ChemFOnt: Showing chemical card for (22alpha)-hydroxy-sitosterol (CFc000283476)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:47 UTC

Chemfont ID

CFc000283476

Molecule Identification

Common Name

(22alpha)-hydroxy-sitosterol

Definition

(22alpha)-hydroxy-sitosterol 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 (22alpha)-hydroxy-sitosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (22alpha)-hydroxy-sitosterol can be found in a number of food items such as cottonseed, oil-seed camellia, cloves, and dill, which makes (22alpha)-hydroxy-sitosterol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(22a)-Hydroxy-sitosterol	Generator
(22Α)-hydroxy-sitosterol	Generator
Itesmol	MeSH

Chemical Formula

C₂₉H₅₀O₂

Average Molecular Weight

430.717

Monoisotopic Molecular Weight

430.38108085

IUPAC Name

14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

CCC(CC(O)C(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C

InChI Identifier

InChI=1S/C29H50O2/c1-7-20(18(2)3)16-27(31)19(4)24-10-11-25-23-9-8-21-17-22(30)12-14-28(21,5)26(23)13-15-29(24,25)6/h8,18-20,22-27,30-31H,7,9-17H2,1-6H3

InChI Key

YCZQDKIUGZGCAN-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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
22-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a triterpenoid (CPD-7190 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.05	ALOGPS
logP	6.54	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.36 m³·mol⁻¹	ChemAxon
Polarizability	54.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0303960

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030100

KNApSAcK ID

Not Available

Chemspider ID

166039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

191199

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (22alpha)-hydroxy-sitosterol (CFc000283476)

MOL for CFc000283476 ((22alpha)-hydroxy-sitosterol)

3D MOL for CFc000283476 ((22alpha)-hydroxy-sitosterol)

3D SDF for CFc000283476 ((22alpha)-hydroxy-sitosterol)

3D-SDF for CFc000283476 ((22alpha)-hydroxy-sitosterol)

PDB for CFc000283476 ((22alpha)-hydroxy-sitosterol)

3D PDB for CFc000283476 ((22alpha)-hydroxy-sitosterol)

SMILES for CFc000283476 ((22alpha)-hydroxy-sitosterol)

INCHI for CFc000283476 ((22alpha)-hydroxy-sitosterol)

Structure for CFc000283476 ((22alpha)-hydroxy-sitosterol)

3D Structure for CFc000283476 ((22alpha)-hydroxy-sitosterol)