Bovine Metabolome Database: Showing metabocard for beta-Sitosterol (BMDB0062198)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-06-29 22:18:06 UTC

Update Date

2020-05-11 20:56:43 UTC

BMDB ID

BMDB0062198

Secondary Accession Numbers

BMDB62198

Metabolite Identification

Common Name

beta-Sitosterol

Description

beta-Sitosterol, also known as sitosterol or a-phytosterol, 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. Thus, beta-sitosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on beta-Sitosterol.

Structure

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

Synonyms

Value	Source
(-)-beta-Sitosterol	ChEBI
(24R)-Ethylcholest-5-en-3beta-ol	ChEBI
(24R)-Stigmast-5-en-3beta-ol	ChEBI
(3beta)-Stigmast-5-en-3-ol	ChEBI
22,23-Dihydrostigmasterol	ChEBI
24alpha-Ethylcholesterol	ChEBI
alpha-Dihydrofucosterol	ChEBI
Azuprostat	ChEBI
beta-Sitosterin	ChEBI
Cupreol	ChEBI
Nimbosterol	ChEBI
Triastonal	ChEBI
Sitosterol	Kegg
Harzol	Kegg
(-)-b-Sitosterol	Generator
(-)-Β-sitosterol	Generator
(24R)-Ethylcholest-5-en-3b-ol	Generator
(24R)-Ethylcholest-5-en-3β-ol	Generator
(24R)-Stigmast-5-en-3b-ol	Generator
(24R)-Stigmast-5-en-3β-ol	Generator
(3b)-Stigmast-5-en-3-ol	Generator
(3Β)-stigmast-5-en-3-ol	Generator
24a-Ethylcholesterol	Generator
24Α-ethylcholesterol	Generator
a-Dihydrofucosterol	Generator
Α-dihydrofucosterol	Generator
b-Sitosterin	Generator
Β-sitosterin	Generator
b-Sitosterol	Generator
Β-sitosterol	Generator
24-Ethylcholest-5-en-3 beta-ol	HMDB
24-Ethylcholesterol	HMDB
3beta-Sitosterol	HMDB
3beta-Stigmast-5-en-3-ol	HMDB
Clionasterol	HMDB
Sitosterol, (3beta)-isomer	HMDB
22,23-Dihydro-stigmasterol	HMDB
a-Phytosterol	HMDB
alpha-Phytosterol	HMDB
Angelicin	HMDB
beta-Phytosterol	HMDB
Cinchol	HMDB
D5-Stigmasten-3b-ol	HMDB
Delta5-Stigmasten-3b-ol	HMDB
Phytosterol	HMDB
Prostasal	HMDB
Quebrachol	HMDB
Rhamnol	HMDB
Sito-lande	HMDB
Sobatum	HMDB
Stigmast-5-en-3-ol	HMDB
Stigmast-5-en-3b-ol	HMDB
Stigmast-5-en-3beta-ol	HMDB
Stigmast-5-en-3β-ol	HMDB
delta5-Stigmasten-3beta-ol	HMDB
Δ5-stigmasten-3β-ol	HMDB
Α-phytosterol	HMDB
Rhammol	HMDB
Δ5-stigmasten-3beta-ol	HMDB
beta-Sitosterol	ChEBI

Chemical Formula

C₂₉H₅₀O

Average Molecular Weight

414.718

Monoisotopic Molecular Weight

414.38616623

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

83-46-5

SMILES

[H][C@@](CC)(CC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-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
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:27693 )
phytosterols (CHEBI:27693 )
stigmastane (C01753 )
Stigmasterols and C24-ethyl derivatives (C01753 )
Stigmasterols and C24-ethyl derivatives (LMST01040129 )

Ontology

Status

Detected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.27	ALOGPS
logP	7.84	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	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	6	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-054k-3912000000-22f633cd1bdd2ecca960	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0aor-9810000000-ab4d6cb3490b23c5cb70	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-5947700000-fe0573c7669e97c469f5	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2931000000-0d63e91b728deb1446a4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9822000000-2be95863c114e7cd2597	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9601000000-edade780f6cfb8ddc7d1	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-054k-3912000000-22f633cd1bdd2ecca960	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052v-1109000000-2eef6dd56a6c52421610	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-4103900000-a09c1c265657e57bd096	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0002900000-f2b81675160568c483c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05nb-3930100000-897e65b10be8a412585c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-6900000000-b62b8d1bd807fc41256b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0aor-9810000000-fcbfd841778e213b3d3e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-5947700000-4234b723ccdb0e25d290	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0002-2931000000-b2156fbd63c29312b076	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0a4l-9822000000-2be95863c114e7cd2597	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0019500000-b9eddfa8d56747167ada	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-5139100000-42d184a108f9e994dc01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9076000000-54ef98673160128cbacd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-158617c2e43f1a46b58a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-632250471791929b07e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2019000000-717c6229722cf73f3faa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-eda302082c5114b2ab3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-86165feb8e32cd8692ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0001900000-1fc08db7654e3c4918f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4117900000-f005f19377309e9fb82d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06du-9146100000-d28aeb2182048e0912fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9511000000-ff6bd6e1f8902e32555d	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9821000000-0f43ba6def9281d5c86d	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Blood
Fibroblasts
Intestine
Kidney
Liver
Prostate Tissue
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details