ChemFOnt: Showing chemical card for Ferulic acid 4-glucoside (CFc000281233)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:25 UTC

Chemfont ID

CFc000281233

Molecule Identification

Common Name

Ferulic acid 4-glucoside

Definition

Ferulic 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. Ferulic acid 4-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid 4-glucoside can be found in a number of food items such as redcurrant, gooseberry, highbush blueberry, and blackcurrant, which makes ferulic acid 4-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(3-Methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator
Ferulate 4-glucoside	Generator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid	PhytoBank
(2E)-3-[4-(β-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acid	PhytoBank
(E)-Ferulic acid 4-O-beta-D-glucoside	PhytoBank
(E)-Ferulic acid 4-O-β-D-glucoside	PhytoBank
Ferulic acid 4-O-glucoside	PhytoBank
Ferulic acid 4-O-beta-glucopyranoside	PhytoBank
Ferulic acid 4-O-β-glucopyranoside	PhytoBank
Lavandoside	PhytoBank
trans-4-O-beta-D-Glucopyranosylferulic acid	PhytoBank
trans-4-O-β-D-Glucopyranosylferulic acid	PhytoBank
trans-Ferulic acid 4-beta-D-glucoside	PhytoBank
trans-Ferulic acid 4-β-D-glucoside	PhytoBank
trans-Ferulic acid-4-beta-glucoside	PhytoBank
trans-Ferulic acid-4-β-glucoside	PhytoBank
trans-p-Feruloyl-beta-D-glucopyranoside	PhytoBank
trans-p-Feruloyl-β-D-glucopyranoside	PhytoBank
Ferulic acid 4-O-beta-D-glucopyranoside	PhytoBank
Ferulic acid 4-O-β-D-glucopyranoside	PhytoBank

Chemical Formula

C₁₆H₂₀O₉

Average Molecular Weight

356.3246

Monoisotopic Molecular Weight

356.110732238

IUPAC Name

(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

CAS Registry Number

537-98-4

SMILES

COC1=CC(\C=C\C(O)=O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C16H20O9/c1-23-10-6-8(3-5-12(18)19)2-4-9(10)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-17,20-22H,7H2,1H3,(H,18,19)/b5-3+/t11-,13-,14+,15-,16-/m1/s1

InChI Key

IEMIRSXOYFWPFD-BJGSYIFTSA-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
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Polyol
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301717)

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)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.91 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	-0.59	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.65 m³·mol⁻¹	ChemAxon
Polarizability	34.8 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

HMDB0301717

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000256

KNApSAcK ID

Not Available

Chemspider ID

10212167

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 Ferulic acid 4-glucoside (CFc000281233)

MOL for CFc000281233 (Ferulic acid 4-glucoside)

3D MOL for CFc000281233 (Ferulic acid 4-glucoside)

3D SDF for CFc000281233 (Ferulic acid 4-glucoside)

3D-SDF for CFc000281233 (Ferulic acid 4-glucoside)

PDB for CFc000281233 (Ferulic acid 4-glucoside)

3D PDB for CFc000281233 (Ferulic acid 4-glucoside)

SMILES for CFc000281233 (Ferulic acid 4-glucoside)

INCHI for CFc000281233 (Ferulic acid 4-glucoside)

Structure for CFc000281233 (Ferulic acid 4-glucoside)

3D Structure for CFc000281233 (Ferulic acid 4-glucoside)