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
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
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 |
---|---|---|---|
Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483 |
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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 |
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Target ID: CHEMBL3831289: Caspase Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25329483
Curator's Comment: referenced study was conducted in rat
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20889681
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).
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD