Showing Compound Corilagin (FDB006774)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:18 UTC

Update date

2019-11-26 03:01:17 UTC

Primary ID

FDB006774

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Corilagin

Description

Corilagin, also known as gallotannin, 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 has been detected, but not quantified in, pomegranates (Punica granatum). This could make corilagin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Corilagin.

CAS Number

23094-69-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(beta-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)	ChEBI
1-O-Galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranose	ChEBI
(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-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-beta-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-β-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-b-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-β-D-glucopyranose	Generator
1-O-Galloyl-3,6-(R)-hexahydroxydiphenol-beta-D-glucose	MeSH
Corillagin	HMDB
(β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)	Generator
1-O-galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranose	manual
1,3,6-Trigalloyl glucose	manual

Predicted Properties

Property	Value	Source
Water Solubility	2.9 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.41	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	310.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.3 m³·mol⁻¹	ChemAxon
Polarizability	55.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C27H22O18

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 Identifier

InChI=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 Key

TUSDEZXZIZRFGC-XIGLUPEJSA-N

Isomeric SMILES

O[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 Weight

634.4528

Monoisotopic Molecular Weight

634.0806139

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

gallate ester (CHEBI:3884 )
ellagitannin (CHEBI:3884 )
Ellagitannins (C10219 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Corilagin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kk9-1400901000-f9ee94000466cc2a5d98	Spectrum
Predicted GC-MS	Corilagin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Corilagin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0912102000-747eb30db0e36223c7d1	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0910100000-c09c146b163418500f06	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fi0-0930000000-7dda7b5a680cd0912f1b	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gc0-0900214000-ac8138ca0eb7e3474411	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900301000-bedf60486b80a8240cc1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0lfu-4920200000-73686c08722f918b4f00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0400709000-974c3fccc24061e5bfcb	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gbi-1900801000-39727df01a08af3c68c2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3900420000-d3d45ea63d8935f0bd13	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-0900101000-19cd1c40012f2b1310f3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0i29-0900522000-f1a8081561856ad5378d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0100-5900750000-0bf5a21943a40e85788b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

3884

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31457

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CORILAGIN

BIGG ID

Not Available

KNApSAcK ID

C00002915

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Corilagin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lipolytic			DUKE
anti mutagenic			DUKE
antioxidant	22586	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 peroxidant			DUKE
anti radicular			DUKE
topoisomerase-II inhibitor	50750	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 inhibitor	50276	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 inhibitor	35634	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