Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:04 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030632
Secondary Accession Numbers
  • HMDB30632
Metabolite Identification
Common 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). Outside of the human body, casuarinin has been detected, but not quantified in, guava. This could make casuarinin a potential biomarker for the consumption of these foods. After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana. It is a highly active carbonic anhydrase inhibitor. Casuarinin is an ellagitannin. It is an isomer of casuarictin.
Structure
Data?1563862015
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 Weight936.6454
Monoisotopic Molecular Weight936.086881068
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
CAS Registry Number79786-01-9
SMILES
OC1C2OC(=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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 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
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+H]+275.23630932474
DeepCCS[M-H]-273.51330932474
DeepCCS[M-2H]-307.7130932474
DeepCCS[M+Na]+281.50830932474
AllCCS[M+H]+275.232859911
AllCCS[M+H-H2O]+275.432859911
AllCCS[M+NH4]+275.032859911
AllCCS[M+Na]+274.932859911
AllCCS[M-H]-286.432859911
AllCCS[M+Na-2H]-290.432859911
AllCCS[M+HCOO]-294.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 10V, Positive-QTOFsplash10-0gbi-0609002508-c094b96039e86f5ec15c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 20V, Positive-QTOFsplash10-0uxr-0925110507-3197e8fb0b7544359adc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 40V, Positive-QTOFsplash10-0f92-0984100000-926cdce295685ceea6622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 10V, Negative-QTOFsplash10-00kr-0906040518-f1b9253390e762adf2992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 20V, Negative-QTOFsplash10-014i-0901000311-86b4c88f5c10895df6392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 40V, Negative-QTOFsplash10-00or-0901000000-1c6442d11a64d5455b582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 10V, Negative-QTOFsplash10-000i-0600090005-42aad0d4e06d697ce3a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 20V, Negative-QTOFsplash10-004i-0509020133-0cf474dce6db20af64bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 40V, Negative-QTOFsplash10-002e-4609000040-8cf487c944cfd55d6c4e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 10V, Positive-QTOFsplash10-000i-0000000309-c75f7dd0d52fdc26af122021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 20V, Positive-QTOFsplash10-000i-0102000229-5eda92f5e2aadaa7c9372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Casuarinin 40V, Positive-QTOFsplash10-0udl-2907000051-83cd50007bb4bb6148442021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002534
KNApSAcK IDC00002910
Chemspider IDNot Available
KEGG Compound IDC10213
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCasuarinin
METLIN IDNot Available
PubChem Compound131751061
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. 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. [PubMed:21621513 ]
  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. [PubMed:15770544 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Casuarinin → Castanindetails