Details
Stereochemistry | RACEMIC |
Molecular Formula | C6H10OS2 |
Molecular Weight | 162.273 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][S+](CC=C)SCC=C
InChI
InChIKey=JDLKFOPOAOFWQN-UHFFFAOYSA-N
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
Molecular Formula | C6H10OS2 |
Molecular Weight | 162.273 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Allicin (diallylthiosulfinate) is a defence molecule from garlic (Allium sativum L.) with a broad range of biological activities. Allicin is produced upon tissue damage from the non-proteinogenic amino acid alliin (S-allylcysteine sulfoxide) in a reaction that is catalyzed by the enzyme alliinase. Allicin is known to be hydrophobic and can be readily absorbed through the cell membrane without inducing any damage to the phospholipid bilayer and then rapidly metabolized to exert pharmacological effects. The majority of allicin's effects are believed to be mediated via redox-dependent mechanisms. Allicin is physiologically active in microbial, plant and mammalian cells. In a dose-dependent manner allicin can inhibit the proliferation of both bacteria and fungi or kill cells outright, including antibiotic-resistant strains like methicillin-resistant Staphylococcus aureus (MRSA). In plants allicin inhibits seed germination and attenuates root-development. Furthermore, in mammalian cell lines, including cancer cells, allicin induces cell-death and inhibits cell proliferation. Allicin was found to provide cardio-protective effects by inducing vasorelaxation and alleviating various pathological conditions of CVD, including cardiac hypertrophy, angiogenesis, platelet aggregation, hyperlipidemia and hyperglycemia. Allicin was also discovered to further protect the cardiovascular system by enhancing the antioxidant status by lowering the level of reactive oxygen species and stimulating the production of glutathione.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1. | 2007 Aug 14 |
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Comparison between efficacy of allicin and fluconazole against Candida albicans in vitro and in a systemic candidiasis mouse model. | 2011 Feb |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:14:17 GMT 2023
by
admin
on
Fri Dec 15 18:14:17 GMT 2023
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Record UNII |
3C39BY17Y6
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68520
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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DSLD |
2437 (Number of products:54)
Created by
admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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Code System | Code | Type | Description | ||
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3C39BY17Y6
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28411
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DTXSID6043707
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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C68521
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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C006452
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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m1523
Created by
admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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PRIMARY | Merck Index | ||
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208-727-7
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DB11780
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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539-86-6
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100000127530
Created by
admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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ALLICIN
Created by
admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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SUB33584
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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65036
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admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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allicin
Created by
admin on Fri Dec 15 18:14:17 GMT 2023 , Edited by admin on Fri Dec 15 18:14:17 GMT 2023
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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