ChemFOnt: Showing chemical card for 1-O-Caffeoylquinic acid (CFc000011860)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:45 UTC

Chemfont ID

CFc000011860

Molecule Identification

Common Name

1-O-Caffeoylquinic acid

Definition

1-O-Caffeoylquinic acid is found in coffee and coffee products. 1-O-Caffeoylquinic acid is a constituent of coffee

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-Caffeoylquinate	Generator
1-(3,4-Dihydroxycinnamoyl)quinic acid	HMDB
1-Caffeoylquinic acid	HMDB
1-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylate	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1241-87-8

SMILES

OC1CC(CC(O)C1O)(OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

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

InChI Key

GWTUHAXUUFROTF-RQOWECAXSA-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
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
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: HMDB0030652)
Cytoplasm (HMDB: HMDB0030652)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030652)

Source

Endogenous

Endogenous (HMDB: HMDB0030652)

Plant

Coffea (HMDB: HMDB0030652)

Exogenous

Food

Food (HMDB: HMDB0030652)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0030652)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.38 g/L	ALOGPS
logP	0.18	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.21	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	33.36 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

HMDB0030652

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002560

KNApSAcK ID

C00055231

Chemspider ID

35013249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751066

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-O-Caffeoylquinic acid (CFc000011860)

MOL for CFc000011860 (1-O-Caffeoylquinic acid)

3D MOL for CFc000011860 (1-O-Caffeoylquinic acid)

3D SDF for CFc000011860 (1-O-Caffeoylquinic acid)

3D-SDF for CFc000011860 (1-O-Caffeoylquinic acid)

PDB for CFc000011860 (1-O-Caffeoylquinic acid)

3D PDB for CFc000011860 (1-O-Caffeoylquinic acid)

SMILES for CFc000011860 (1-O-Caffeoylquinic acid)

INCHI for CFc000011860 (1-O-Caffeoylquinic acid)

Structure for CFc000011860 (1-O-Caffeoylquinic acid)

3D Structure for CFc000011860 (1-O-Caffeoylquinic acid)