ChemFOnt: Showing chemical card for Cis-5-Caffeoylquinic acid (CFc000010523)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:59 UTC

Chemfont ID

CFc000010523

Molecule Identification

Common Name

Cis-5-Caffeoylquinic acid

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-O-(Z)-Caffeoylquinic acid	ChEBI
cis-5-O-Caffeoylquinic acid	ChEBI
cis-Chlorogenic acid	ChEBI
5-O-(Z)-Caffeoylquinate	Generator
cis-5-O-Caffeoylquinate	Generator
cis-Chlorogenate	Generator
cis-5-Caffeoylquinate	Generator
5-O-cis-Caffeoylquinate	Generator

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

IUPAC Name

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

Traditional Name

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

CAS Registry Number

327-97-9

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)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-/t11-,12-,14-,16+/m1/s1

InChI Key

CWVRJTMFETXNAD-XYXZIBEBSA-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

cinnamate ester (CHEBI:75489 )
cyclitol carboxylic acid (CHEBI:75489 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029278)
Cytoplasm (HMDB: HMDB0029278)

Source

Endogenous

Endogenous (HMDB: HMDB0029278)

Exogenous

Food

Food (HMDB: HMDB0029278)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Quince (FooDB: FOOD00069)

Exogenous (HMDB: HMDB0029278)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	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	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	31.87 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

HMDB0029278

DrugBank ID

Not Available

Phenol Explorer Compound ID

521

FooDB ID

FDB000275

KNApSAcK ID

Not Available

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

1794425

PDB ID

Not Available

ChEBI ID

75489

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cis-5-Caffeoylquinic acid (CFc000010523)

MOL for CFc000010523 (Cis-5-Caffeoylquinic acid)

3D MOL for CFc000010523 (Cis-5-Caffeoylquinic acid)

3D SDF for CFc000010523 (Cis-5-Caffeoylquinic acid)

3D-SDF for CFc000010523 (Cis-5-Caffeoylquinic acid)

PDB for CFc000010523 (Cis-5-Caffeoylquinic acid)

3D PDB for CFc000010523 (Cis-5-Caffeoylquinic acid)

SMILES for CFc000010523 (Cis-5-Caffeoylquinic acid)

INCHI for CFc000010523 (Cis-5-Caffeoylquinic acid)

Structure for CFc000010523 (Cis-5-Caffeoylquinic acid)

3D Structure for CFc000010523 (Cis-5-Caffeoylquinic acid)