ChemFOnt: Showing chemical card for Spinosterol (CFc000281789)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:31 UTC

Chemfont ID

CFc000281789

Molecule Identification

Common Name

Spinosterol

Definition

Spinosterol, also known as spinasterol, (3beta,5alpha,22e,24r)-isomer, 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. Thus, spinosterol is considered to be a sterol lipid molecule. Spinosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Spinosterol can be found in wild celery, which makes spinosterol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Spinasterol	Kegg
a-Spinasterol	HMDB
Α-spinasterol	HMDB
Spinasterol, (3beta,5alpha,22E,24R)-isomer	HMDB

Chemical Formula

C₂₉H₄₈O

Average Molecular Weight

412.702

Monoisotopic Molecular Weight

412.370516166

IUPAC Name

(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

Traditional Name

α-spinasterol

CAS Registry Number

481-18-5

SMILES

[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@]([H])(CC)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3/b9-8+/t20-,21-,22+,23+,25-,26+,27+,28+,29-/m1/s1

InChI Key

JZVFJDZBLUFKCA-FXIAWGAOSA-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

Triterpenoid
Stigmastane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:10333 )
stigmastane (C08840 )
Stigmasterols and C24-ethyl derivatives (C08840 )
Stigmasterols and C24-ethyl derivatives (LMST01040126 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302273)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.4e-05 g/L	ALOGPS
logP	7.46	ALOGPS
logP	7.48	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	53.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302273

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281331

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Spinosterol (CFc000281789)

MOL for CFc000281789 (Spinosterol)

3D MOL for CFc000281789 (Spinosterol)

3D SDF for CFc000281789 (Spinosterol)

3D-SDF for CFc000281789 (Spinosterol)

PDB for CFc000281789 (Spinosterol)

3D PDB for CFc000281789 (Spinosterol)

SMILES for CFc000281789 (Spinosterol)

INCHI for CFc000281789 (Spinosterol)

Structure for CFc000281789 (Spinosterol)

3D Structure for CFc000281789 (Spinosterol)