ChemFOnt: Showing chemical card for 1-O-Feruloyl-beta-D-glucopyranose (CFc000281608)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:10 UTC

Chemfont ID

CFc000281608

Molecule Identification

Common Name

1-O-Feruloyl-beta-D-glucopyranose

Definition

1-o-feruloyl-beta-d-glucopyranose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1-o-feruloyl-beta-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-feruloyl-beta-d-glucopyranose can be found in loquat, which makes 1-o-feruloyl-beta-d-glucopyranose a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid	Generator
1-O-Feruloyl-b-D-glucopyranose	Generator
1-O-Feruloyl-β-D-glucopyranose	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-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Traditional Name

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

CAS Registry Number

205254-22-4

SMILES

COC1=CC=C(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1O

InChI Identifier

InChI=1S/C16H20O9/c1-23-10-4-2-8(6-9(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

RFTKPXQZIVKVOP-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
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Oxane
Monosaccharide
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302092)

Food

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.96 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.82	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	35.22 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

HMDB0302092

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001848

KNApSAcK ID

Not Available

Chemspider ID

59696281

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 1-O-Feruloyl-beta-D-glucopyranose (CFc000281608)

MOL for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

3D MOL for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

3D SDF for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

3D-SDF for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

PDB for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

3D PDB for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

SMILES for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

INCHI for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

Structure for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)

3D Structure for CFc000281608 (1-O-Feruloyl-beta-D-glucopyranose)