Record Information
Version1.0
Creation date2010-04-08 22:13:54 UTC
Update date2019-11-26 03:16:35 UTC
Primary IDFDB018735
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePunicalin
DescriptionPunicalin 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. Punicalin is an extremely weak basic (essentially neutral) compound (based on its pKa). Punicalin is found, on average, in the highest concentration within pomegranates. Punicalin has also been detected, but not quantified in, fruits. This could make punicalin a potential biomarker for the consumption of these foods.
CAS Number65995-64-4
Structure
Thumb
Synonyms
SynonymSource
PunicalinMeSH
4,6-Gallagylglucosedb_source
Predicted Properties
PropertyValueSource
Water Solubility4.32 g/LALOGPS
logP2.09ALOGPS
logP1.5ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area377.42 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity176.22 m³·mol⁻¹ChemAxon
Polarizability69.3 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC34H22O22
IUPAC name(10S,11R,12R,15R)-3,4,5,11,12,13,21,22,23,26,27,38,39-tridecahydroxy-9,14,17,29,36-pentaoxaoctacyclo[29.8.0.0^{2,7}.0^{10,15}.0^{19,24}.0^{25,34}.0^{28,33}.0^{32,37}]nonatriaconta-1(31),2(7),3,5,19,21,23,25(34),26,28(33),32(37),38-dodecaene-8,18,30,35-tetrone
InChI IdentifierInChI=1S/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1
InChI KeyIQHIEHIKNWLKFB-OBOTWMKHSA-N
Isomeric SMILESOC1O[C@@H]2COC(=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)O[C@H]2[C@H](O)[C@H]1O
Average Molecular Weight782.5253
Monoisotopic Molecular Weight782.060272388
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
  • Gallic acid or derivatives
  • Coumarin
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Hemiacetal
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.19%; H 2.83%; O 44.98%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 -81.1 (c, 0.6 in H2O)DFC
Spectroscopic UV Data329 (e 14125) (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, Positivesplash10-00lr-0000000900-d43238e73ab352190728Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ldr-0000000900-542c5f8d98f3346a460cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0py0-0000003900-f4c1052f02a4c9cfdbf2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0000002900-18dfaf19efa50dec18b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gwr-2000000900-ef40b5feb7b3c9a6ed99Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h0s-1000009300-95432b30828166824ab2Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5464368
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39205
CRC / DFC (Dictionary of Food Compounds) IDLMN20-N:LMN20-N
EAFUS IDNot Available
Dr. Duke IDPUNICALIN
BIGG IDNot Available
KNApSAcK IDC00037699
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID925
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti AIDS22587 A substance that destroys or inhibits replication of viruses.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
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.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
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.