Record Information
Version1.0
Creation date2010-04-08 22:14:02 UTC
Update date2019-11-26 03:16:54 UTC
Primary IDFDB018931
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCastalagin
DescriptionCastalagin 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. Castalagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Castalagin has been detected, but not quantified in, a few different foods, such as european chestnuts, nuts, and pomegranates. This could make castalagin a potential biomarker for the consumption of these foods.
CAS Number36001-47-5
Structure
Thumb
Synonyms
SynonymSource
Vescalagin, (33beta)-isomerMeSH
VescaleneMeSH
VescalaginMeSH
VescalinMeSH
Castalagindb_source
Predicted Properties
PropertyValueSource
Water Solubility5.79 g/LALOGPS
logP2.74ALOGPS
logP2.03ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.14ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area455.18 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity212.69 m³·mol⁻¹ChemAxon
Polarizability81.36 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC41H26O26
IUPAC name(1R,2R,20R,42S,46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1^{38,42}.0^{2,20}.0^{5,10}.0^{11,16}.0^{23,28}.0^{33,45}.0^{34,39}]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone
InChI IdentifierInChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11-,31-,34-,35+,36+/m1/s1
InChI KeyUDYKDZHZAKSYCO-JLQXGYSZSA-N
Isomeric SMILESO[C@H]1[C@@H]2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(O)C(O)=C(O)C3=C1C(=O)O[C@H]2[C@@H]1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C=C2C(=O)OC[C@H]1OC(=O)C1=C3C(O)=C(O)C(O)=C1
Average Molecular Weight934.6295
Monoisotopic Molecular Weight934.071231004
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
  • Gallic acid or derivatives
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.69%; H 2.80%; O 44.51%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]26D -99.9 (c, 0.52 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID147097
ChEMBL IDCHEMBL607711
KEGG Compound IDNot Available
Pubchem Compound ID168165
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30602
CRC / DFC (Dictionary of Food Compounds) IDLNJ53-M:LNH45-B
EAFUS IDNot Available
Dr. Duke IDCASTALAGIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCastalagin
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
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Shuaibu MN, Pandey K, Wuyep PA, Yanagi T, Hirayama K, Ichinose A, et al. Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro. Parasitol Res. 2008 Nov;103(6):1333–8. Pubmed [Structure]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).