ContaminantDB: Epicatechin 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 01:35:06 UTC

Update Date

2016-11-09 01:22:30 UTC

Accession Number

CHEM041598

Identification

Common Name

Epicatechin 3'-glucuronide

Class

Small Molecule

Description

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

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Epicatechin 3'-O-glucuronide	HMDB
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylate	HMDB

Chemical Formula

C₂₁H₂₂O₁₂

Average Molecular Mass

466.392 g/mol

Monoisotopic Mass

466.111 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylic acid

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=C1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C21H22O12/c22-8-4-11(24)9-6-12(25)18(31-13(9)5-8)7-1-2-10(23)14(3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15+,16+,17-,18-,19+,21-/m1/s1

InChI Key

BUONZQIZWIITTB-CVPXIJHMSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Substituents

Flavonoid-3p-o-glucuronide
Catechin
Hydroxyflavonoid
Flavan-3-ol
3-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Chromane
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Phenol
Pyran
Benzenoid
Monosaccharide
Oxane
Monocyclic benzene moiety
Hydroxy acid
Secondary alcohol
Acetal
Polyol
Ether
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	2.89 g/L	ALOGPS
logP	0.08	ALOGPS
logP	-0.15	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.01 m³·mol⁻¹	ChemAxon
Polarizability	42.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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	splash10-054k-9108500000-11fc73b483920ad69445	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-7200029000-8ed5a427129980dfbe90	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 (TMS_5_30) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_19) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_23) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("(-)-Epicatechin 3'-O-glucuronide,5TMS,#30" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00rg-0690800000-1545d8c57f3e28f4a41e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007c-0970100000-467fb1b9e89f4d4e2654	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0910000000-d139ac043424be2eebb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-1340900000-f16fa20f169f9fd80f39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2891400000-d53ae30092c98483fff9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-2930000000-3421cc335bec124835c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0040900000-865fa171ff6eba7feaf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2291100000-e08eaada0e748a6c60ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-5594000000-4e8b5e9d3e350a32525d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kg-0080900000-4bdd5c9903d79867c7b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-0495600000-f6384e044df1a396ea7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-1891000000-3211d88eb1036587af91	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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

HMDB0041728

FooDB ID

FDB029894

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

30777621

ChEBI ID

149599

PubChem Compound ID

76969982

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.

Epicatechin 3'-glucuronide (CHEM041598)

Structure for CHEM041598: Epicatechin 3'-glucuronide