ChemFOnt: Showing chemical card for 1-O-Cinnamoylglucose (CFc000336909)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:20 UTC

Chemfont ID

CFc000336909

Molecule Identification

Common Name

1-O-Cinnamoylglucose

Definition

1-o-e-cinnamoylglucose is a member of the class of compounds known as O-cinnamoyl glycosides. O-cinnamoyl glycosides are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 1-o-e-cinnamoylglucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-e-cinnamoylglucose can be found in fruits, which makes 1-o-e-cinnamoylglucose a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-1-O-Cinnamoyl-b-D-glucose	Generator
(e)-1-O-Cinnamoyl-β-D-glucose	Generator
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-phenylprop-2-enoic acid	HMDB

Chemical Formula

C₁₅H₁₈O₇

Average Molecular Weight

310.2992

Monoisotopic Molecular Weight

310.10525293

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

41682-52-4

SMILES

OCC1OC(OC(=O)\C=C\C2=CC=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H18O7/c16-8-10-12(18)13(19)14(20)15(21-10)22-11(17)7-6-9-4-2-1-3-5-9/h1-7,10,12-16,18-20H,8H2/b7-6+

InChI Key

CJGRGYBLAHPYOM-VOTSOKGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-cinnamoyl glycosides. These are o-glycoside derivatives of cinnamic acid. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

O-cinnamoyl glycosides

Alternative Parents

Substituents

O-cinnamoyl glycoside
Hexose monosaccharide
Styrene
Fatty acid ester
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0030293)

Food

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.42 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	0.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.49 m³·mol⁻¹	ChemAxon
Polarizability	31.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030293

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021748

KNApSAcK ID

C00058319

Chemspider ID

24785656

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5797730

PDB ID

Not Available

ChEBI ID

167947

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-O-Cinnamoylglucose (CFc000336909)

MOL for CFc000336909 (1-O-Cinnamoylglucose)

3D MOL for CFc000336909 (1-O-Cinnamoylglucose)

3D SDF for CFc000336909 (1-O-Cinnamoylglucose)

3D-SDF for CFc000336909 (1-O-Cinnamoylglucose)

PDB for CFc000336909 (1-O-Cinnamoylglucose)

3D PDB for CFc000336909 (1-O-Cinnamoylglucose)

SMILES for CFc000336909 (1-O-Cinnamoylglucose)

INCHI for CFc000336909 (1-O-Cinnamoylglucose)

Structure for CFc000336909 (1-O-Cinnamoylglucose)

3D Structure for CFc000336909 (1-O-Cinnamoylglucose)