Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2015-07-20 21:49:46 UTC
Primary IDFDB002945
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePunicic acid
DescriptionFound in pomegranate oil (Punica granatum) Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 (n-5). It is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil. It is also found in the seed oils of snake gourd and bitter gourd.; Punicic acid is a conjugated linolenic acid or ClnA; i.e. it has three conjugated double bonds. It is chemically similar to the conjugated linoleic acids, or CLA, which have two. In lab rats, it was found that punicic acid was converted to the CLA rumenic acid (9Z11E-CLA). In vitro, it shows anticancer activity against prostate cancer cells. OLETF rats?a strain which becomes obese?remained relatively lean when punicic acid was added to their feed. Fat cells undergo programmed cell death when exposed to punicic acid from bitter-gourd oil.
CAS Number544-72-9
Structure
Thumb
Synonyms
SynonymSource
(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
9E,11Z,13E-OctadecatrienoateGenerator
PunicateHMDB
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acidHMDB
cis-9,trans-11,cis-13-Octadecatrienoic acidHMDB
Eleostearic acidHMDB
Punicinic acidHMDB
Trichosanic acidHMDB
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
(9Z,11E,13Z)-octadeca-9,11,13-trienoic acidbiospider
Punicic aciddb_source
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
Chemical FormulaC18H30O2
IUPAC name(9E,11Z,13E)-octadeca-9,11,13-trienoic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCC\C=C\C=C/C=C/CCCCCCCC(O)=O
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.65%; H 10.86%; O 11.49%DFC
Melting PointMp 44-45°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data287 () (cyclohexane)DFC
DensityNot Available
Refractive IndexNot Available
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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08364
Pubchem Compound ID5281126
Pubchem Substance IDNot Available
ChEBI ID8638
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHHC08-L:CPM11-G
EAFUS IDNot Available
Dr. Duke IDPUNICIC-ACID|PUNICIC-ACID-(CIS-9,TRANS-11,CIS-13-OCTADECATRIENOIC-ACID)
BIGG IDNot Available
KNApSAcK IDC00001236
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPunicic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti eicosanoid35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.