Cannabis Compound Database: Showing Compound Card for Stigmasterol (CDB006176)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Created at

2020-03-18 23:22:36 UTC

Updated at

2020-12-07 19:06:59 UTC

CannabisDB ID

CDB006176

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Stigmasterol

Description

Stigmasterol, also known as poriferasterol or 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. Stigmasterol is a phytosterol, meaning it is steroid derived from plants. ,It is very hydrophobic, practically insoluble in water, and relatively neutral. Stigmasterol is among the most abundant of plant sterols with its major function being to maintain the structure and physiology of cell membranes. It is found in plant fats or oils associated with various vegetables, legumes, nuts, and seeds such as¬†soybean,¬†calabar bean, rape seed and various herbs. Stigmasterol is also a constituent of unpasteurized milk. Pasteurization is known to inactivate stigmasterol. Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Consumption of 2 grams per day of plant sterols is associated with a reduction in blood LDL cholesterol of 8-10% (PMID: 29267628 ). As the typical western diet contains only about 300 mg/day of phytosterols, foods enriched with phytosterols are usually used to achieve the recommended intake (PMID: 29267628 ). The mechanism behind phytosterols lowering cholesterol involves the inhibition of the incorporation of cholesterol into micelles in the gastrointestinal tract, which decreases the overall amount of cholesterol absorbed. This may in turn help to control body total plasma cholesterol levels, as well as modify HDL, LDL and TAG levels in blood. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people wishing to lower their cholesterol levels. More recently, stigmasterol has been identified as a potent and independent risk factor for cardiovascular disease. Accumulation of stigmasterol leads to left ventricle dysfunction, cardiac interstitial fibrosis and macrophage infiltration without atherosclerosis (PMID: 30675518 ). Stigmasterol has been found to be associated with phytosterolemia, a disease characterized by elevated levels of dietary plant sterols in the blood. (PMID: 30675518 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,22E)-Stigmasta-5,22-dien-3-ol	ChEBI
5,22-Cholestadien-24-ethyl-3beta-ol	ChEBI
beta-Stigmasterol	ChEBI
Phytosterol	ChEBI
Poriferasterol	ChEBI
Stigmasta-5,22-dien-3beta-ol	ChEBI
(3b,22E)-Stigmasta-5,22-dien-3-ol	Generator
(3β,22E)-Stigmasta-5,22-dien-3-ol	Generator
5,22-Cholestadien-24-ethyl-3b-ol	Generator
5,22-Cholestadien-24-ethyl-3β-ol	Generator
b-Stigmasterol	Generator
β-Stigmasterol	Generator
Stigmasta-5,22-dien-3b-ol	Generator
Stigmasta-5,22-dien-3β-ol	Generator
(24S)-5,22-Stigmastadien-3b-ol	HMDB
17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
Stigmasta-5,22-dien-3-b-ol	HMDB
Stigmasta-5,22-dien-3-beta-ol	HMDB
Stigmasterin	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3beta-ol	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3β-ol	HMDB
(24S)-5,22-Stigmastadien-3beta-ol	HMDB
(24S)-5,22-Stigmastadien-3β-ol	HMDB
(24S)-Stigmast-5,22-dien-3beta-ol	HMDB
(24S)-Stigmast-5,22-dien-3β-ol	HMDB
24-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24-Ethyl-5,22-cholestadien-3β-ol	HMDB
24beta-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24β-Ethyl-5,22-cholestadien-3β-ol	HMDB
Stigmasta-5,22(E)-dien-3beta-ol	HMDB
Stigmasta-5,22(E)-dien-3β-ol	HMDB
Stigmasterol	HMDB
delta5,22-Stigmastadien-3beta-ol	HMDB
delta5-Stigmasterol	HMDB
Δ5,22-Stigmastadien-3β-ol	HMDB
Δ5-Stigmasterol	HMDB

Chemical Formula

C₂₉H₄₈O

Average Molecular Weight

412.7

Monoisotopic Molecular Weight

412.3705

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-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,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

83-48-7

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

HCXVJBMSMIARIN-PHZDYDNGSA-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:28824 )
phytosterols (CHEBI:28824 )
stigmastane (C05442 )
Stigmasterols and C24-ethyl derivatives (C05442 )
Stigmastane and derivatives (C05442 )
Stigmasterols and C24-ethyl derivatives (LMST01040123 )

Ontology

Physiological effect

Health effect:

Health condition:

Sitosterolemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Role

Biological role:

Molecular messenger:

Industrial application:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	490.4 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.95	ALOGPS
logP	7.48	ChemAxon
logS	-7.2	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	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	53.55 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a59-8920000000-c7d02c3957677fae28be	2015-03-01	View Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a4i-3941000000-4b20188a87c1dadeae49	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9720000000-02211a4df6ec5c313295	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-053r-7941000000-7983b2cb8a74cfda7530	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9731000000-168578ccead65322e450	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a4i-3941000000-4b20188a87c1dadeae49	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9720000000-02211a4df6ec5c313295	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-053r-7941000000-7983b2cb8a74cfda7530	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9731000000-168578ccead65322e450	Spectrum
Predicted GC-MS	Stigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001j-1109000000-be897608aaeab74e5d13	Spectrum
Predicted GC-MS	Stigmasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0avl-2102900000-564b610342ad160ee822	Spectrum
Predicted GC-MS	Stigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Stigmasterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03di-0000900000-f7738a3fcdee344f82c9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-07cs-9400200000-959314bea26c5acd8301	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a59-7900000000-ce066e558ecbe29afea8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0a4i-3941000000-f854893a9352ff766734	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a59-9720000000-5a3d902c3cd2af078da3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-053r-7941000000-6c5c63e8c487f86b353b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a59-9731000000-32a70fa14fd448314caa	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2019500000-3495ed3a1955cc77528a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9128100000-3c3b91bb2d698a88f9db	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-8197000000-a80e8fcc32cd4a2dfefe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-322cae85ce921a9ef9e2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-d25be97b0cfa1b9bed79	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-2019000000-3b119d03e184f575cdc4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-2219400000-9acb072e76ff1b8f2e48	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-7259000000-a7f52c0e28b61ef2a3ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9320000000-8a54eac3182f86b7095b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-363450e12a0ea926276e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-fe3ab0b12c2d51198ed0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1001900000-43dce6fa5af31f5d7958	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Delta(24)-sterol reductase	DHCR24	1p32.3	Q15392	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000937

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Stigmasterol

METLIN ID

168

PubChem Compound

5280794

PDB ID

Not Available

ChEBI ID

28824

References

General References

Cabral CE, Klein MRST: Phytosterols in the Treatment of Hypercholesterolemia and Prevention of Cardiovascular Diseases. Arq Bras Cardiol. 2017 Nov;109(5):475-482. doi: 10.5935/abc.20170158. [PubMed:29267628 ]
Tao C, Shkumatov AA, Alexander ST, Ason BL, Zhou M: Stigmasterol accumulation causes cardiac injury and promotes mortality. Commun Biol. 2019 Jan 16;2:20. doi: 10.1038/s42003-018-0245-x. eCollection 2019. [PubMed:30675518 ]

Enzymes

Enzyme Details

1. Delta(24)-sterol reductase

General function:: Energy production and conversion
Specific function:: Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:: DHCR24
Uniprot ID:: Q15392
Molecular weight:: 60100.805

Showing Compound Card for Stigmasterol (CDB006176)

Structure for CDB006176 (Stigmasterol)

Enzymes