ChemFOnt: Showing chemical card for (22alpha)-hydroxy-isofucosterol (CFc000283475)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:46 UTC

Chemfont ID

CFc000283475

Molecule Identification

Common Name

(22alpha)-hydroxy-isofucosterol

Definition

(22alpha)-hydroxy-isofucosterol 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-isofucosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (22alpha)-hydroxy-isofucosterol can be found in a number of food items such as garden onion (variety), sunflower, mammee apple, and prickly pear, which makes (22alpha)-hydroxy-isofucosterol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(22a)-Hydroxy-isofucosterol	Generator
(22Α)-hydroxy-isofucosterol	Generator

Chemical Formula

C₂₉H₄₈O₂

Average Molecular Weight

428.701

Monoisotopic Molecular Weight

428.365430786

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H48O2/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/h7-8,18-19,22-27,30-31H,9-17H2,1-6H3

InChI Key

IYBGBNAVLWUPQU-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-7191 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	6.23	ALOGPS
logP	6.13	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.63	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	5	ChemAxon
Refractivity	132.21 m³·mol⁻¹	ChemAxon
Polarizability	53.76 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	No	ChemAxon

External Links

HMDB ID

HMDB0303959

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030099

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

74413736

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (22alpha)-hydroxy-isofucosterol (CFc000283475)

MOL for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

3D MOL for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

3D SDF for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

3D-SDF for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

PDB for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

3D PDB for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

SMILES for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

INCHI for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

Structure for CFc000283475 ((22alpha)-hydroxy-isofucosterol)

3D Structure for CFc000283475 ((22alpha)-hydroxy-isofucosterol)