ChemFOnt: Showing chemical card for 1-O-Sinapoyl-beta-D-glucose (CFc000281895)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:44 UTC

Chemfont ID

CFc000281895

Molecule Identification

Common Name

1-O-Sinapoyl-beta-D-glucose

Definition

1-o-sinapoyl-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-sinapoyl-beta-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-sinapoyl-beta-d-glucose can be found in a number of food items such as white cabbage, corn, common pea, and cabbage, which makes 1-o-sinapoyl-beta-d-glucose a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylATE	ChEBI
1-O-(trans-Sinapoyl)-beta-D-glucose	ChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucopyranose	ChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucose	ChEBI
1-O-[(e)-Sinapoyl]-beta-D-glucopyranose	ChEBI
1-O-Sinapoyl beta-D-glucoside	ChEBI
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acid	Generator
1-O-(trans-Sinapoyl)-b-D-glucose	Generator
1-O-(trans-Sinapoyl)-β-D-glucose	Generator
1-O-[(2E)-Sinapoyl]-b-D-glucopyranose	Generator
1-O-[(2E)-Sinapoyl]-β-D-glucopyranose	Generator
1-O-[(2E)-Sinapoyl]-b-D-glucose	Generator
1-O-[(2E)-Sinapoyl]-β-D-glucose	Generator
1-O-[(e)-Sinapoyl]-b-D-glucopyranose	Generator
1-O-[(e)-Sinapoyl]-β-D-glucopyranose	Generator
1-O-Sinapoyl b-D-glucoside	Generator
1-O-Sinapoyl β-D-glucoside	Generator
1-O-Sinapoyl-b-D-glucose	Generator
1-O-Sinapoyl-β-D-glucose	Generator

Chemical Formula

C₁₇H₂₂O₁₀

Average Molecular Weight

386.3506

Monoisotopic Molecular Weight

386.121296924

IUPAC Name

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

Traditional Name

1-O-sinapoyl-β-D-glucose

CAS Registry Number

None

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1

InChI Key

XRKBRPFTFKKHEF-DGDBGZAXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Hexose monosaccharide
Cinnamic acid ester
Coumaric acid or derivatives
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Phenoxy compound
Anisole
Styrene
Phenol ether
Fatty acid ester
Alkyl aryl ether
Phenol
Fatty acyl
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:16546 )
cinnamate ester (CHEBI:16546 )
dimethoxybenzene (CHEBI:16546 )
glucosyl hydroxycinnamic acid (CHEBI:16546 )
Sinapate derivatives (C01175 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302379)

Food

Vegetable

Cabbage

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.47 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-0.52	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.4 m³·mol⁻¹	ChemAxon
Polarizability	38.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302379

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

16546

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-O-Sinapoyl-beta-D-glucose (CFc000281895)

MOL for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

3D MOL for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

3D SDF for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

3D-SDF for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

PDB for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

3D PDB for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

SMILES for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

INCHI for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

Structure for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)

3D Structure for CFc000281895 (1-O-Sinapoyl-beta-D-glucose)