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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, 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
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
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 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti methicillin-resistant Staphylococcus aureus33282 An agent that targets and inhibits the growth of methicillin-resistant Staphylococcus aureus (MRSA), a bacterium responsible for severe infections. Therapeutically, it is used to treat MRSA-related infections, reducing the risk of complications and mortality, and is commonly used in hospitals to prevent the spread of MRSA.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti plasmodial33281 An agent that inhibits the growth of Plasmodium parasites, reducing malaria symptoms. Therapeutically, it's used to treat and prevent malaria, with key medical applications including prophylaxis and treatment of malaria infections.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
TrypanocideAn agent that kills trypanosomes, used to treat diseases like African sleeping sickness and Chagas disease, caused by Trypanosoma parasites, reducing parasitic infections and associated symptoms.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— 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.