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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H48O
Molecular Weight 412.6908
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIGMASTEROL

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

InChIKey=HCXVJBMSMIARIN-PHZDYDNGSA-N
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

HIDE SMILES / InChI

Description

Stigmasterol (also known as Wulzen anti-stiffness factor) is a plant sterol, or phytosterol. Recent investigation discovered that this compound could be new promising anti- Methicillin-resistant Staphylococcus aureus agent.

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis.
1980 Feb
Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography.
1999 Sep 10
Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed.
2002 Sep
Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection.
2003 Jul 15
Natural antimycobacterial metabolites: current status.
2004 Apr
Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative.
2004 Jan
A proteoglycan mediates inductive interaction during plant vascular development.
2004 Jun 24
Use of fecal steroids to infer the sources of fecal indicator bacteria in the Lower Santa Ana River Watershed, California: sewage is unlikely a significant source.
2004 Nov 15
Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake.
2004 Oct
Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L.
2005 Jan
Components and antibacterial activity of the roots of Salvia jaminiana.
2005 Jul
Enteric microbiome metabolites correlate with response to simvastatin treatment.
2011
Relative expression of cholesterol transport-related proteins and inflammation markers through the induction of 7-ketosterol-mediated stress in Caco-2 cells.
2013 Jun
Patents

Patents

JP2000086489A
5
JP2000103727A
1
JP2000119696A
2
JP2000159792A
10
JP2000175643A
2
JP2000178205A
2
JP2000245360A
1
JP2000256120A
1
JP2000300191A
1
JP2000344650A
1
JP2000513730A
3
JP2001002574A
1
JP2001010946A
1
JP2001039849A
3
JP2001048728A
2
JP2001064669A
1
JP2001064671A
1
JP2001089353A
1
JP2001106631A
1
JP2001163764A
1
JP2001224309A
1
JP2002112747A
1
JP2002145722A
1
JP2002171931A
1
JP2002199856A
1
JP2002291442A
1
JP2002326920A
3
JP2002370961A
1
JP2002517418A
2
JP2002535975A
2
JP2002537317A
97
JP2002542177A
1
JP2002542192A
5
JP2002543088A
1
JP2003020495A
1
JP2003104826A
2
JP2003113089A
1
JP2003171310A
1
JP2003235484A
1
JP2003267840A
1
JP2003342121A
1
JP2003500452A
11
JP2003512850A
4
JP2004123608A
5
JP2004143150A
1
JP2004168714A
2
JP2004168715A
2
JP2004168995A
1
JP2004196665A
6
JP2004196666A
4
JP2004256471A
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Time-kill analysis of one Methicillin-resistant Staphylococcus aureus (MRSA) reference strain (ATCC 43300) and three clinical isolates (WM3, BM1 and KJ7) for stigmasterol was first performed to provide the bacteriostatic/bactericidal profile. Then, MRSA ATCC 43300 strain treated by compound was interrogated by next-generation sequencing
Unknown
Name Type Language
STIGMASTEROL
HSDB   MI   WHO-DD  
Common Name English
STIGMASTERIN
Common Name English
STIGMASTA-5,22-DIEN-3.BETA.-OL
Systematic Name English
STIGMASTEROL [MI]
Common Name English
.BETA.-STIGMASTEROL
Common Name English
(3.BETA.,22E)-STIGMASTA-5,22-DIEN-3-OL
Systematic Name English
3.BETA.-HYDROXY-24-ETHYL-.DELTA.(SUP 5,22)-CHOLESTADIENE
Common Name English
STIGMASTEROL (CONSTITUENT OF PYGEUM) [DSC]
Common Name English
NSC-8095
Code English
STIMASTEROL
Common Name English
STIGMASTEROL [HSDB]
Common Name English
.DELTA.5-STIGMASTEROL
Common Name English
WULZEN ANTI-STIFFNESS FACTOR
Common Name English
GUINEA-PIG-ANTI-STIFFNESS FACTOR
Common Name English
STIGMASTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
.DELTA.5,22-STIGMASTADIEN-3.BETA.-OL
Common Name English
Stigmasterol [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 2396 (Number of products:45)
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
NCI_THESAURUS C68437
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
LOINC 74886-3
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
Code System Code Type Description
MERCK INDEX
m10214
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY Merck Index
NSC
8095
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-482-7
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
RXCUI
10079
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
STIGMASTEROL
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
HSDB
7683
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
SMS_ID
100000173041
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
CHEBI
28824
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID801015733
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
PUBCHEM
5280794
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
CAS
83-48-7
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
FDA UNII
99WUK5D0Y8
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
NCI_THESAURUS
C68427
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of STIGMASTEROL
NIH
NCATS
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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