Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2020-02-24 19:10:32 UTC
Primary IDFDB002533
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCasuarinin
DescriptionCasuarinin 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. Casuarinin is an extremely weak basic (essentially neutral) compound (based on its pKa). Casuarinin has been detected, but not quantified in, guava. This could make casuarinin a potential biomarker for the consumption of these foods.
CAS Number79786-01-9
Structure
Thumb
Synonyms
SynonymSource
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC41H28O26
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
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
Isomeric 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
Average Molecular Weight936.6454
Monoisotopic Molecular Weight936.086881068
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
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.58%; H 3.01%; O 44.41%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]D +43.6 (c, 1 in MeOH)DFC
Spectroscopic UV Data267 (e 32360) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0609002508-c094b96039e86f5ec15cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0925110507-3197e8fb0b7544359adcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f92-0984100000-926cdce295685ceea662JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0906040518-f1b9253390e762adf299JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0901000311-86b4c88f5c10895df639JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0901000000-1c6442d11a64d5455b58JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10213
Pubchem Compound ID442673
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30632
CRC / DFC (Dictionary of Food Compounds) IDCMH32-T:CMH32-T
EAFUS IDNot Available
Dr. Duke IDCASUARININ
BIGG IDNot Available
KNApSAcK IDC00002910
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti peroxidantDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).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.