ChemFOnt: Showing chemical card for Caffeic acid 3-glucoside (CFc000282556)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:01 UTC

Chemfont ID

CFc000282556

Molecule Identification

Common Name

Caffeic acid 3-glucoside

Definition

Caffeic acid 3-glucoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Caffeic acid 3-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Caffeic acid 3-glucoside can be found in american cranberry, which makes caffeic acid 3-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caffeic acid 3-glucoside	ChEBI
trans-Caffeic acid 3-O-beta-D-glucoside	ChEBI
Caffeate 3-glucoside	Generator
trans-Caffeate 3-O-b-D-glucoside	Generator
trans-Caffeate 3-O-beta-D-glucoside	Generator
trans-Caffeate 3-O-β-D-glucoside	Generator
trans-Caffeic acid 3-O-b-D-glucoside	Generator
trans-Caffeic acid 3-O-β-D-glucoside	Generator
3-O-b-D-Glucosyl-trans-caffeate	Generator
3-O-b-D-Glucosyl-trans-caffeic acid	Generator
3-O-beta-D-Glucosyl-trans-caffeate	Generator
3-O-Β-D-glucosyl-trans-caffeate	Generator
3-O-Β-D-glucosyl-trans-caffeic acid	Generator

Chemical Formula

C₁₅H₁₈O₉

Average Molecular Weight

342.3

Monoisotopic Molecular Weight

342.09508216

IUPAC Name

(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

caffeic acid 3-glucoside

CAS Registry Number

24959-81-7

SMILES

[H]\C(=C(\[H])C1=CC(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1

InChI Key

QOPSZFXPZWQLOG-VHCZEJTMSA-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
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Styrene
Phenol ether
Phenoxy compound
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:3293 )
monosaccharide derivative (CHEBI:3293 )
hydroxycinnamic acid (CHEBI:3293 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303040)

Food

Fruit

Berry

American cranberry (FooDB: FOOD00192)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.24 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.74	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.17 m³·mol⁻¹	ChemAxon
Polarizability	32.44 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

HMDB0303040

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3293

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeic acid 3-glucoside (CFc000282556)

MOL for CFc000282556 (Caffeic acid 3-glucoside)

3D MOL for CFc000282556 (Caffeic acid 3-glucoside)

3D SDF for CFc000282556 (Caffeic acid 3-glucoside)

3D-SDF for CFc000282556 (Caffeic acid 3-glucoside)

PDB for CFc000282556 (Caffeic acid 3-glucoside)

3D PDB for CFc000282556 (Caffeic acid 3-glucoside)

SMILES for CFc000282556 (Caffeic acid 3-glucoside)

INCHI for CFc000282556 (Caffeic acid 3-glucoside)

Structure for CFc000282556 (Caffeic acid 3-glucoside)

3D Structure for CFc000282556 (Caffeic acid 3-glucoside)