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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
Molecular Formula C29H48O
Molecular Weight 412.6908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 1
Optical Activity UNSPECIFIED

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
Rapid microanalysis of cholesterol in bile and serum by gas chromatography.
1975 Jan-Feb
Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis.
1980 Feb
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography.
1999 Sep 10
The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1.
2001 Mar
Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures.
2002 Jan
Antitubercular constituents from the hexane fraction of Morinda citrifolia Linn. (Rubiaceae).
2002 Nov
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
A proteoglycan mediates inductive interaction during plant vascular development.
2004 Jun 24
Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake.
2004 Oct
Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities.
2005 Apr
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005 Oct
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:48 GMT 2023
Record UNII
99WUK5D0Y8
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
EUPATORIUM PERFOLIATUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COMFREY LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
PLANTAGO OVATA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
COMFREY ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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