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Human Metabolome Database Version 3.5

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Showing metabocard for Punicalagin (HMDB05795)

Record Information
Version 3.5
Creation Date 2007-01-22 14:51:40 -0700
Update Date 2013-02-08 17:14:19 -0700
HMDB ID HMDB05795
Secondary Accession Numbers None
Metabolite Identification
Common Name Punicalagin
Description Punicalagin is the major tannin component of Terminalia catappa and have been characterized to possess antioxidative and anti-genotoxic activities. T. catappa has been a popular folk medicine for preventing hepatoma and treating hepatitis in Taiwan; the leaves contain many hydrolyzable tannins. Although the leaves of T. catappa have been claimed to be effective in preventing hepatoma, the mechanism of its chemopreventive effect remains to be elucidated, and their effects on reactive oxygen species (ROS) mediated carcinogenesis are still unclear. (PMID: 16242868 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
    Chemical Formula C48H28O30
    Average Molecular Weight 1084.7179
    Monoisotopic Molecular Weight 1084.066539556
    IUPAC Name 3,4,5,15,16,17-hexahydroxy-8,13-dioxo-11-{3,4,5,11,17,18,19,22,23,34,35-undecahydroxy-8,14,26,31-tetraoxo-9,13,25,32-tetraoxaheptacyclo[25.8.0.0^{2,7}.0^{15,20}.0^{21,30}.0^{24,29}.0^{28,33}]pentatriaconta-1(27),2(7),3,5,15,17,19,21,23,28(33),29,34-dodecaen-10-yl}-9,12-dioxatricyclo[12.4.0.0^{2,7}]octadeca-1(18),2,4,6,14,16-hexaene-10-carbaldehyde
    Traditional IUPAC Name 3,4,5,15,16,17-hexahydroxy-8,13-dioxo-11-{3,4,5,11,17,18,19,22,23,34,35-undecahydroxy-8,14,26,31-tetraoxo-9,13,25,32-tetraoxaheptacyclo[25.8.0.0^{2,7}.0^{15,20}.0^{21,30}.0^{24,29}.0^{28,33}]pentatriaconta-1(27),2(7),3,5,15,17,19,21,23,28(33),29,34-dodeca
    CAS Registry Number 65995-63-3
    SMILES OC1COC(=O)C2=CC(O)=C(O)C(O)=C2C2=C3C(=O)OC4=C5C(C(=O)OC(C(O)=C2O)=C35)=C(C(O)=C4O)C2=C(C=C(O)C(O)=C2O)C(=O)OC1C1OC(=O)C2=C(O)C(O)=C(O)C=C2C2=C(O)C(O)=C(O)C=C2C(=O)OC1C=O
    InChI Identifier InChI=1S/C48H28O30/c49-5-16-40(76-46(70)20-7(1-11(50)30(58)34(20)62)17-8(44(68)74-16)2-12(51)27(55)31(17)59)39-15(54)6-73-43(67)9-3-13(52)28(56)32(60)18(9)21-25-23-24-26(48(72)78-41(23)37(65)35(21)63)22(36(64)38(66)42(24)77-47(25)71)19-10(45(69)75-39)4-14(53)29(57)33(19)61/h1-5,15-16,39-40,50-66H,6H2
    InChI Key BFMMRDUWGRKGNX-UHFFFAOYSA-N
    Chemical Taxonomy
    Kingdom Organic Compounds
    Super Class Tannins
    Class Hydrolyzable Tannins
    Sub Class N/A
    Other Descriptors
    • Aromatic Heteropolycyclic Compounds
    Substituents
    • 1,2 Diphenol
    • Benzopyran
    • Carboxylic Acid Ester
    • Coumarin
    • Gallic Acid Derivative
    • Hemiacetal
    • Hydroxybenzoic Acid
    • Isocoumarin
    • Lactone
    • Oxane
    • Phenol
    • Phenol Derivative
    • Pyran
    • Pyranone
    • Pyrogallol Derivative
    • Resorcinol
    Direct Parent Hydrolyzable Tannins
    Ontology
    Status Expected and Not Quantified
    Origin
    • Plant
    • Drug
    Biofunction Not Available
    Application Not Available
    Cellular locations Not Available
    Physical Properties
    State Solid
    Experimental Properties
    Property Value Reference
    Melting Point Not Available Not Available
    Boiling Point Not Available Not Available
    Water Solubility Not Available Not Available
    LogP Not Available Not Available
    Predicted Properties
    Property Value Source
    Water Solubility 1.9 g/L ALOGPS
    LogP 3.28 ALOGPS
    LogP 3.96 ChemAxon
    LogS -2.76 ALOGPS
    pKa (strongest acidic) 5.12 ChemAxon
    pKa (strongest basic) -4.4 ChemAxon
    Hydrogen Acceptor Count 24 ChemAxon
    Hydrogen Donor Count 17 ChemAxon
    Polar Surface Area 518.78 A2 ChemAxon
    Rotatable Bond Count 2 ChemAxon
    Refractivity 248.25 ChemAxon
    Polarizability 94.96 ChemAxon
    Formal Charge 0 ChemAxon
    Physiological Charge -2 ChemAxon
    Spectra
    Not Available
    Biological Properties
    Cellular Locations Not Available
    Biofluid Locations Not Available
    Tissue Location Not Available
    Pathways Not Available
    Normal Concentrations
    Not Available
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease References None
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID 449 Link_out
    FoodDB ID FDB016425
    KNApSAcK ID C00035378 Link_out
    Chemspider ID 17216347 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Punicalagin Link_out
    NuGOwiki Link HMDB05795 Link_out
    Metagene Link HMDB05795 Link_out
    METLIN ID Not Available
    PubChem Compound 22833653 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References Not Available