Record Information
Version1.0
Creation date2010-04-08 22:13:57 UTC
Update date2018-05-29 01:38:51 UTC
Primary IDFDB018815
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCasuarictin
DescriptionIsolated from Corylus heterophylla (Siberian filbert). Casuarictin is found in many foods, some of which are nuts, cloves, acorn, and guava.
CAS Number79786-00-8
Structure
Thumb
Synonyms
SynonymSource
1(Beta)-O-GalloylpedunculaginChEMBL
1(b)-O-GalloylpedunculaginGenerator
1(β)-O-galloylpedunculaginGenerator
Casuarictin, (alpha-D-GLC)-stereoisomerMeSH
Casuarictin, (beta-D-GLC)-isomerMeSH
Casuarictin, beta-D-GLC)-(2(R),3(R)-isomerMeSH
1-O-Galloyl-2,3;4,6-bis-(S)-hexahydroxydiphenoyl-b-D-glucopyranosedb_source
Casuarictindb_source
Predicted Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP3.22ALOGPS
logP3.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7.25ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area444.18 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity212.9 m³·mol⁻¹ChemAxon
Polarizability83.77 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC41H28O26
IUPAC name(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1
InChI KeySWRFKGRMQVLMKA-JIZJWZDPSA-N
Isomeric SMILESOC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]2[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]12
Average Molecular Weight936.6454
Monoisotopic Molecular Weight936.086881068
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassTannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Pentacarboxylic acid or derivatives
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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]20D +35 (c, 0.2 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID398349
ChEMBL IDNot Available
KEGG Compound IDC10212
Pubchem Compound ID452242
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39244
CRC / DFC (Dictionary of Food Compounds) IDLMT21-S:LMT25-W
EAFUS IDNot Available
Dr. Duke IDCASUARICTIN
BIGG IDNot Available
KNApSAcK IDC00002909
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 hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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.