ChemFOnt: Showing chemical card for trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside (CFc000281469)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:53 UTC

Chemfont ID

CFc000281469

Molecule Identification

Common Name

trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside

Definition

Trans-p-ferulyl alcohol 4-o-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Trans-p-ferulyl alcohol 4-o-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Trans-p-ferulyl alcohol 4-o-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside can be found in a number of food items such as pepper (c. annuum), red bell pepper, yellow bell pepper, and italian sweet red pepper, which makes trans-p-ferulyl alcohol 4-o-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₁₀

Average Molecular Weight

428.4303

Monoisotopic Molecular Weight

428.168247116

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl 3-hydroxy-2-methylpropanoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl 3-hydroxy-2-methylpropanoate

CAS Registry Number

613232-82-9

SMILES

COC1=CC(\C=C\CO)=CC=C1O[C@@H]1O[C@H](COC(=O)C(C)CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H28O10/c1-11(9-22)19(26)28-10-15-16(23)17(24)18(25)20(30-15)29-13-6-5-12(4-3-7-21)8-14(13)27-2/h3-6,8,11,15-18,20-25H,7,9-10H2,1-2H3/b4-3+/t11?,15-,16-,17+,18-,20-/m1/s1

InChI Key

NUZPXHFCBKVLFX-QCIYUQLOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
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: HMDB0301953)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.42 g/L	ALOGPS
logP	0.05	ALOGPS
logP	-0.51	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.5	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	10	ChemAxon
Refractivity	103.91 m³·mol⁻¹	ChemAxon
Polarizability	43.21 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

HMDB0301953

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001667

KNApSAcK ID

Not Available

Chemspider ID

59696220

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101260573

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside (CFc000281469)

MOL for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

3D MOL for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

3D SDF for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

3D-SDF for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

PDB for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

3D PDB for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

SMILES for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

INCHI for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

Structure for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)

3D Structure for CFc000281469 (trans-p-Ferulyl alcohol 4-O-[6-(2-methyl-3-hydroxypropionyl)] glucopyranoside)