ChemFOnt: Showing chemical card for 1-O-Caffeoyl-beta-D-glucose (CFc000281956)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:51 UTC

Chemfont ID

CFc000281956

Molecule Identification

Common Name

1-O-Caffeoyl-beta-D-glucose

Definition

1-o-caffeoyl-beta-d-glucose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1-o-caffeoyl-beta-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-caffeoyl-beta-d-glucose can be found in a number of food items such as wild leek, garden onion, orange bell pepper, and green bell pepper, which makes 1-o-caffeoyl-beta-d-glucose a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-[(e)-Caffeoyl]-beta-D-glucose	ChEBI
1-O-[(e)-Caffeoyl]-b-D-glucose	Generator
1-O-[(e)-Caffeoyl]-β-D-glucose	Generator
1-Caffeoyl-b-D-glucose	Generator
1-Caffeoyl-β-D-glucose	Generator
1-O-(trans-Caffeoyl)-beta-D-glucose	ChEBI
1-O-(trans-Caffeoyl)-b-D-glucose	Generator
1-O-(trans-Caffeoyl)-β-D-glucose	Generator
1-O-Caffeoyl-b-D-glucose	Generator
1-O-Caffeoyl-β-D-glucose	Generator

Chemical Formula

C₁₅H₁₈O₉

Average Molecular Weight

342.298

Monoisotopic Molecular Weight

342.095082174

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

1-caffeoyl-β-D-glucose

CAS Registry Number

14364-08-0

SMILES

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

InChI Identifier

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

InChI Key

WQSDYZZEIBAPIN-VBQORRLJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302440)

Food

Vegetable

Fruit vegetable

Onion-family vegetable

Wild leek (FooDB: FOOD00396)
Garden onion (FooDB: FOOD00006)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.98 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-0.51	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.45 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