ChemFOnt: Showing chemical card for 3-Feruloylquinic acid (CFc000011877)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:46 UTC

Chemfont ID

CFc000011877

Molecule Identification

Common Name

3-Feruloylquinic acid

Definition

3-Feruloylquinic acid (3-FQA) (CAS: 1899-29-2) belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Coffee, especially green or raw coffee, is a major source of chlorogenic acids (CGA). CGAs have been associated with a range of health benefits including a reduction in the risk of cardiovascular disease, diabetes type 2, and Alzheimer's disease. Major CGAs in coffee include 3-, 4-, and 5-feruloylquinic acids (PMID: 19022950 ). 3-FQA has been detected in the plasma and urine of humans who have ingested coffee (PMID: 19460943 ). 3-FQA is also found in chicory, tomatoes (Lycopersicon esculentum), and sunflowers (Helianthus annuus).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-Feruloylquinate	Generator
3-Ferulylquinic acid	HMDB
1,3,4-Trihydroxy-5-{[(2Z)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	Generator

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.3353

Monoisotopic Molecular Weight

368.110732238

IUPAC Name

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

Traditional Name

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

CAS Registry Number

62929-69-5

SMILES

COC1=C(O)C=C(\C=C/C(=O)OC2CC(O)(CC(O)C2O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C17H20O9/c1-25-12-4-2-9(6-10(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-

InChI Key

ZHBZPCLRULAFBL-HYXAFXHYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Ether
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19460943)

Excreta

Biofluid or Excreta

Urine (PMID: 26269369)

Cellular substructure

Extracellular (HMDB: HMDB0030669)
Cytoplasm (HMDB: HMDB0030669)

Source

Endogenous

Endogenous (HMDB: HMDB0030669)

Exogenous

Exogenous (HMDB: HMDB0030669)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Drupe

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)

Fruits (HMDB: HMDB0030669)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Vegetables (HMDB: HMDB0030669)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0030669)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Tea

Tea products (HMDB: HMDB0030669)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.16 g/L	ALOGPS
logP	0.25	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	35.39 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

HMDB0030669

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002583

KNApSAcK ID

C00035939

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

131751068

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Feruloylquinic acid (CFc000011877)

MOL for CFc000011877 (3-Feruloylquinic acid)

3D MOL for CFc000011877 (3-Feruloylquinic acid)

3D SDF for CFc000011877 (3-Feruloylquinic acid)

3D-SDF for CFc000011877 (3-Feruloylquinic acid)

PDB for CFc000011877 (3-Feruloylquinic acid)

3D PDB for CFc000011877 (3-Feruloylquinic acid)

SMILES for CFc000011877 (3-Feruloylquinic acid)

INCHI for CFc000011877 (3-Feruloylquinic acid)

Structure for CFc000011877 (3-Feruloylquinic acid)

3D Structure for CFc000011877 (3-Feruloylquinic acid)