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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-01-22 21:51:40 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005795
Secondary Accession Numbers
  • HMDB05795
Metabolite Identification
Common NamePunicalagin
DescriptionPunicalagin 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 ).
Structure
Data?1582752365
SynonymsNot Available
Chemical FormulaC48H28O30
Average Molecular Weight1084.7179
Monoisotopic Molecular Weight1084.066539556
IUPAC Name3,4,5,15,16,17-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[25.8.0.0²,⁷.0¹⁵,²⁰.0²¹,³⁰.0²⁴,²⁹.0²⁸,³³]pentatriaconta-1(27),2(7),3,5,15,17,19,21(30),22,24(29),28(33),34-dodecaen-10-yl}-9,12-dioxatricyclo[12.4.0.0²,⁷]octadeca-1(18),2,4,6,14,16-hexaene-10-carbaldehyde
Traditional Name3,4,5,15,16,17-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[25.8.0.0²,⁷.0¹⁵,²⁰.0²¹,³⁰.0²⁴,²⁹.0²⁸,³³]pentatriaconta-1(27),2(7),3,5,15,17,19,21(30),22,24(29),28(33),34-dodecaen-10-yl}-9,12-dioxatricyclo[12.4.0.0²,⁷]octadeca-1(18),2,4,6,14,16-hexaene-10-carbaldehyde
CAS Registry Number65995-63-3
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 KeyBFMMRDUWGRKGNX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains).
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassCycloalkanes
Direct ParentCycloalkanes
Alternative ParentsNot Available
Substituents
  • Cycloalkane
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.9 g/LALOGPS
logP3.28ALOGPS
logP3.96ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.12ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area518.78 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity248.25 m³·mol⁻¹ChemAxon
Polarizability94.96 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-329.2330932474
DeepCCS[M+Na]+303.14230932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 10V, Positive-QTOFsplash10-00kr-9000000000-31a2bacc090eaebabe732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 20V, Positive-QTOFsplash10-0ap0-9000000000-08f8a65fd34c2997bbe42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 40V, Positive-QTOFsplash10-00o9-9005004000-4b4dc6989878e43880ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 10V, Negative-QTOFsplash10-001u-9002002000-5a11b760935709b606fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 20V, Negative-QTOFsplash10-0ap0-9001001000-bb39c6a055447f77d5ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 40V, Negative-QTOFsplash10-03dj-8009008000-9a3ab0213eaa1f424e542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 10V, Negative-QTOFsplash10-001r-3009000000-67b4164bc32e06cfad6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 20V, Negative-QTOFsplash10-001r-4009002000-422742771da95ae6466e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 40V, Negative-QTOFsplash10-004j-9004001004-c488d25f16a5188ec6a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 10V, Positive-QTOFsplash10-000i-9000000000-f1ddec289bc93a4b9f3b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 20V, Positive-QTOFsplash10-000l-9001004000-9b664db862f49e1284c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Punicalagin 40V, Positive-QTOFsplash10-004i-9005005003-dcceef8f0e63fc2f26f02021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016425
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPunicalagin
METLIN IDNot Available
PubChem Compound22833653
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chen PS, Li JH: Chemopreventive effect of punicalagin, a novel tannin component isolated from Terminalia catappa, on H-ras-transformed NIH3T3 cells. Toxicol Lett. 2006 May 5;163(1):44-53. Epub 2005 Oct 20. [PubMed:16242868 ]