Record Information
Version1.0
Creation date2010-04-08 22:07:18 UTC
Update date2015-07-20 22:11:14 UTC
Primary IDFDB006774
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCorilagin
DescriptionCorilagin, also known as corilagin, 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. Corilagin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Corilagin has been detected, but not quantified in, pomegranates. This could make corilagin a potential biomarker for the consumption of these foods.
CAS Number23094-69-1
Structure
Thumb
Synonyms
SynonymSource
(beta-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)ChEBI
1-O-Galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranoseChEBI
(b-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)Generator
(Β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-b-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenate-beta-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenate-β-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-b-D-glucopyranoseGenerator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-β-D-glucopyranoseGenerator
CorillaginHMDB
1-O-Galloyl-3,6-(R)-hexahydroxydiphenol-beta-D-glucoseMeSH
Corillagin HMDB
(β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)Generator
1-O-galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranosemanual
1,3,6-Trigalloyl glucosemanual
Predicted Properties
PropertyValueSource
Water Solubility2.9 g/LALOGPS
logP1.69ALOGPS
logP1.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.41ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area310.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity142.3 m³·mol⁻¹ChemAxon
Polarizability55.34 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H22O18
IUPAC name(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1
InChI KeyTUSDEZXZIZRFGC-XIGLUPEJSA-N
Isomeric SMILESO[C@@H]1[C@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2
Average Molecular Weight634.4528
Monoisotopic Molecular Weight634.0806139
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
  • Macrolide
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Pyrogallol derivative
  • Tricarboxylic acid or derivatives
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kk9-1400901000-f9ee94000466cc2a5d98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0912102000-747eb30db0e36223c7d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910100000-c09c146b163418500f06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-0930000000-7dda7b5a680cd0912f1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-0900214000-ac8138ca0eb7e3474411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900301000-bedf60486b80a8240cc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lfu-4920200000-73686c08722f918b4f00View in MoNA
ChemSpider ID66248
ChEMBL IDCHEMBL449392
KEGG Compound IDC10219
Pubchem Compound ID73568
Pubchem Substance IDNot Available
ChEBI ID3884
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31457
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCORILAGIN
BIGG IDNot Available
KNApSAcK IDC00002915
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCorilagin
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
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lipolyticDUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti radicularDUKE
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
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.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.