ChemFOnt: Showing chemical card for trans-p-Feruloyl-beta-D-glucopyranoside (CFc000281468)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:53 UTC

Chemfont ID

CFc000281468

Molecule Identification

Common Name

trans-p-Feruloyl-beta-D-glucopyranoside

Definition

Trans-p-feruloyl-beta-d-glucopyranoside, also known as 1-feruloyl-D-glucose, is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. Trans-p-feruloyl-beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-p-feruloyl-beta-d-glucopyranoside can be found in a number of food items such as green bell pepper, pepper (c. annuum), yellow bell pepper, and orange bell pepper, which makes trans-p-feruloyl-beta-d-glucopyranoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-1-O-Feruloyl-beta-D-glucopyranose	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamoyl-beta-D-glucopyranose	ChEBI
1-Feruloyl-D-glucose	ChEBI
1-O-(e)-Feruloyl-beta-D-glucose	ChEBI
1-O-(e)-p-Feruloyl-beta-D-glucopyranose	ChEBI
1-O-[(e)-Feruloyl]-beta-D-glucose	ChEBI
1-O-trans-Feruloyl-beta-D-glucopyranoside	ChEBI
Ferulic acid beta-D-glucopyranosyl ester	ChEBI
trans-p-Feruloyl-beta-D-glucopyranoside	ChEBI
(e)-1-O-Feruloyl-b-D-glucopyranose	Generator
(e)-1-O-Feruloyl-β-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-b-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose	Generator
1-O-(e)-Feruloyl-b-D-glucose	Generator
1-O-(e)-Feruloyl-β-D-glucose	Generator
1-O-(e)-p-Feruloyl-b-D-glucopyranose	Generator
1-O-(e)-p-Feruloyl-β-D-glucopyranose	Generator
1-O-[(e)-Feruloyl]-b-D-glucose	Generator
1-O-[(e)-Feruloyl]-β-D-glucose	Generator
1-O-trans-Feruloyl-b-D-glucopyranoside	Generator
1-O-trans-Feruloyl-β-D-glucopyranoside	Generator
Ferulate b-D-glucopyranosyl ester	Generator
Ferulate beta-D-glucopyranosyl ester	Generator
Ferulate β-D-glucopyranosyl ester	Generator
Ferulic acid b-D-glucopyranosyl ester	Generator
Ferulic acid β-D-glucopyranosyl ester	Generator
trans-p-Feruloyl-b-D-glucopyranoside	Generator
trans-p-Feruloyl-β-D-glucopyranoside	Generator
1-O-Feruloyl-b-D-glucose	Generator
1-O-Feruloyl-β-D-glucose	Generator
1-O-(trans-Feruloyl)-beta-D-glucose	ChEBI
1-O-(trans-Feruloyl)-b-D-glucose	Generator
1-O-(trans-Feruloyl)-β-D-glucose	Generator

Chemical Formula

C₁₆H₂₀O₉

Average Molecular Weight

356.3246

Monoisotopic Molecular Weight

356.110732238

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

117405-51-3

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1

InChI Identifier

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

InChI Key

JWRQVQWBNRGGPK-PMQCXRHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:81321 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301952)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Tea

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.98 g/L	ALOGPS
logP	-0.44	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.94 m³·mol⁻¹	ChemAxon
Polarizability	34.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301952

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001666

KNApSAcK ID

Not Available

Chemspider ID

26336946

KEGG Compound ID

C17759

BioCyc ID

CPD-15281

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

81321

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for trans-p-Feruloyl-beta-D-glucopyranoside (CFc000281468)

MOL for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D MOL for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D SDF for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D-SDF for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

PDB for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D PDB for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

SMILES for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

INCHI for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

Structure for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D Structure for CFc000281468 (trans-p-Feruloyl-beta-D-glucopyranoside)