ChemFOnt: Showing chemical card for 5Z-Caffeoylquinic acid (CFc000021561)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:24 UTC

Chemfont ID

CFc000021561

Molecule Identification

Common Name

5Z-Caffeoylquinic acid

Definition

5Z-Caffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5Z-Caffeoylquinate	Generator
trans-Neochlorogenic acid	HMDB
3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate	HMDB
(1S,3R,4S,5R)-3-(((2E)-3-(3,4-Dihydroxyphenyl)-2-propenoyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid	HMDB
Isochlorogenic acid	HMDB
trans-Neochlorogenate	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

IUPAC Name

3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Traditional Name

chlorogenic acid

CAS Registry Number

32719-11-2

SMILES

[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC1CC(O)(CC(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+

InChI Key

CWVRJTMFETXNAD-DUXPYHPUSA-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
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
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

Cellular substructure

Extracellular (HMDB: HMDB0040690)
Cytoplasm (HMDB: HMDB0040690)

Source

Exogenous

Exogenous (HMDB: HMDB0040690)

Food

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Fruit

Pome

Pear (FooDB: FOOD00152)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
logP	-0.27	ChemAxon
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040690

DrugBank ID

Not Available

Phenol Explorer Compound ID

571

FooDB ID

FDB004038

KNApSAcK ID

Not Available

Chemspider ID

4475041

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315832

PDB ID

Not Available

ChEBI ID

143036

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5Z-Caffeoylquinic acid (CFc000021561)

MOL for CFc000021561 (5Z-Caffeoylquinic acid)

3D MOL for CFc000021561 (5Z-Caffeoylquinic acid)

3D SDF for CFc000021561 (5Z-Caffeoylquinic acid)

3D-SDF for CFc000021561 (5Z-Caffeoylquinic acid)

PDB for CFc000021561 (5Z-Caffeoylquinic acid)

3D PDB for CFc000021561 (5Z-Caffeoylquinic acid)

SMILES for CFc000021561 (5Z-Caffeoylquinic acid)

INCHI for CFc000021561 (5Z-Caffeoylquinic acid)

Structure for CFc000021561 (5Z-Caffeoylquinic acid)

3D Structure for CFc000021561 (5Z-Caffeoylquinic acid)