ChemFOnt: Showing chemical card for 4-Feruloylquinic acid (CFc000220706)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:00 UTC

Chemfont ID

CFc000220706

Molecule Identification

Common Name

4-Feruloylquinic acid

Definition

4-Feruloylquinic acid (4-FQA) (CAS: 2613-86-7) 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 ). 4-FQA has been detected in the plasma and urine of humans who have ingested coffee (PMID: 19460943 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Feruloylquinate	ChEBI
O-Feruloylquinic acid	Generator
4-Feruloylquinate	Generator
4-O-Feruloylquinic acid	HMDB
4-FQA	HMDB
4-O-(e)-Feruloylquinic acid	HMDB
trans-4-O-Feruloyl quinic acid	HMDB
trans-4-O-Feruloylquinic acid	HMDB
4-Feruloylquinic acid	HMDB

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.3353

Monoisotopic Molecular Weight

368.110732238

IUPAC Name

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

Traditional Name

4-O-feruloyl-D-quinic acid

CAS Registry Number

96646-16-1

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enoate ester (CHEBI:18013 )
quinic acid (CHEBI:18013 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19460943)

Excreta

Biofluid or Excreta

Urine (PMID: 19460943)

Source

Exogenous

Exogenous (HMDB: HMDB0240453)

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: HMDB0240453)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Vegetables (HMDB: HMDB0240453)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0240453)

Tea

Tea products (HMDB: HMDB0240453)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.8 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.12	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.39	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	35.51 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

HMDB0240453

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000248

KNApSAcK ID

C00055232

Chemspider ID

10392638

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

18013

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-Feruloylquinic acid (CFc000220706)

MOL for CFc000220706 (4-Feruloylquinic acid)

3D MOL for CFc000220706 (4-Feruloylquinic acid)

3D SDF for CFc000220706 (4-Feruloylquinic acid)

3D-SDF for CFc000220706 (4-Feruloylquinic acid)

PDB for CFc000220706 (4-Feruloylquinic acid)

3D PDB for CFc000220706 (4-Feruloylquinic acid)

SMILES for CFc000220706 (4-Feruloylquinic acid)

INCHI for CFc000220706 (4-Feruloylquinic acid)

Structure for CFc000220706 (4-Feruloylquinic acid)

3D Structure for CFc000220706 (4-Feruloylquinic acid)