ChemFOnt: Showing chemical card for Glucocaffeic acid (CFc000015390)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:32 UTC

Chemfont ID

CFc000015390

Molecule Identification

Common Name

Glucocaffeic acid

Definition

Glucocaffeic acid is found in blackcurrant. Glucocaffeic acid is isolated from flax (Linum usitatissimum

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glucocaffeate	Generator
Caffeic acid 4-O-glucoside	HMDB
Linocaffein	HMDB
(2E)-3-(3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator

Chemical Formula

C₁₅H₁₈O₉

Average Molecular Weight

342.298

Monoisotopic Molecular Weight

342.095082174

IUPAC Name

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

Traditional Name

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

CAS Registry Number

17093-82-2

SMILES

OCC1OC(OC2=C(O)C=C(\C=C\C(O)=O)C=C2)C(O)C(O)C1O

InChI Identifier

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

InChI Key

OHEYCHKLBCPRLZ-DUXPYHPUSA-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
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034313)
Cytoplasm (HMDB: HMDB0034313)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034313)

Source

Exogenous

Exogenous (HMDB: HMDB0034313)

Food

Food (HMDB: HMDB0034313)

Fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Tea

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034313)
Coffea (HMDB: HMDB0034313)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034313)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.92 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.74	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.46	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	32.69 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

HMDB0034313

DrugBank ID

Not Available

Phenol Explorer Compound ID

488

FooDB ID

FDB012662

KNApSAcK ID

Not Available

Chemspider ID

4823601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6148082

PDB ID

Not Available

ChEBI ID

143038

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glucocaffeic acid (CFc000015390)

MOL for CFc000015390 (Glucocaffeic acid)

3D MOL for CFc000015390 (Glucocaffeic acid)

3D SDF for CFc000015390 (Glucocaffeic acid)

3D-SDF for CFc000015390 (Glucocaffeic acid)

PDB for CFc000015390 (Glucocaffeic acid)

3D PDB for CFc000015390 (Glucocaffeic acid)

SMILES for CFc000015390 (Glucocaffeic acid)

INCHI for CFc000015390 (Glucocaffeic acid)

Structure for CFc000015390 (Glucocaffeic acid)

3D Structure for CFc000015390 (Glucocaffeic acid)