ChemFOnt: Showing chemical card for stigmasterol 3-O-beta-D-glucoside (CFc000284007)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:47 UTC

Chemfont ID

CFc000284007

Molecule Identification

Common Name

stigmasterol 3-O-beta-D-glucoside

Definition

Stigmasterol 3-o-beta-d-glucoside, also known as poriferasterol monoglucoside or substance f, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmasterol 3-o-beta-d-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Stigmasterol 3-o-beta-d-glucoside can be found in a number of food items such as feijoa, star anise, quinoa, and mentha (mint), which makes stigmasterol 3-o-beta-d-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Stigmasterol 3-O-b-D-glucoside	Generator
Stigmasterol 3-O-β-D-glucoside	Generator
Stigmasterol-beta-D-glucoside	HMDB
Substance F	HMDB
Poriferasterol monoglucoside	HMDB

Chemical Formula

C₃₅H₅₈O₆

Average Molecular Weight

574.843

Monoisotopic Molecular Weight

574.423339588

IUPAC Name

2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C35H58O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h8-10,20-22,24-33,36-39H,7,11-19H2,1-6H3

InChI Key

VWDLOXMZIGUBKM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
Steroidal glycoside
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11606 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0038 g/L	ALOGPS
logP	5.3	ALOGPS
logP	5.71	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	163.3 m³·mol⁻¹	ChemAxon
Polarizability	69.1 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

HMDB0304491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031185

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

73072970

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for stigmasterol 3-O-beta-D-glucoside (CFc000284007)

MOL for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

3D MOL for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

3D SDF for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

3D-SDF for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

PDB for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

3D PDB for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

SMILES for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

INCHI for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

Structure for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)

3D Structure for CFc000284007 (stigmasterol 3-O-beta-D-glucoside)