ContaminantDB: beta-D-Glucopyranuronic acid

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

Record Information

Version

1.0

Creation Date

2016-05-26 18:00:31 UTC

Update Date

2016-11-09 01:22:06 UTC

Accession Number

CHEM039581

Identification

Common Name

beta-D-Glucopyranuronic acid

Class

Small Molecule

Description

Beta-D-Glucopyranuronic acid is a natural human metabolite of acetylsilacylic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
b-D-Glucopyranuronate	Generator
b-D-Glucopyranuronic acid	Generator
beta-D-Glucopyranuronate	Generator
Β-D-glucopyranuronate	Generator
Β-D-glucopyranuronic acid	Generator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(2-hydroxybenzoyl)oxyoxane-2-carboxylic acid	HMDB
1-(2-Hydroxybenzoate	HMDB
1-(2-Hydroxybenzoate) beta-D-glucopyranuronic acid	HMDB
1-(2-Hydroxybenzoate) beta-delta-glucopyranuronic acid	HMDB
1-(2-Hydroxybenzoic acid	HMDB
Acyl sa glucuronide	HMDB
Salicyl acyl glucuronide	HMDB
Salicylacyl glucuronide	HMDB

Chemical Formula

C₁₃H₁₄O₉

Average Molecular Mass

314.245 g/mol

Monoisotopic Mass

314.064 g/mol

CAS Registry Number

29315-53-5

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxybenzoyloxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxybenzoyloxy)oxane-2-carboxylic acid

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=CC=C2O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C13H14O9/c14-6-4-2-1-3-5(6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19)/t7-,8-,9+,10-,13-/m0/s1

InChI Key

IXVVXKRKCLJCKA-UNLLLRGISA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Pyran
Hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Oxane
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
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	20.8 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	0.23	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.59 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	2	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	splash10-0a4i-9430000000-2a4f0c4deaff6c4abb73	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-06r6-2511119000-59f9672d4beab9a8844f	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	splash10-007a-0921000000-deba0e5c59d184c9d5e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0900000000-bbf3cfca43ba05860073	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-0c1d8f8007fa6b2a3c2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-029i-2933000000-5b35c7a1e0ad8e165c2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-7920000000-b2e496121f275b5584ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-0e8d009e9ee72ff94b65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ox-4922000000-acce7bb9f6e3f0a62380	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9700000000-1f4af5f176d9b59ee9fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f0d349229272c9b8a05a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-1914000000-4de49b2233eaa00d2452	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1931000000-366fb65d354fc06e6d41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g4l-9600000000-054bb7d4dc56cf6bd12e	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

HMDB0010314

FooDB ID

FDB027466

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

147725

ChEBI ID

Not Available

PubChem Compound ID

168876

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70.

2. Dickinson RG, Baker PV, King AR: Studies on the reactivity of acyl glucuronides--VII. Salicyl acyl glucuronide reactivity in vitro and covalent binding of salicylic acid to plasma protein of humans taking aspirin. Biochem Pharmacol. 1994 Feb 9;47(3):469-76.

3. Shen JJ, Wanwimolruk S, Roberts MS: Novel direct high-performance liquid chromatographic method for determination of salicylate glucuronide conjugates in human urine. J Chromatogr. 1991 Apr 19;565(1-2):309-20.

4. Patel DK, Notarianni LJ, Bennett PN: Comparative metabolism of high doses of aspirin in man and rat. Xenobiotica. 1990 Aug;20(8):847-54.

5. Day RO, Furst DE, Dromgoole SH, Paulus HE: Changes in salicylate serum concentration and metabolism during chronic dosing in normal volunteers. Biopharm Drug Dispos. 1988 May-Jun;9(3):273-83.

beta-D-Glucopyranuronic acid (CHEM039581)

Structure for CHEM039581: beta-D-Glucopyranuronic acid