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Showing Compound Casuarictin (FDB018815)

Record Information
Version1.0
Creation date2010-04-08 22:13:57 UTC
Update date2025-11-19 02:15:02 UTC
Primary IDFDB018815
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCasuarictin
DescriptionCasuarictin 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. Casuarictin is an extremely weak basic (essentially neutral) compound (based on its pKa). Casuarictin has been detected, but not quantified in, several different foods, such as acorns, cloves, guava, nuts, and rubus (blackberry, raspberry). This could make casuarictin a potential biomarker for the consumption of these foods.
CAS Number79786-00-8
Structure
Thumb
MOLSDFPDBSMILESInChI
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
  • 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
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 IDCHEMBL446979
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 IDCasuarictin
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 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.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.