ChemFOnt: Showing chemical card for beta-Sitosterol 3-O-beta-D-Glucuronopyranoside (CFc000336862)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:15 UTC

Chemfont ID

CFc000336862

Molecule Identification

Common Name

beta-Sitosterol 3-O-beta-D-Glucuronopyranoside

Definition

Beta-sitosterol 3-o-beta-d-glucuronopyranoside is a member of the class of compounds known as steroid glucuronide conjugates. Steroid glucuronide conjugates are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Beta-sitosterol 3-o-beta-d-glucuronopyranoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Beta-sitosterol 3-o-beta-d-glucuronopyranoside can be found in a number of food items such as dill, bitter gourd, dandelion, and german camomile, which makes beta-sitosterol 3-o-beta-d-glucuronopyranoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
b-Sitosterol 3-O-b-D-glucuronopyranoside	Generator
Β-sitosterol 3-O-β-D-glucuronopyranoside	Generator

Chemical Formula

C₃₅H₅₈O₇

Average Molecular Weight

590.8308

Monoisotopic Molecular Weight

590.41825421

IUPAC Name

6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

126251-01-2

SMILES

CCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(C(O)C(O)C1O)C(O)=O)C(C)C

InChI Identifier

InChI=1S/C35H58O7/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(14-16-34(22,5)27(24)15-17-35(25,26)6)41-33-30(38)28(36)29(37)31(42-33)32(39)40/h10,19-21,23-31,33,36-38H,7-9,11-18H2,1-6H3,(H,39,40)

InChI Key

REARGUUVUPUXPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Steroid-glucuronide-skeleton
Stigmastane-skeleton
Triterpenoid
Delta-5-steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Polyol
Acetal
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (FooDB: )

Cloves (FooDB: FOOD00179)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Gourd

Bitter gourd (FooDB: FOOD00115)

Process

Not Available

Role

Biological role

Anti spasmodic (FooDB: )

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (FooDB: )

Convulsant (FooDB: )

Central nervous system depressant (FooDB: )
Central nervous system stimulant (FooDB: )
Hypoglycemic agent (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	6.05	ALOGPS
logP	6.39	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	162.05 m³·mol⁻¹	ChemAxon
Polarizability	69.95 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0168484

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021626

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4447509

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for beta-Sitosterol 3-O-beta-D-Glucuronopyranoside (CFc000336862)

MOL for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

3D MOL for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

3D SDF for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

3D-SDF for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

PDB for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

3D PDB for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

SMILES for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

INCHI for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

Structure for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)

3D Structure for CFc000336862 (beta-Sitosterol 3-O-beta-D-Glucuronopyranoside)