U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

CC[C@H](\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)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
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Relative expression of cholesterol transport-related proteins and inflammation markers through the induction of 7-ketosterol-mediated stress in Caco-2 cells.
2013-06
Enteric microbiome metabolites correlate with response to simvastatin treatment.
2011
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005-10
Components and antibacterial activity of the roots of Salvia jaminiana.
2005-07
Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities.
2005-04
Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L.
2005-01
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.
2004-11-15
Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake.
2004-10
A proteoglycan mediates inductive interaction during plant vascular development.
2004-06-24
Natural antimycobacterial metabolites: current status.
2004-04
Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative.
2004-01
Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection.
2003-07-15
Antitubercular constituents from the hexane fraction of Morinda citrifolia Linn. (Rubiaceae).
2002-11
Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed.
2002-09
Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures.
2002-01
The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1.
2001-03
Synthesis and bioactivity evaluation of brassinosteroid analogs.
2000-06
Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography.
1999-09-10
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991-01-01
Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis.
1980-02
Rapid microanalysis of cholesterol in bile and serum by gas chromatography.
1975-01-01
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 Mon Mar 31 17:46:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:18 GMT 2025
Record UNII
99WUK5D0Y8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STIGMASTEROL
HSDB   MI   WHO-DD  
Common Name English
NSC-8095
Preferred 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
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 Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
NCI_THESAURUS C68437
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
LOINC 74886-3
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
Code System Code Type Description
MERCK INDEX
m10214
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY Merck Index
NSC
8095
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-482-7
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
RXCUI
10079
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
STIGMASTEROL
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
HSDB
7683
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
SMS_ID
100000173041
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
CHEBI
28824
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID801015733
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
PUBCHEM
5280794
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
CAS
83-48-7
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
FDA UNII
99WUK5D0Y8
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
PRIMARY
NCI_THESAURUS
C68427
Created by admin on Mon Mar 31 17:46:18 GMT 2025 , Edited by admin on Mon Mar 31 17:46:18 GMT 2025
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
PLANTAGO OVATA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
COMFREY LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
COMFREY ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966