ChemFOnt: Showing chemical card for 3-O-Feruloylquinic acid (CFc000220674)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:56 UTC

Chemfont ID

CFc000220674

Molecule Identification

Common Name

3-O-Feruloylquinic acid

Definition

5-Feruloylquinic acid, also known as 5-feruloylquinate or 5-FQA, 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. 5-Feruloylquinic acid is found, on average, in the highest concentration within a few different foods, such as robusta coffees (Coffea canephora), coffees (Coffea), and arabica coffees (Coffea arabica) and in a lower concentration in carrots (Daucus carota ssp. sativus), rubus (blackberry, raspberry), and gooseberries (Ribes uva-crispa). 5-Feruloylquinic acid has also been detected, but not quantified in, several different foods, such as pears (Pyrus communis), strawberries (Fragaria X ananassa), corns (Zea mays), apples (Malus pumila), and highbush blueberries (Vaccinium corymbosum). This could make 5-feruloylquinic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Feruloylquinic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Feruloylquinate	Generator
5-FQA	HMDB
5-Ferulylquinic acid	HMDB
5-O-(e)-Feruloylquinic acid	HMDB
5-O-Feruloylquinic acid	HMDB
Feruloylquinic acid	HMDB
trans-5-O-Feruloyl quinic acid	HMDB
trans-5-O-Feruloylquinic acid	HMDB
5-Feruloylquinic acid	HMDB

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.3353

Monoisotopic Molecular Weight

368.110732238

IUPAC Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

62929-69-5

SMILES

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

InChI Identifier

InChI=1S/C17H20O9/c1-25-12-6-9(2-4-10(12)18)3-5-14(20)26-13-8-17(24,16(22)23)7-11(19)15(13)21/h2-6,11,13,15,18-19,21,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,13-,15+,17-/m1/s1

InChI Key

RAGZUCNPTLULOL-KQJPBSFVSA-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
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Phenoxy compound
Phenol ether
Beta-hydroxy acid
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0240411)
Extracellular (HMDB: HMDB0240411)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0240411)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0240411)

Source

Endogenous

Endogenous (HMDB: HMDB0240411)

Plant

Plant (HMDB: HMDB0240411)
Coffea (HMDB: HMDB0240411)

Exogenous

Food

Food (HMDB: HMDB0240411)

Vegetable

Root vegetable

Chicory (FooDB: FOOD00049)

Fruit vegetable

Garden tomato (FooDB: FOOD00171)
Garden tomato (var.) (FooDB: FOOD00173)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.04 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.12	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.72 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

HMDB0240478

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000249

KNApSAcK ID

C00052735

Chemspider ID

8309124

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 3-O-Feruloylquinic acid (CFc000220674)

MOL for CFc000220674 (3-O-Feruloylquinic acid)

3D MOL for CFc000220674 (3-O-Feruloylquinic acid)

3D SDF for CFc000220674 (3-O-Feruloylquinic acid)

3D-SDF for CFc000220674 (3-O-Feruloylquinic acid)

PDB for CFc000220674 (3-O-Feruloylquinic acid)

3D PDB for CFc000220674 (3-O-Feruloylquinic acid)

SMILES for CFc000220674 (3-O-Feruloylquinic acid)

INCHI for CFc000220674 (3-O-Feruloylquinic acid)

Structure for CFc000220674 (3-O-Feruloylquinic acid)

3D Structure for CFc000220674 (3-O-Feruloylquinic acid)