Record Information
Version1.0
Creation date2010-04-08 22:13:54 UTC
Update date2019-11-26 03:16:34 UTC
Primary IDFDB018728
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePunicacortein A
DescriptionPunicacortein A 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. Punicacortein A is an extremely weak basic (essentially neutral) compound (based on its pKa). Punicacortein A is found, on average, in the highest concentration within pomegranates. Punicacortein A has also been detected, but not quantified in, fruits. This could make punicacortein a a potential biomarker for the consumption of these foods.
CAS Number103488-35-3
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility4.5 g/LALOGPS
logP1.48ALOGPS
logP0.11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.37ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area321.66 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity143 m³·mol⁻¹ChemAxon
Polarizability56.07 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H22O18
IUPAC name(1R,2R)-1-[(14S,15S,19S)-2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-1,3-dihydroxypropan-2-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C27H22O18/c28-4-10(43-25(40)5-1-7(29)15(32)8(30)2-5)17(34)23-24-21(38)14-13(27(42)45-24)12(19(36)22(39)20(14)37)11-6(26(41)44-23)3-9(31)16(33)18(11)35/h1-3,10,17,21,23-24,28-39H,4H2/t10-,17-,21+,23+,24+/m1/s1
InChI KeyTXPZOUVETLGUPE-MEZSAOBOSA-N
Isomeric SMILES[H][C@@]1(O)[C@@H]2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(C=C(O)C(O)=C1O)C(=O)O[C@H]2[C@H](O)[C@@H](CO)OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight634.4528
Monoisotopic Molecular Weight634.0806139
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
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Isochromane
  • 2-benzopyran
  • Benzoate ester
  • Benzopyran
  • Pyrogallol derivative
  • Tricarboxylic acid or derivatives
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14035445
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39200
CRC / DFC (Dictionary of Food Compounds) IDLMM61-V:LMM61-V
EAFUS IDNot Available
Dr. Duke IDPUNICACORTEIN-A
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 IDPunicacortein_A
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Pomegranate3.000 - 3.000 3.000 DUKE
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).