ContaminantDB: Epigallocatechin 3-glucuronide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-27 01:33:03 UTC

Update Date

2016-11-09 01:22:29 UTC

Accession Number

CHEM041506

Identification

Common Name

Epigallocatechin 3-glucuronide

Class

Small Molecule

Description

(-)-Epigallocatechin 3-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Epigallocatechin 3-O-glucuronide	HMDB
(2S,3S,4S,5R,6R)-6-{[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₂₁H₂₂O₁₃

Average Molecular Mass

482.392 g/mol

Monoisotopic Mass

482.106 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

SMILES

O[C@@H]1[C@@H](O)[C@H](O[C@@H]2CC3=C(O[C@@H]2C2=CC(O)=C(O)C(O)=C2)C=C(O)C=C3O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C21H22O13/c22-7-3-9(23)8-5-13(33-21-17(29)15(27)16(28)19(34-21)20(30)31)18(32-12(8)4-7)6-1-10(24)14(26)11(25)2-6/h1-4,13,15-19,21-29H,5H2,(H,30,31)/t13-,15+,16+,17-,18-,19+,21-/m1/s1

InChI Key

ZTOAOZDTXSRHIB-BBGDWMAASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Pyran
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Acetal
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.7 g/L	ALOGPS
logP	1.05	ALOGPS
logP	0.041	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	226.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.26 m³·mol⁻¹	ChemAxon
Polarizability	43.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-9106300000-552f6ab3cff61b7abb97	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001i-3372129000-3f8dcfea2d221f87f6ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_19) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_31) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_39) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_40) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_23) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_24) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_44) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_50) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("(-)-Epigallocatechin 3-glucuronide,3TMS,#19" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0914600000-c39b886d397274aa8aab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059i-0922000000-4de1b6b85fd8744dc69f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-1900000000-4cf9036d71c53dacf819	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-1304900000-446f5d442ea29d91a350	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2729500000-01d07573e50e75351131	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-3913000000-25aa7776faf06e9d1e6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-0001900000-4f187db62e9c12f91263	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-8519600000-3fb6ec1f08f8cce621d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052u-8569300000-38b7259de1fc36026007	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0001900000-5397aa7c48e51423d07f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-0103900000-34b3c6d2aada810dff16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0670-1922200000-23a0641628e7027c7e8c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041639

FooDB ID

FDB029794

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

30777584

ChEBI ID

168759

PubChem Compound ID

101449862

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.

Epigallocatechin 3-glucuronide (CHEM041506)

Structure for CHEM041506: Epigallocatechin 3-glucuronide