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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:05 UTC
Update Date2022-03-07 02:52:46 UTC
HMDB IDHMDB0030963
Secondary Accession Numbers
  • HMDB30963
Metabolite Identification
Common NamePunicic acid
DescriptionPunicic acid, also known as 9t,11C,13t-CLN or punicate, 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. Based on a literature review a significant number of articles have been published on Punicic acid.
Structure
Data?1563862064
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
(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
PunicateGenerator
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acidHMDB
cis-9,trans-11,cis-13-Octadecatrienoic acidHMDB
Eleostearic acidHMDB
Punicinic acidHMDB
Trichosanic acidHMDB
9E,11Z,13E-OctadecatrienoateGenerator
9,11,13-CLNMeSH
9C,11t,13t-CLNMeSH
Eleostearic acid, (e,Z,e)-isomerMeSH
9,11,13-Octadecatrienoic acidMeSH
9cis,11trans,13trans-Conjugated linolenic acidMeSH
Eleostearic acid, (e,e,e)-isomerMeSH
9,11,13-Conjugated linolenic acidMeSH
Eleostearic acid, (Z,e,e)-isomerMeSH
Eleostearic acid, (Z,Z,e)-isomerMeSH
a-EleostearateGenerator
a-Eleostearic acidGenerator
alpha-EleostearateGenerator
Α-eleostearateGenerator
Α-eleostearic acidGenerator
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
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
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point44 - 45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.024 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.60931661259
DarkChem[M-H]-177.71831661259
DeepCCS[M+H]+176.03230932474
DeepCCS[M-H]-173.67430932474
DeepCCS[M-2H]-207.72830932474
DeepCCS[M+Na]+183.13630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Punicic acidCCCC\C=C\C=C/C=C/CCCCCCCC(O)=O3610.3Standard polar33892256
Punicic acidCCCC\C=C\C=C/C=C/CCCCCCCC(O)=O2186.6Standard non polar33892256
Punicic acidCCCC\C=C\C=C/C=C/CCCCCCCC(O)=O2309.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Punicic acid,1TMS,isomer #1CCCC/C=C/C=C\C=C\CCCCCCCC(=O)O[Si](C)(C)C2358.6Semi standard non polar33892256
Punicic acid,1TBDMS,isomer #1CCCC/C=C/C=C\C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2584.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Punicic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8960000000-59c083671232b201abc82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Punicic acid GC-MS (1 TMS) - 70eV, Positivesplash10-009j-8922000000-a833082a5dc1b9b8fef62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Punicic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 10V, Negative-QTOFsplash10-004i-0090000000-9017290211373e0fd9682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 20V, Negative-QTOFsplash10-0059-1090000000-f71ec81e19ca9b6622af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-97b44baaf23d3bde3d462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 10V, Negative-QTOFsplash10-004i-0090000000-12da14b99ffff52801582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 20V, Negative-QTOFsplash10-056r-1090000000-e58964825ceee9b9ae452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 40V, Negative-QTOFsplash10-052f-9510000000-6e24c220dbce17f77c3e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 10V, Positive-QTOFsplash10-01t9-0090000000-88ce0b28b56f5ae5db9d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 20V, Positive-QTOFsplash10-02u0-6590000000-30f95b4c2d9566284c4e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 40V, Positive-QTOFsplash10-014l-8930000000-fe0898dc5088e651e2202016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 10V, Positive-QTOFsplash10-01t9-4690000000-76ea346646e2d3f7b75c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 20V, Positive-QTOFsplash10-0536-9810000000-b47f33760bad1f74f7dc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicic acid 40V, Positive-QTOFsplash10-05ox-9100000000-f5a89343e9ef6aafee092021-09-24Wishart LabView Spectrum
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
FooDB IDFDB012466
KNApSAcK IDC00001216
Chemspider ID20118304
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Eleostearic acid
METLIN IDNot Available
PubChem Compound12309425
PDB IDNot Available
ChEBI ID38383
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588761
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.. .