ChemFOnt: Showing chemical card for trans-p-Coumaroyl beta-D-glucopyranoside (CFc000281605)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:10 UTC

Chemfont ID

CFc000281605

Molecule Identification

Common Name

trans-p-Coumaroyl beta-D-glucopyranoside

Definition

Trans-p-coumaroyl beta-d-glucopyranoside, also known as 1-O-(4-hydroxycinnamoyl)-beta-D-glucose or 1-O-(4-coumaroyl)-β-D-glucoside, is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. Trans-p-coumaroyl beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-p-coumaroyl beta-d-glucopyranoside can be found in tea, which makes trans-p-coumaroyl beta-d-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-(4-Hydroxycinnamoyl)-beta-D-glucose	ChEBI
1-O-(trans-4-Coumaroyl)-beta-D-glucose	ChEBI
p-Coumaroyl-beta-D-glucose	ChEBI
1-O-(4-Hydroxycinnamoyl)-b-D-glucose	Generator
1-O-(4-Hydroxycinnamoyl)-β-D-glucose	Generator
1-O-(trans-4-Coumaroyl)-b-D-glucose	Generator
1-O-(trans-4-Coumaroyl)-β-D-glucose	Generator
p-Coumaroyl-b-D-glucose	Generator
p-Coumaroyl-β-D-glucose	Generator
1-O-(4-Coumaroyl)-b-D-glucose	Generator
1-O-(4-Coumaroyl)-β-D-glucose	Generator
trans-P-Coumaroyl b-D-glucopyranoside	Generator
trans-P-Coumaroyl β-D-glucopyranoside	Generator
1-O-(4-Coumaroyl)-beta-D-glucose	KEGG

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

IUPAC Name

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

Traditional Name

p-coumaroyl-D-glucose

CAS Registry Number

13080-39-2

SMILES

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

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-17,19-21H,7H2/b6-3+/t10-,12-,13+,14-,15+/m1/s1

InChI Key

DSNCQKUYZOSARM-QVLXMGEUSA-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
Coumaric acid ester
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

O-acyl carbohydrate (CHEBI:71498 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302089)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.2 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.47 m³·mol⁻¹	ChemAxon
Polarizability	32.26 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

HMDB0302089

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093521

KNApSAcK ID

Not Available

Chemspider ID

10394547

KEGG Compound ID

C16827

BioCyc ID

CPD-8674

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71498

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for trans-p-Coumaroyl beta-D-glucopyranoside (CFc000281605)

MOL for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D MOL for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D SDF for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D-SDF for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

PDB for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D PDB for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

SMILES for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

INCHI for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

Structure for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)

3D Structure for CFc000281605 (trans-p-Coumaroyl beta-D-glucopyranoside)