ChemFOnt: Showing chemical card for (2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid (CFc000167787)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 00:01:59 UTC

Chemfont ID

CFc000167787

Molecule Identification

Common Name

(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid

Definition

D-glucopyranuronate, also known as glucuronate or glucuronic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. D-glucopyranuronate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-glucopyranuronate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, D-glucopyranuronate has been detected, but not quantified in, several different foods, such as horseradish tree, dandelions, peachs, almonds, and corns. This could make D-glucopyranuronate a potential biomarker for the consumption of these foods. A D-glucopyranuronate in cyclic pyranose form.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-Glucuronic acid	ChEBI
Glucuronate	ChEBI
Glucuronic acid	ChEBI
D-Glucuronate	Generator
D-Glucopyranuronic acid	Generator
Glucuronate, monopotassium	MeSH
Glucuronic acid, monosodium salt	MeSH
Monopotassium glucuronate	MeSH
Glucuronate, monosodium	MeSH
Glucuronic acid, 6-(14)C-labeled, (D)-isomer	MeSH
Glucuronic acid, monopotassium salt	MeSH
Monosodium glucuronate	MeSH

Chemical Formula

C₆H₁₀O₇

Average Molecular Weight

194.1394

Monoisotopic Molecular Weight

194.042652674

IUPAC Name

(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid

Traditional Name

D-glucopyranuronic acid

CAS Registry Number

6556-12-3

SMILES

[H]C1(O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6?/m0/s1

InChI Key

AEMOLEFTQBMNLQ-AQKNRBDQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyran
Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucuronic acid (CHEBI:47952 )
Uronic acids (C00191 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	295 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.79 m³·mol⁻¹	ChemAxon
Polarizability	16.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0187523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006716

KNApSAcK ID

C00001123

Chemspider ID

Not Available

KEGG Compound ID

C00191

BioCyc ID

D-Glucopyranuronate

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94715

PDB ID

Not Available

ChEBI ID

47952

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid (CFc000167787)

MOL for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

3D MOL for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

3D SDF for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

PDB for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

3D PDB for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

SMILES for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

INCHI for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

Structure for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)

3D Structure for CFc000167787 ((2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid)