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Showing Compound Punicalin (FDB018735)

Record Information
Version1.0
Creation date2010-04-08 22:13:54 UTC
Update date2025-11-19 02:14:10 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
MOLSDFPDBSMILESInChI
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
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-d43238e73ab3521907282019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ldr-0000000900-542c5f8d98f3346a460c2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0py0-0000003900-f4c1052f02a4c9cfdbf22019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0000002900-18dfaf19efa50dec18b32019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gwr-2000000900-ef40b5feb7b3c9a6ed992019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h0s-1000009300-95432b30828166824ab22019-02-23View Spectrum
NMRNot Available
ChemSpider ID28428695
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 An agent that combats HIV infection, playing a crucial biological role in blocking viral replication. Therapeutically, it's used to manage and treat HIV/AIDS, preventing disease progression. Key medical uses include suppressing viral loads, boosting immune systems, and reducing the risk of opportunistic infections and AIDS-related complications.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
HIV-reverse-transcriptase inhibitor23924 An agent that blocks the activity of reverse transcriptase, an enzyme essential for HIV replication, reducing viral load and slowing disease progression. Therapeutically, it is used to treat HIV/AIDS, often in combination with other antiretroviral medications to prevent drug resistance and manage symptoms.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.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.