ChemFOnt: Showing chemical card for Caffeic acid 4-O-glucuronide (CFc000022568)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:56 UTC

Chemfont ID

CFc000022568

Molecule Identification

Common Name

Caffeic acid 4-O-glucuronide

Definition

Caffeic acid 4-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caffeate 4-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₅H₁₆O₁₀

Average Molecular Weight

356.2815

Monoisotopic Molecular Weight

356.074346732

IUPAC Name

(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

O[C@H]1[C@H](OC2=C(O)C=C(\C=C\C(O)=O)C=C2)O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C15H16O10/c16-7-5-6(2-4-9(17)18)1-3-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+/t10-,11-,12+,13-,15+/m0/s1

InChI Key

LTGOIJNQWZWJRF-ZYZFHZPYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavanol
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0041707)
Kidney (HMDB: HMDB0041707)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0041707)
Cytoplasm (HMDB: HMDB0041707)

Source

Endogenous

Endogenous (HMDB: HMDB0041707)

Exogenous

Food

Food (HMDB: HMDB0041707)
Legumes (HMDB: HMDB0041707)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041707)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0041707)

Tea

Tea products (HMDB: HMDB0041707)

Fat and oil

Olive oil (HMDB: HMDB0041707)

Fruit

Fruits (HMDB: HMDB0041707)

Vegetable

Vegetables (HMDB: HMDB0041707)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0041707)

Nut

Nuts (HMDB: HMDB0041707)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041707)

Exogenous (HMDB: HMDB0041707)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0041707)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.1 g/L	ALOGPS
logP	0.71	ALOGPS
logP	-0.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.03 m³·mol⁻¹	ChemAxon
Polarizability	32.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041707

DrugBank ID

Not Available

Phenol Explorer Compound ID

946

FooDB ID

FDB029872

KNApSAcK ID

Not Available

Chemspider ID

30777606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25171780

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeic acid 4-O-glucuronide (CFc000022568)

MOL for CFc000022568 (Caffeic acid 4-O-glucuronide)

3D MOL for CFc000022568 (Caffeic acid 4-O-glucuronide)

3D SDF for CFc000022568 (Caffeic acid 4-O-glucuronide)

3D-SDF for CFc000022568 (Caffeic acid 4-O-glucuronide)

PDB for CFc000022568 (Caffeic acid 4-O-glucuronide)

3D PDB for CFc000022568 (Caffeic acid 4-O-glucuronide)

SMILES for CFc000022568 (Caffeic acid 4-O-glucuronide)

INCHI for CFc000022568 (Caffeic acid 4-O-glucuronide)

Structure for CFc000022568 (Caffeic acid 4-O-glucuronide)

3D Structure for CFc000022568 (Caffeic acid 4-O-glucuronide)