ChemFOnt: Showing chemical card for 3,5-Di-O-caffeoylquinic acid (CFc000011912)

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

CFc000011912

Molecule Identification

Common Name

3,5-Di-O-caffeoylquinic acid

Definition

3,5-Di-O-caffeoylquinic acid is found in arabica coffee. 3,5-Di-O-caffeoylquinic acid is isolated from coffee, globe artichoke (Cynara scolymus) and caucasian whortleberry (Vaccinium arctostaphylos

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate	ChEBI
3,5-DCQA	ChEBI
3,5-Dicaffeoylquinic acid	ChEBI
Isochlorogenic acid a	ChEBI
Quinic acid 3,5-di-O-caffeate	ChEBI
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoic acid	Generator
3,5-Dicaffeoylquinate	Generator
Isochlorogenate a	Generator
Quinate 3,5-di-O-caffeate	Generator
Quinic acid 3,5-di-O-caffeic acid	Generator
Dicaffeoylquinate	Generator
3,5-Di-O-caffeoyl quinate	Generator
3,5-Di-O-caffeoylquinate	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

IUPAC Name

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

Traditional Name

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

CAS Registry Number

2450-53-5

SMILES

O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[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(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

KRZBCHWVBQOTNZ-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

carboxylic ester (CHEBI:65751 )
cyclitol carboxylic acid (CHEBI:65751 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17766198)

Cellular substructure

Extracellular (HMDB: HMDB0030706)
Cytoplasm (HMDB: HMDB0030706)

Source

Exogenous

Exogenous (HMDB: HMDB0030706)

Food

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Green vegetables (FooDB: FOOD00872)

Root vegetable

Carrot (FooDB: FOOD00245)

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

Coffee and coffee products (FooDB: FOOD00861)

Fruit

Pome

Quince (FooDB: FOOD00069)

Fruits (FooDB: FOOD00871)

Endogenous

Endogenous (HMDB: HMDB0030706)

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)	3.28	ChemAxon
pKa (Strongest Basic)	-3.6	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	49.46 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

External Links

HMDB ID

HMDB0029280

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002628

KNApSAcK ID

C00002733

Chemspider ID

22912767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cynarine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65751

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,5-Di-O-caffeoylquinic acid (CFc000011912)

MOL for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

3D MOL for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

3D SDF for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

3D-SDF for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

PDB for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

3D PDB for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

SMILES for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

INCHI for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

Structure for CFc000011912 (3,5-Di-O-caffeoylquinic acid)

3D Structure for CFc000011912 (3,5-Di-O-caffeoylquinic acid)