ChemFOnt: Showing chemical card for Dihydrocaffeic acid 3-O-glucuronide (CFc000022581)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:57 UTC

Chemfont ID

CFc000022581

Molecule Identification

Common Name

Dihydrocaffeic acid 3-O-glucuronide

Definition

Dihydrocaffeic acid 3-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dihydrocaffeate 3-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-6-[5-(2-Carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₅H₁₈O₁₀

Average Molecular Weight

358.2974

Monoisotopic Molecular Weight

358.089996796

IUPAC Name

(2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m0/s1

InChI Key

AELQNMHOLDHBFA-DKBOKBLXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
3-phenylpropanoic-acid
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Hydroxy acid
Pyran
Oxane
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Monosaccharide
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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: HMDB0041720)
Kidney (HMDB: HMDB0041720)

Excreta

Biofluid or Excreta

Urine (PMID: 19460943)

Cellular substructure

Extracellular (HMDB: HMDB0041720)
Cytoplasm (HMDB: HMDB0041720)

Source

Endogenous

Endogenous (HMDB: HMDB0041720)

Exogenous

Food

Food (HMDB: HMDB0041720)
Legumes (HMDB: HMDB0041720)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041720)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0041720)

Tea

Tea products (HMDB: HMDB0041720)

Fat and oil

Olive oil (HMDB: HMDB0041720)

Fruit

Fruits (HMDB: HMDB0041720)

Vegetable

Vegetables (HMDB: HMDB0041720)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0041720)

Nut

Nuts (HMDB: HMDB0041720)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041720)

Exogenous (HMDB: HMDB0041720)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0041720)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.41 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-0.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.01	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	6	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	32.59 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

HMDB0041720

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029886

KNApSAcK ID

Not Available

Chemspider ID

30777618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49844972

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dihydrocaffeic acid 3-O-glucuronide (CFc000022581)

MOL for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

3D MOL for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

3D SDF for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

3D-SDF for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

PDB for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

3D PDB for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

SMILES for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

INCHI for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

Structure for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)

3D Structure for CFc000022581 (Dihydrocaffeic acid 3-O-glucuronide)