ChemFOnt: Showing chemical card for 3,4-Di-O-caffeoylquinic acid (CFc000011911)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:49 UTC

Chemfont ID

CFc000011911

Molecule Identification

Common Name

3,4-Di-O-caffeoylquinic acid

Definition

3,4-Di-O-caffeoylquinic acid is found in arabica coffee. 3,4-Di-O-caffeoylquinic acid is isolated from coffe

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Di-O-caffeoylquinate	Generator
3,4-DICQA	MeSH
Isochlorogenic acid b	MeSH
Methyl 3,5-di-O-caffeoyl quinate	MeSH
Methyl-3,5-di-O-caffeoylquinate	MeSH
34-Dicaffeoylquinic acid	ChEMBL, HMDB
Rel-34-dicaffeoylquinic acid	ChEMBL, HMDB
34-Dicaffeoylquinate	Generator, HMDB
Rel-34-dicaffeoylquinate	Generator, HMDB
3,4-Dicaffeoylquinic acid	HMDB
4,5-Di-O-caffeoylquinic acid?	HMDB
Quinic acid 3,4-di-O-caffeate	HMDB
Isochlorogenate b	Generator
3,4-Di-O-caffeoylquinic acid	MeSH
3,4-Dicaffeoylquinate	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

IUPAC Name

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

Traditional Name

3,4-dicaffeoylquinic acid

CAS Registry Number

14534-61-3

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

UFCLZKMFXSILNL-PSEXTPKNSA-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
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Benzenoid
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quinic acid (CHEBI:5995 )
Caffeate derivatives (C10468 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17766198)

Cellular substructure

Extracellular (HMDB: HMDB0030705)
Cytoplasm (HMDB: HMDB0030705)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030705)

Source

Endogenous

Endogenous (HMDB: HMDB0030705)

Plant

Plant (HMDB: HMDB0030705)
Coffea (HMDB: HMDB0030705)

Exogenous

Food

Food (HMDB: HMDB0030705)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Vegetables (HMDB: HMDB0030705)

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0030705)

Coffee and coffee products (FooDB: FOOD00861)

Tea

Tea products (HMDB: HMDB0030705)

Fruit

Fruits (HMDB: HMDB0030705)

Pome

Asian pear (FooDB: FOOD00291)

Exogenous (HMDB: HMDB0030705)

Process

Not Available

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.05	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	49.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon