Showing Compound beta-Sitostenone (FDB012138)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:00 UTC

Update date

2019-11-26 03:06:15 UTC

Primary ID

FDB012138

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

beta-Sitostenone

Description

beta-Sitostenone, also known as β-sitostenone, 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. Based on a literature review a significant number of articles have been published on beta-Sitostenone.

CAS Number

1058-61-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
4-Stigmasten-3-one	HMDB
b-Sitostenone	Generator
beta-Sitostenone	biospider
laquo deltaraquo 4-Sitosterol-3-one	HMDB
Laquo deltaraquo 4-sitosterol-3-one	HMDB
Sitost-4-en-3-one	HMDB
Sitostenone	HMDB
«DELTA»4-Sitosterol-3-one	biospider
Β-sitostenone	Generator

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.6e-05 g/L	ALOGPS
logP	6.95	ALOGPS
logP	8.41	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.71 m³·mol⁻¹	ChemAxon
Polarizability	52.87 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	Yes	ChemAxon

Chemical Formula

C29H48O

IUPAC name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

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/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24?,25?,26?,27?,28+,29-/m1/s1

InChI Key

RUVUHIUYGJBLGI-AXAJWWPKSA-N

Isomeric SMILES

CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C

Average Molecular Weight

412.6908

Monoisotopic Molecular Weight

412.370516158

Classification

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
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Source:

Biological:

Animal

Plant:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 84.40%; H 11.72%; O 3.88%	DFC
Melting Point	Mp 95-96.5°	DFC
Optical Rotation	[a]D +81.3	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	beta-Sitostenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-3129000000-15ebf2ee5480bfd577c7	Spectrum
Predicted GC-MS	beta-Sitostenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1115900000-b4d381028de9800d2e43	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-7229200000-28c62fdbbd0322f6f3b5	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9045000000-88ed42bed31da02b16cc	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-a3b18c4a22bf0e167d5f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-7c7eb5ad66f7a269c890	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2019000000-9799ee0044320c2ac354	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0013900000-dd3f19a6784ecef0a3a8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0203-9236200000-f893636a370cd6916e85	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9620000000-d480b6411e0b1ddc74b5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-363450e12a0ea926276e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000900000-04f321f2b318172184db	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btd-0029800000-808df1c4b5b606832bba	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

60123241

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33934

CRC / DFC (Dictionary of Food Compounds) ID

HDN90-F:HDN90-F

EAFUS ID

Not Available

Dr. Duke ID

STIGMAST-4-EN-3-ONE|STIGMAST-4-ENE-3-ONE|BETA-SITOSTENONE

BIGG ID

Not Available

KNApSAcK ID

C00029821

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Cardamom	Expected but not quantified	Not Available	DUKE
Corn	Expected but not quantified	Not Available	KNAPSACK
Date	Expected but not quantified	Not Available	DUKE
Soy bean	Expected but not quantified	Not Available	DUKE