AFCDB: alpha1-Sitosterol (FDB001304)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:55 UTC

Update date

2019-11-26 02:56:16 UTC

Primary ID

FDB001304

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha1-Sitosterol

Description

(3beta,4beta,5alpha,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol 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 small amount of articles have been published on (3beta,4beta,5alpha,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol.

CAS Number

474-40-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.6e-05 g/L	ALOGPS
logP	7.85	ALOGPS
logP	7.8	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-1.1	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	135.09 m³·mol⁻¹	ChemAxon
Polarizability	54 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

Chemical Formula

C30H50O

IUPAC name

2,6,15-trimethyl-14-[(5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

InChI Identifier

InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8+

InChI Key

LPZCCMIISIBREI-GZIVZEMBSA-N

Isomeric SMILES

C\C=C(/CCC(C)C1CCC2C3=CCC4C(C)C(O)CCC4(C)C3CCC12C)C(C)C

Average Molecular Weight

426.7174

Monoisotopic Molecular Weight

426.386166222

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
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

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 84.44%; H 11.81%; O 3.75%	DFC
Melting Point	Mp 162-164°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +24 (c, 1 in CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(3b,4b,5a,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ot-1119300000-0bb147a9d879760ae7b7	Spectrum
Predicted GC-MS	(3b,4b,5a,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-2102900000-ed1623cf1eec3edd07fe	Spectrum
Predicted GC-MS	(3b,4b,5a,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3b,4b,5a,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol, 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	splash10-0a6r-0012900000-cde59be93f1463ff00e3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06tb-5239300000-95113b4ddb77ad408faf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pk-8079100000-346450ad4e87290a27ca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-2059eb8c355176c1ed29	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0001900000-9787c3c5e6e68ec281e1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4009600000-8a3e35d1a4792d51fe3d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0009000000-79df37db80711c3d6145	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-9126200000-e3a6cfd791047f04ace2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ce9-9531000000-91266e74d0b6d75d2de4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-590c9e4adfdd12b64d93	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-d780834f52f781580677	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0adl-0004900000-8fab8882c6e870f31bbf	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

9548595

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HDN92-H:BZH80-I

EAFUS ID

Not Available

Dr. Duke ID

24-ETHYLIDENE-LOPHENOL|CITROSTADIENIOL|CITROSTADIENOL

BIGG ID

Not Available

KNApSAcK ID

C00007321

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

alpha1-Sitosterol (FDB001304)

Structure for FDB001304 (alpha1-Sitosterol)