SINIGRIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16NO9S2.K
Molecular Weight	397.464
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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=QKFAFSGJTMHRRY-FVDOMRANSA-M

InChI=1S/C10H17NO9S2.K/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);/q;+1/p-1/b11-6-;/t5-,7-,8+,9-,10+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C10H16NO9S2
Molecular Weight	358.365
Charge	-1
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
Sinigrin and Its Therapeutic Benefits.	2016 Mar 29	27043505

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 `Fri Dec 15 19:51:48 GMT 2023` Edited by `admin` on `Fri Dec 15 19:51:48 GMT 2023`
Record UNII	50UM64RMBJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SINIGRIN

Common Name

English

SINIGROSIDE

Common Name

English

GLUCOPYRANOSE, 1-THIO-, 1-(3-BUTENOHYDROXIMATE) NO-(HYDROGEN SULFATE), MONOPOTASSIUM SALT, .BETA.-D-

Systematic Name

English

GLUCOPYRANOSE, 1-THIO-, 1-(3-BUTENOATE), OXIME, O-SULFATE, POTASSIUM SALT, .BETA.-D-

Systematic Name

English

NSC-90774

Code

English

1-THIO-.BETA.-D-GLUCOPYRANOSE 1-(N-(SULFOOXY)-3-BUTENIMIDATE) POTASSIUM SALT (1:1)

Common Name

English

MYRONATE POTASSIUM

Common Name

English

SINIGRINE

Common Name

English

POTASSIUM MYRONATE

Common Name

English

SINIGRIN [MI]

Common Name

English

.BETA.-D-GLUCOPYRANOSE, 1-THIO-, 1-(N-(SULFOOXY)-3-BUTENIMIDATE), POTASSIUM SALT (1:1)

Systematic Name

English

NSC-407279

Code

English

Code System Code Type Description

NSC

90774