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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H48O
Molecular Weight 412.6919
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIGMASTEROL

SMILES

CC[C@]([H])(/C(/[H])=C(\[H])/[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O)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 412.6919
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
109281
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
Synthesis and bioactivity evaluation of brassinosteroid analogs.
2000 Jun
Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection.
2003 Jul 15
Natural antimycobacterial metabolites: current status.
2004 Apr
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
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005 Oct
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
8
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
82
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
5
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 Sat Jun 26 12:09:30 UTC 2021
Edited
by admin
on Sat Jun 26 12:09:30 UTC 2021
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
STIGMASTEROL [WHO-DD]
Common Name English
.DELTA.5,22-STIGMASTADIEN-3.BETA.-OL
Common Name English
Classification Tree Code System Code
DSLD 2396 (Number of products:45)
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
NCI_THESAURUS C68437
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
LOINC 74886-3
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
Code System Code Type Description
MERCK INDEX
M10214
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
201-482-7
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
RXCUI
10079
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
STIGMASTEROL
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
HSDB
7683
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
PUBCHEM
5280794
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
CAS
83-48-7
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
FDA UNII
99WUK5D0Y8
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
PRIMARY
NCI_THESAURUS
C68427
Created by admin on Sat Jun 26 12:09:30 UTC 2021 , Edited by admin on Sat Jun 26 12:09:30 UTC 2021
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
COMFREY LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COMFREY ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
PLANTAGO OVATA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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