SITOGLUSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H60O6
Molecular Weight	576.8473
Optical Activity	UNSPECIFIED
Defined Stereocenters	14 / 14
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]5([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](C)CC[C@@H](CC)C(C)C

InChI

InChIKey=NPJICTMALKLTFW-OFUAXYCQSA-N

InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24+,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C35H60O6
Molecular Weight	576.8473
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	14 / 14
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26209138 | https://www.ncbi.nlm.nih.gov/pubmed/28611451 | https://www.ncbi.nlm.nih.gov/pubmed/24333794 | https://www.ncbi.nlm.nih.gov/pubmed/25864625

SITOGLUSIDE (Daucosterol) inhibits cancer cell proliferation by inducing autophagy through reactive oxygen species-dependent manner. It also perturbs cell cycle and induces apoptotic cell death in A549 cells. Daucosterol has being shown to promote the proliferation of neural stem cells. Daucosterol also protects neurons against oxygen-glucose deprivation/reperfusion-mediated injury by activating IGF1 signaling pathway. Daucosterol could be potentially developed as a medicine for ischemic stroke treatment.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28611451 \| https://www.banglajol.info/index.php/BJP/article/view/25754	Activator 1430
BGC-823 2 Target ID: CHEMBL614526 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26209138	Inhibitor 8297	3.13 µM [IC50]
Signaling by Type 1 Insulin-like Growth Factor 1 Receptor (IGF1R) 1 Target ID: WP2677 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25864625	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26209138 https://www.ncbi.nlm.nih.gov/pubmed/28611451 https://www.banglajol.info/index.php/BJP/article/view/25754	Primary		Preclinical	Unknown Approved Use Unknown
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25864625	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synergistic versus antagonistic actions of glutamate and glutathione: the role of excitotoxicity and oxidative stress in neuronal disease.	2002 Mar	11990449
HIV-1 integrase inhibitory substances from Coleus parvifolius.	2003 Mar	12672152
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.	2005 Oct	16261518

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.5mg/kg daucosterol significantly inhibit the H22 tumor growth in vivo (0.71±0.29 g vs 1.51±0.23 g in control grroup). Moreover, 2.5mg/kg daucosterol treatment further lowered the tumor weight to 0.46±0.28g (p<0.01).

Route of Administration: Oral

In Vitro Use Guide

Daucosterol inhibited the proliferation of cancer cells in a dose-dependent manner. IC50 value was calculated as 19.96 uM for MCG803, 3.13 uM for BGC823, 24.19 uM for AGS and 16.95 uM for MCF-7, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:45:01 GMT 2023` Edited by `admin` on `Sat Dec 16 16:45:01 GMT 2023`
Record UNII	U45VN859W3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SITOGLUSIDE

Official Name

English

WA 184

Code

English

AW 10

Code

English

CORIANDRINOL

Common Name

English

.BETA.-SITOSTEROL-.BETA.-D-GLUCOSIDE

Common Name

English

SITOSTEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

NSC-165962

Code

English

AW-10

Code

English

DAUCOSTERIN

Common Name

English

BSSG

Code

English

BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE) [DSC]

Common Name

English

.BETA.-SITOSTEROL-GLUCOSIDE

Common Name

English

ALEXANDRIN

Common Name

English

SITOGLUSIDE [USAN]

Common Name

English

LYONISIDE

Common Name

English

BSS-G

Code

English

.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.)-STIGMAST-5-EN-3-YL

Common Name

English

3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)STIGMAST-5-ENE

Common Name

English

DAUCOSTEROL

Common Name

English

EU-4906

Code

English

WA-184

Code

English

DAUCOSTERINE

Common Name

English

sitogluside [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308