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Record Information
Version3.6
Creation Date2012-09-11 17:33:45 UTC
Update Date2013-06-30 11:36:48 UTC
HMDB IDHMDB29950
Secondary Accession NumbersNone
Metabolite Identification
Common NamePunicafolin
DescriptionPunicafolin is found in fruits. Punicafolin is isolated from the leaf of Punica granatum (pomegranate) Punicafolin belongs to the family of Hydrolyzable Tannins. These are tannins whose structure is characterized by either ofthe following models: (1) contains galloyl units are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units, (2) contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
Structure
Thumb
Synonyms
  1. 1,2,4-Tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-b-D-glucopyranose
  2. Punicafolin
Chemical FormulaC41H30O26
Average Molecular Weight938.6613
Monoisotopic Molecular Weight938.102531132
IUPAC Name6,7,8,11,12,13-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-trihydroxybenzoate
Traditional IUPAC Name6,7,8,11,12,13-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-trihydroxybenzoate
CAS Registry Number88847-11-4
SMILES
OC1=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 Identifier
InChI=1/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-UHFFFAOYNA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassTannins
ClassHydrolyzable Tannins
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Tannins
Substituents
  • 1,2 Diphenol
  • Benzoate
  • Benzoyl
  • Carboxylic Acid Ester
  • Gallic Acid Derivative
  • Hydroxybenzoic Acid
  • Lactone
  • Macrolide
  • Oxane
  • Phenol
  • Phenol Derivative
  • Pyrogallol Derivative
  • Resorcinol
  • Tricarboxylic Acid Derivative
Direct ParentHydrolyzable Tannins
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
BiofunctionNot Available
Application
  • Nutrient
Cellular locations
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point235 - 237 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 Charge-1ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area444.18ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity213.83ChemAxon
Polarizability83.39ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001230
KNApSAcK IDNot Available
Chemspider ID417252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB29950
Metagene LinkHMDB29950
METLIN IDNot Available
PubChem Compound475273
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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]