatrienoic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, 9E,11Z,13E-octadecatrienoic acid is primarily located in the membrane (predicted from logP). Outside of the human body, 9E,11Z,13E-octadecatrienoic acid can be found in fats and oils, fruits, and pomegranate. This makes 9E,11Z,13E-octadecatrienoic acid a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(9E,11Z,13E)-9,11,13-Octadecatrienoic acidChEBI
(e,Z,e)-9,11,13-Octadecatrienoic acidChEBI
9-trans,11-cis,13-trans-Octadecatrienoic acidChEBI
9t,11C,13t-CLNChEBI
9t,11C,13t-CLnAChEBI
9t,11C,13t-Conjugated linolenic acidChEBI
9t,11C,13t-Linolenic acidChEBI
9trans,11-cis,13trans-Octadecatrienoic acidChEBI
C18:3 N-5 trans, 7 cis, 9 transChEBI
Octadeca-9t,11C,13t-trienoic acidChEBI
Octadeca-9t,11C,13t-triensaeureChEBI
t9,C11,t13-CLNChEBI
t9,C11,t13-CLnAChEBI
t9,C11,t13-Conjugated linolenic acidChEBI
t9,C11,t13-Linolenic acidChEBI
(9E,11Z,13E)-9,11,13-OctadecatrienoateGenerator
PunicateGenerator
(e,Z,e)-9,11,13-OctadecatrienoateGenerator
9-trans,11-cis,13-trans-OctadecatrienoateGenerator
9t,11C,13t-Conjugated linolenateGenerator
9t,11C,13t-LinolenateGenerator
9trans,11-cis,13trans-OctadecatrienoateGenerator
Octadeca-9t,11C,13t-trienoateGenerator
t9,C11,t13-Conjugated linolenateGenerator
t9,C11,t13-LinolenateGenerator
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acidHMDB
cis-9,trans-11,cis-13-Octadecatrienoic acidHMDB
Eleostearic acidHMDB
Punicinic acidHMDB
Trichosanic acidHMDB
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(9E,11Z,13E)-octadeca-9,11,13-trienoic acid
Traditional Name9t,11c,13t-linolenic acid
CAS Registry Number544-72-9
SMILES
CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+
InChI KeyCUXYLFPMQMFGPL-MRZTUZPCSA-N
Chemical Taxonomy
DescriptionThis compound 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
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acyl
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44 - 45 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.65ALOGPS
logP6.06ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability35.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8960000000-59c083671232b201abc8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009j-8922000000-a833082a5dc1b9b8fef6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0090000000-88ce0b28b56f5ae5db9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u0-6590000000-30f95b4c2d9566284c4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-8930000000-fe0898dc5088e651e220View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-9017290211373e0fd968View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-f71ec81e19ca9b6622afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-97b44baaf23d3bde3d46View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012466
KNApSAcK IDC00001216
Chemspider ID20118304
KEGG Compound IDC08364
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPunicic acid
METLIN IDNot Available
PubChem Compound12309425
PDB IDNot Available
ChEBI ID38383
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Du Plessis LM: Isomerization of the double bonds of a conjugated fatty acid during beta-oxidation. Lipids. 1979 Nov;14(11):943-8. [PubMed:513983 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .