ChemFOnt: Showing chemical card for Beta-D-Glucopyranuronic acid (CFc000006322)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:17 UTC

Chemfont ID

CFc000006322

Molecule Identification

Common Name

Beta-D-Glucopyranuronic acid

Definition

Salicylacyl glucuronide 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.

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 Weight

314.2449

Monoisotopic Molecular Weight

314.063782046

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

CAS Registry Number

29315-53-5

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

Functional Ontology

Not Available

Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0010314)

Source

Endogenous

Endogenous (HMDB: HMDB0010314)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Trehalose Degradation I (Low Osmolarity) (PathBank: SMP0122258)

Role

Not Available

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010314

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027466

KNApSAcK ID

Not Available

Chemspider ID

147725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168876

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Beta-D-Glucopyranuronic acid (CFc000006322)

MOL for CFc000006322 (Beta-D-Glucopyranuronic acid)

3D MOL for CFc000006322 (Beta-D-Glucopyranuronic acid)

3D SDF for CFc000006322 (Beta-D-Glucopyranuronic acid)

3D-SDF for CFc000006322 (Beta-D-Glucopyranuronic acid)

PDB for CFc000006322 (Beta-D-Glucopyranuronic acid)

3D PDB for CFc000006322 (Beta-D-Glucopyranuronic acid)

SMILES for CFc000006322 (Beta-D-Glucopyranuronic acid)

INCHI for CFc000006322 (Beta-D-Glucopyranuronic acid)

Structure for CFc000006322 (Beta-D-Glucopyranuronic acid)

3D Structure for CFc000006322 (Beta-D-Glucopyranuronic acid)