Record Information
Version1.0
Creation date2010-04-08 22:04:53 UTC
Update date2020-02-24 19:10:21 UTC
Primary IDFDB001230
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePunicafolin
DescriptionPunicafolin 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. Punicafolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Punicafolin has been detected, but not quantified in, fruits and pomegranates. This could make punicafolin a potential biomarker for the consumption of these foods.
CAS Number88847-11-4
Structure
Thumb
Synonyms
SynonymSource
1,2,4-Tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-b-D-glucopyranoseHMDB
6,7,8,11,12,13-Hexahydroxy-3,16-dioxo-21,22-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-23-yl 3,4,5-trihydroxybenzoic acidGenerator
Punicafolindb_source
Predicted Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
logP3.32ALOGPS
logP4.26ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.29ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area444.18 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity213.83 m³·mol⁻¹ChemAxon
Polarizability83.39 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC41H30O26
IUPAC name6,7,8,11,12,13-hexahydroxy-3,16-dioxo-22,23-bis(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)64-33-23-9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(8-22(49)30(54)32(25)56)40(61)65-34(33)35(66-37(58)11-3-17(44)27(51)18(45)4-11)41(63-23)67-38(59)12-5-19(46)28(52)20(47)6-12/h1-8,23,33-35,41-56H,9H2
InChI KeyDPBVYZVSXAZMAY-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC(C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight938.6613
Monoisotopic Molecular Weight938.102531132
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
  • Pentacarboxylic acid or derivatives
  • Macrolide
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.46%; H 3.22%; O 44.32%DFC
Melting PointMp 235-237° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -59.5 (c, 0.4 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy0-0704516905-5080ee8668e635d06d54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0921001603-62fcd0a40a80d44731f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul0-0931500100-e7988b38d5eccc4c32bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0300000926-9d0cec2910cddb7b2ddbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0901022511-6ec3cdc428cbd79b5fe8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-1ee4d37707a6fa76ee52Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5320800
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29950
CRC / DFC (Dictionary of Food Compounds) IDLMS49-B:BWV05-M
EAFUS IDNot Available
Dr. Duke IDPUNICAFOLIN
BIGG IDNot Available
KNApSAcK IDNot Available
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Takashi Tanaka, Gen-Ichiro Nonaka, and Itsuo Nishioka, “Punicafolin, an ellagitannin from the leaves of Punica granatum,” Phytochemistry 24, no. 9 (1985): 2075-2078. [No PubMed ID] PDF [Isolation]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).