ContaminantDB: 5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 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 01:34:18 UTC

Update Date

2016-11-09 01:22:30 UTC

Accession Number

CHEM041562

Identification

Common Name

5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-glucuronide

Class

Small Molecule

Description

5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 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
5-(3',5'-Dihydroxyphenyl)-g-valerolactone 3-O-glucuronide	Generator
5-(3',5'-Dihydroxyphenyl)-γ-valerolactone 3-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylate	HMDB
5-(3',5'-Dihydroxyphenyl)-g-valerolactone 3-glucuronide	HMDB
5-(3',5'-Dihydroxyphenyl)-γ-valerolactone 3-glucuronide	HMDB

Chemical Formula

C₁₇H₂₀O₁₀

Average Molecular Mass

384.335 g/mol

Monoisotopic Mass

384.106 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

SMILES

O[C@@H]1[C@@H](O)[C@H](OC2=CC(O)=CC(CC3CCC(=O)O3)=C2)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C17H20O10/c18-8-3-7(4-9-1-2-11(19)25-9)5-10(6-8)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h3,5-6,9,12-15,17-18,20-22H,1-2,4H2,(H,23,24)/t9?,12-,13-,14+,15-,17+/m0/s1

InChI Key

RUSMDDXSDLDLKU-PHPHFFAHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Tetrahydrofuran
Lactone
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	6.91 g/L	ALOGPS
logP	-0.26	ALOGPS
logP	-0.33	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.32 m³·mol⁻¹	ChemAxon
Polarizability	35.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	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	splash10-07vs-7393000000-9e5d2516c1bfcf90a3a4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-3022029000-4fb28db4992e513764ac	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 (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap0-0449000000-5139e0a7c2df22349522	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-0931000000-a4004bfe97b134711408	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059e-1910000000-7c6816701e1c3ff504d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0540-1339000000-318726d27da0c33c62a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3795000000-1307b07d619b8baedc2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-8930000000-931db6da95b7bf8a978a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05o0-0239000000-7c65704b4b9e8f33f4b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-6793000000-3e14f71356901c28cab5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2910000000-f49273419e127ee75359	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0249000000-62eab577644c14d2d54a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0699-0549000000-5b06ea36602ad433dfaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar0-2931000000-c85dd8dcf56ecae9b078	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
1D NMR	1H 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

HMDB0041693

FooDB ID

FDB029857

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

35015220

ChEBI ID

88659

PubChem Compound ID

124202085

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.

5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-glucuronide (CHEM041562)

Structure for CHEM041562: 5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-glucuronide