Punicafolin (CHEM023570)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:09:14 UTC
Update Date2016-11-09 01:17:44 UTC
Accession NumberCHEM023570
Identification
Common NamePunicafolin
ClassSmall Molecule
DescriptionIsolated from the leaf of Punica granatum (pomegranate). Punicafolin is found in fruits and pomegranate.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC41H30O26
Average Molecular Mass938.661 g/mol
Monoisotopic Mass938.103 g/mol
CAS Registry Number88847-11-4
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
Traditional 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
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy0-0704516905-5080ee8668e635d06d54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0921001603-62fcd0a40a80d44731f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul0-0931500100-e7988b38d5eccc4c32bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0300000926-9d0cec2910cddb7b2ddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0901022511-6ec3cdc428cbd79b5fe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-1ee4d37707a6fa76ee52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ri-0100020419-2f5d14d9f65c7e598c53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0far-1900010484-badb2f12c5a33ccc17fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-2900121241-beda1774d8eb11fc603dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0300000609-626aeac928729fec02d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gbi-0901000225-09273f8bc5778fa89e36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-3900001171-16d7ed4b35f00fccb3eaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029950
FooDB IDFDB001230
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPunicafolin
Chemspider ID417252
ChEBI IDNot Available
PubChem Compound ID475273
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
2. Takashi Tanaka, Gen-Ichiro Nonaka, and Itsuo Nishioka: Punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry 24, no. 9 (1985): 2075-2078. [Isolation]