SINIGRIN MONOHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16NO9S2.K.H2O
Molecular Weight	415.479
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[K+].OC[C@H]1O[C@@H](S\C(CC=C)=N/OS([O-])(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=IUBVMJHASFBYGW-YEIBXKIESA-M

InChI=1S/C10H17NO9S2.K.H2O/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);;1H2/q;+1;/p-1/b11-6-;;/t5-,7-,8+,9-,10+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	HO
Molecular Weight	17.0073
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C10H17NO9S2
Molecular Weight	359.373
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	K
Molecular Weight	39.0983
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27043505 | https://www.ncbi.nlm.nih.gov/pubmed/25329483 | https://www.ncbi.nlm.nih.gov/pubmed/20889681

Sinigrin is a glucosinolate that is found in plants of the Brassicaceae family. It is enzymatically degraded to allyl isothiocyanate which is responsible for the taste of mustard and horseradish. Allyl isothiocyanate has been identified as having anti-cancer effects; although sinigrin, itself, is not bioactive. Sinigrin has also been shown to have anti-inflammatory activity, antibacterial activity, antifungal activity, antioxidant activity, and wound healing activity.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis regulator Bcl-2 19 Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483	Modulator 828
Cellular tumor antigen p53 20 Target ID: P04637\|\|\|Q16810\|\|\|Q3LRW5\|\|\|Q9NZD0 Gene ID: 7157.0 Gene Symbol: TP53 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483	Modulator 828
CHEMBL3831289: Caspase 3 Target ID: CHEMBL3831289: Caspase Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Bladder cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20889681	Primary	Natural Metabolite	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483	Primary	Natural Metabolite	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27043505 http://www.fasebj.org/content/29/1_Supplement/609.1	Primary	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion.	2010 Dec	20889681
Anti-proliferative activities of sinigrin on carcinogen-induced hepatotoxicity in rats.	2014	25329483

Patents

Sample Use Guides

In Vivo Use Guide

Sprague Dawley rats were induced with carcinogens and treated orally with sinigrin at daily doses of 10 mg/kg, 15 mg/kg and 25 mg/kg for 20 weeks. Rats treated with sinigrin showed significantly less carcinogenic liver damage and improved response to treatment with doxorubicin.

Route of Administration: Oral

In Vitro Use Guide

Human bladder cancer UM-UC-3 cells and rat bladder cancer AY-27 cells were grown for 24 hours and then incubated with sinigrin for 72 hours, with and without myrosinase (0.1 IU/mL). Cell growth and death were monitored to determine (IC50). Pure sinigrin was ineffective but in the presence of myrosinase IC50 values were recorded for each cell line as 13.3 μM (UM-UC-3) and 8.5 μM (AY-27).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:22:02 GMT 2023` Edited by `admin` on `Sat Dec 16 11:22:02 GMT 2023`
Record UNII	2I23137819
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SINIGRIN MONOHYDRATE

Common Name

English

.BETA.-D-GLUCOPYRANOSE, 1-THIO-, 1-(N-(SULFOOXY)-3-BUTENIMIDATE), MONOPOTASSIUM SALT, MONOHYDRATE, (Z)-

Systematic Name

English

SINIGRIN MONOHYDRATE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m9953