ChemFOnt: Showing chemical card for Salicylic acid 2-beta-D-glucoside (CFc000282310)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:32 UTC

Chemfont ID

CFc000282310

Molecule Identification

Common Name

Salicylic acid 2-beta-D-glucoside

Definition

Salicylic acid 2-beta-d-glucoside, also known as 2-O-β-glucopyranosylsalicylic acid or sag, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Salicylic acid 2-beta-d-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Salicylic acid 2-beta-d-glucoside can be found in common thyme, rosemary, sweet basil, and sweet marjoram, which makes salicylic acid 2-beta-d-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(beta-D-Glucosyloxy)benzoate	ChEBI
2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}benzoate	ChEBI
Salicylate 2-O-beta-D-glucoside	ChEBI
2-(b-D-Glucosyloxy)benzoate	Generator
2-(b-D-Glucosyloxy)benzoic acid	Generator
2-(beta-D-Glucosyloxy)benzoic acid	Generator
2-(Β-D-glucosyloxy)benzoate	Generator
2-(Β-D-glucosyloxy)benzoic acid	Generator
2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}benzoic acid	Generator
Salicylate 2-O-b-D-glucoside	Generator
Salicylate 2-O-β-D-glucoside	Generator
Salicylic acid 2-O-b-D-glucoside	Generator
Salicylic acid 2-O-beta-D-glucoside	Generator
Salicylic acid 2-O-β-D-glucoside	Generator
2-(b-D-Glucopyranosyloxy)benzoate	Generator
2-(b-D-Glucopyranosyloxy)benzoic acid	Generator
2-(beta-D-Glucopyranosyloxy)benzoic acid	Generator
2-(Β-D-glucopyranosyloxy)benzoate	Generator
2-(Β-D-glucopyranosyloxy)benzoic acid	Generator
Salicylic acid 2-O-β-D-glucoside	MetaCyc
Salicylic acid 2-β-D-glucoside	MetaCyc
2-O-β-glucopyranosylsalicylic acid	MetaCyc
SAG	MetaCyc
2-Hydroxybenzoic acid 2-O-β-D-glucoside	MetaCyc
Salicylate 2-O-β-D-glucoside	Generator
Salicylate 2-b-D-glucoside	Generator
Salicylate 2-beta-D-glucoside	Generator
Salicylate 2-β-D-glucoside	Generator
Salicylic acid 2-b-D-glucoside	Generator
Salicylic acid 2-β-D-glucoside	Generator

Chemical Formula

C₁₃H₁₅O₈

Average Molecular Weight

299.256

Monoisotopic Molecular Weight

299.077241023

IUPAC Name

2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

Traditional Name

2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

CAS Registry Number

None

SMILES

[H][C@]1(CO)O[C@@]([H])(OC2=CC=CC=C2C([O-])=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C13H16O8/c14-5-8-9(15)10(16)11(17)13(21-8)20-7-4-2-1-3-6(7)12(18)19/h1-4,8-11,13-17H,5H2,(H,18,19)/p-1/t8-,9-,10+,11-,13-/m1/s1

InChI Key

TZPBMNKOLMSJPF-BZNQNGANSA-M

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
Hexose monosaccharide
O-glycosyl compound
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Sugar acid
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302794)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	57.6 g/L	ALOGPS
logP	-0.88	ALOGPS
logP	-0.94	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.28 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	2	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

HMDB0302794

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006279

KNApSAcK ID

Not Available

Chemspider ID

5448097

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

145670

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Salicylic acid 2-beta-D-glucoside (CFc000282310)

MOL for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

3D MOL for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

3D SDF for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

3D-SDF for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

PDB for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

3D PDB for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

SMILES for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

INCHI for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

Structure for CFc000282310 (Salicylic acid 2-beta-D-glucoside)

3D Structure for CFc000282310 (Salicylic acid 2-beta-D-glucoside)