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Showing Compound Punicalagin (FDB016425)

Record Information
Version1.0
Creation date2010-04-08 22:12:25 UTC
Update date2019-11-26 03:13:13 UTC
Primary IDFDB016425
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePunicalagin
DescriptionConstituent of Punica granatum (pomegranate) Punicalagin is the major tannin component of Terminalia catappa and have been characterized to possess antioxidative and anti-genotoxic activities. ; T. catappa has been a popular folk medicine for preventing hepatoma and treating hepatitis in Taiwan; the leaves contain many hydrolyzable tannins. Although the leaves of T. catappa have been claimed to be effective in preventing hepatoma, the mechanism of its chemopreventive effect remains to be elucidated, and their effects on reactive oxygen species (ROS) mediated carcinogenesis are still unclear. (PMID: 16242868). Punicalagin is found in fruits and pomegranate.
CAS Number65995-63-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,3-(S)-Hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucosebiospider
2,3-(S)-Hexahydroxydiphenoyl-4,6-(S,S)-gallagylglucosedb_source
Predicted Properties
PropertyValueSource
Water Solubility2.06 g/LALOGPS
logP3.24ALOGPS
logP3.94ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area510.94 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity246.82 m³·mol⁻¹ChemAxon
Polarizability94.85 ųChemAxon
Number of Rings11ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC48H28O30
IUPAC name6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.0^{4,9}.0^{10,19}.0^{13,18}.0^{16,25}.0^{17,22}.0^{26,31}.0^{38,55}.0^{41,46}.0^{47,52}]pentapentaconta-4(9),5,7,10,12,16(25),17(22),18,23,26(31),27,29,41,43,45,47(52),48,50-octadecaene-3,15,20,32,40,53-hexone
InChI IdentifierInChI=1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2
InChI KeyZJVUMAFASBFUBG-UHFFFAOYSA-N
Isomeric SMILESOC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C4C(=O)OC5=C6C(C(=O)OC(C(O)=C3O)=C46)=C(C(O)=C5O)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC12
Average Molecular Weight1084.7179
Monoisotopic Molecular Weight1084.066539556
Classification
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Ellagic_acid
  • 7,8-dihydroxycoumarin
  • Tetracarboxylic acid or derivatives
  • Gallic acid or derivatives
  • Isocoumarin
  • Coumarin
  • Benzopyran
  • 2-benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Hemiacetal
  • Lactone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 53.15%; H 2.60%; O 44.25%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]28D +3.8 (c, 0.9 in MeOH)DFC
Spectroscopic UV Data375 (e 12200) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9000000000-bc4c702ee30fc822936f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9001101201-6a1917b915e25ff05e502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9653148001-badb3a71eae23668c6782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ktr-9003205100-7243d10443d57493c72b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aos-9020123000-a0d6f5ff3b5b9cd8fea52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0029032003-655df1f6b1240384469e2016-08-03View Spectrum
NMRNot Available
ChemSpider ID17216347
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22833653
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID449
DrugBank IDNot Available
HMDB IDHMDB05795
CRC / DFC (Dictionary of Food Compounds) IDKRC12-H:KRC12-H
EAFUS IDNot Available
Dr. Duke IDPUNICALAGIN
BIGG IDNot Available
KNApSAcK IDC00035378
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPunicalagin
Phenol-Explorer Metabolite ID449
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
trypanocideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.