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

[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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Natural antimycobacterial metabolites: current status.
2004 Apr
Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities.
2005 Apr
Components and antibacterial activity of the roots of Salvia jaminiana.
2005 Jul
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005 Oct
Enteric microbiome metabolites correlate with response to simvastatin treatment.
2011
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
PRIVACY ACT
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