ChemFOnt: Showing chemical card for 4-O-Caffeoyl-3-O-feruloylquinic acid (CFc000014107)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:02:41 UTC

Chemfont ID

CFc000014107

Molecule Identification

Common Name

4-O-Caffeoyl-3-O-feruloylquinic acid

Definition

4-O-Caffeoyl-3-O-feruloylquinic acid is found in coffee and coffee products. 4-O-Caffeoyl-3-O-feruloylquinic acid is a constituent of coffee beans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-Caffeoyl-3-O-feruloylquinate	Generator
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3-dihydroxy-5-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	Generator
3-Feruloyl-4-caffeoylquinate	Generator

Chemical Formula

C₂₆H₂₆O₁₂

Average Molecular Weight

530.4774

Monoisotopic Molecular Weight

530.142426296

IUPAC Name

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

Traditional Name

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

CAS Registry Number

96990-65-7

SMILES

COC1=C(O)C=CC(\C=C/C(=O)OC2CC(O)(CC(O)C2OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C(O)=O)=C1

InChI Identifier

InChI=1S/C26H26O12/c1-36-20-11-15(3-7-17(20)28)5-8-22(31)37-21-13-26(35,25(33)34)12-19(30)24(21)38-23(32)9-4-14-2-6-16(27)18(29)10-14/h2-11,19,21,24,27-30,35H,12-13H2,1H3,(H,33,34)/b8-5-,9-4-

InChI Key

SDMADMBVKYOYQN-QWUBYWPLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Phenolic glycoside
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Pyranone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Dialkyl ether
Ether
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033008)
Cell membrane (HMDB: HMDB0033008)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033008)

Source

Exogenous

Exogenous (HMDB: HMDB0033008)

Food

Food (HMDB: HMDB0033008)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0033008)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033008)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.065 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.3	ChemAxon
logS	-3.9	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	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.25 m³·mol⁻¹	ChemAxon
Polarizability	50.47 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

HMDB0033008

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010998

KNApSAcK ID

Not Available

Chemspider ID

35013523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751357

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-O-Caffeoyl-3-O-feruloylquinic acid (CFc000014107)

MOL for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

3D MOL for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

3D SDF for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

3D-SDF for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

PDB for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

3D PDB for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

SMILES for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

INCHI for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

Structure for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)

3D Structure for CFc000014107 (4-O-Caffeoyl-3-O-feruloylquinic acid)