ChemFOnt: Showing chemical card for Protocatechuic acid 4-glucoside (CFc000283342)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:31 UTC

Chemfont ID

CFc000283342

Molecule Identification

Common Name

Protocatechuic acid 4-glucoside

Definition

Protocatechuic acid 4-glucoside 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. Protocatechuic acid 4-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Protocatechuic acid 4-glucoside can be found in a number of food items such as rosemary, jostaberry, rubus (blackberry, raspberry), and highbush blueberry, which makes protocatechuic acid 4-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
Protocatechuate 4-glucoside	Generator

Chemical Formula

C₁₃H₁₆O₉

Average Molecular Weight

316.262

Monoisotopic Molecular Weight

316.079432095

IUPAC Name

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

Traditional Name

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

CAS Registry Number

99-50-3

SMILES

OCC1OC(OC2=C(O)C=C(C=C2)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-7-2-1-5(12(19)20)3-6(7)15/h1-3,8-11,13-18H,4H2,(H,19,20)

InChI Key

HFFREILXLCWCQH-UHFFFAOYSA-N

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
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303826)

Food

Fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	16.7 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	-1.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.42 m³·mol⁻¹	ChemAxon
Polarizability	29.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303826

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021851

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Protocatechuic acid 4-glucoside (CFc000283342)

MOL for CFc000283342 (Protocatechuic acid 4-glucoside)

3D MOL for CFc000283342 (Protocatechuic acid 4-glucoside)

3D SDF for CFc000283342 (Protocatechuic acid 4-glucoside)

3D-SDF for CFc000283342 (Protocatechuic acid 4-glucoside)

PDB for CFc000283342 (Protocatechuic acid 4-glucoside)

3D PDB for CFc000283342 (Protocatechuic acid 4-glucoside)

SMILES for CFc000283342 (Protocatechuic acid 4-glucoside)

INCHI for CFc000283342 (Protocatechuic acid 4-glucoside)

Structure for CFc000283342 (Protocatechuic acid 4-glucoside)

3D Structure for CFc000283342 (Protocatechuic acid 4-glucoside)