Casuarinin (CHEM024644)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:50:05 UTC
Update Date2016-11-09 01:17:55 UTC
Accession NumberCHEM024644
Identification
Common NameCasuarinin
ClassSmall Molecule
DescriptionStachyurin is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins 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) 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. Stachyurin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Stachyurin can be found in guava, which makes stachyurin a potential biomarker for the consumption of this food product. Stachyurin is an ellagitannin. It is found in the pericarp of pomegranates (Punica granatum). It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana .
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC41H28O26
Average Molecular Mass936.645 g/mol
Monoisotopic Mass936.087 g/mol
CAS Registry Number79786-01-9
IUPAC Name10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(18),2,4,6,15(19),16-hexaen-11-yl 3,4,5-trihydroxybenzoate
Traditional Name10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(18),2,4,6,15(19),16-hexaen-11-yl 3,4,5-trihydroxybenzoate
SMILESOC1C2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(O)C(O)=C(O)C=C1C(=O)OC2C1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C(=C2)C(=O)OCC1OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI IdentifierInChI=1S/C41H28O26/c42-12-1-7(2-13(43)24(12)48)37(58)64-16-6-63-38(59)11-3-8(22(46)32(56)23(11)47)17-9(4-14(44)25(49)27(17)51)39(60)65-34(16)36-35-31(55)21-20(41(62)66-35)19(29(53)33(57)30(21)54)18-10(40(61)67-36)5-15(45)26(50)28(18)52/h1-5,16,31,34-36,42-57H,6H2
InChI KeyPQTNAAUWLBNDQZ-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Pentacarboxylic acid or derivatives
  • Macrolide
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP2.91ALOGPS
logP3.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.31ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area455.18 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity213.61 m³·mol⁻¹ChemAxon
Polarizability83.49 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0609002508-c094b96039e86f5ec15cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0925110507-3197e8fb0b7544359adcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f92-0984100000-926cdce295685ceea662Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0906040518-f1b9253390e762adf299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0901000311-86b4c88f5c10895df639Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0901000000-1c6442d11a64d5455b58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0600090005-42aad0d4e06d697ce3a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0509020133-0cf474dce6db20af64bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-4609000040-8cf487c944cfd55d6c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000309-c75f7dd0d52fdc26af12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0102000229-5eda92f5e2aadaa7c937Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-2907000051-83cd50007bb4bb614844Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030632
FooDB IDFDB002534
Phenol Explorer IDNot Available
KNApSAcK IDC00002910
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCasuarinin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751061
Kegg Compound IDC10213
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kwon DJ, Bae YS, Ju SM, Goh AR, Choi SY, Park J: Casuarinin suppresses TNF-alpha-induced ICAM-1 expression via blockade of NF-kappaB activation in HaCaT cells. Biochem Biophys Res Commun. 2011 Jun 17;409(4):780-5. doi: 10.1016/j.bbrc.2011.05.088. Epub 2011 May 20.
2. Kuo PL, Hsu YL, Lin TC, Lin LT, Chang JK, Lin CC: Casuarinin from the bark of Terminalia arjuna induces apoptosis and cell cycle arrest in human breast adenocarcinoma MCF-7 cells. Planta Med. 2005 Mar;71(3):237-43.
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.