ChemFOnt: Showing chemical card for Glucosyringic acid (CFc000282880)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:38 UTC

Chemfont ID

CFc000282880

Molecule Identification

Common Name

Glucosyringic acid

Definition

Glucosyringic acid, also known as glucosyringate, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Glucosyringic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Glucosyringic acid can be found in fennel, which makes glucosyringic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Syringate-4-b-D-glucopyranoside	Generator
Syringate-4-beta-D-glucopyranoside	Generator
Syringate-4-β-D-glucopyranoside	Generator
Syringic acid-4-b-D-glucopyranoside	Generator
Syringic acid-4-β-D-glucopyranoside	Generator
Glucosyringate	Generator

Chemical Formula

C₁₅H₂₀O₁₀

Average Molecular Weight

360.3133

Monoisotopic Molecular Weight

360.10564686

IUPAC Name

3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Traditional Name

3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

CAS Registry Number

33228-65-8

SMILES

COC1=CC(=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)

InChI Key

BLKMDORKRDACEI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Hexose monosaccharide
Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Sugar acid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Polyol
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303364)

Food

Herb and spice

Herb

Fennel (FooDB: FOOD00082)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.1 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.37 m³·mol⁻¹	ChemAxon
Polarizability	34 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

HMDB0303364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012010

KNApSAcK ID

Not Available

Chemspider ID

57487561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14132338

PDB ID

Not Available

ChEBI ID

167538

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glucosyringic acid (CFc000282880)

MOL for CFc000282880 (Glucosyringic acid)

3D MOL for CFc000282880 (Glucosyringic acid)

3D SDF for CFc000282880 (Glucosyringic acid)

3D-SDF for CFc000282880 (Glucosyringic acid)

PDB for CFc000282880 (Glucosyringic acid)

3D PDB for CFc000282880 (Glucosyringic acid)

SMILES for CFc000282880 (Glucosyringic acid)

INCHI for CFc000282880 (Glucosyringic acid)

Structure for CFc000282880 (Glucosyringic acid)

3D Structure for CFc000282880 (Glucosyringic acid)