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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Effects of an allicin-based product on cryptosporidiosis in neonatal calves. | 1998 Apr 1 |
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Quantitative determination of allicin in garlic: supercritical fluid extraction and standard addition of alliin. | 2004 Feb 25 |
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In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity. | 2004 Jul-Aug |
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Pungent products from garlic activate the sensory ion channel TRPA1. | 2005 Aug 23 |
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The pungency of garlic: activation of TRPA1 and TRPV1 in response to allicin. | 2005 May 24 |
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Contractile effect of TRPA1 receptor agonists in the isolated mouse intestine. | 2007 Dec 8 |
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Induction of total insensitivity to capsaicin and hypersensitivity to garlic extract in human by decreased expression of TRPV1. | 2007 Jan 10 |
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In vitro investigation of antifungal activity of allicin alone and in combination with azoles against Candida species. | 2010 Apr |
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Allicin alleviates inflammation of trinitrobenzenesulfonic acid-induced rats and suppresses P38 and JNK pathways in Caco-2 cells. | 2015 |
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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DSLD |
2437 (Number of products:54)
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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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Code System | Code | Type | Description | ||
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3C39BY17Y6
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28411
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DTXSID6043707
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C68521
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C006452
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m1523
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208-727-7
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DB11780
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539-86-6
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100000127530
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ALLICIN
Created by
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SUB33584
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65036
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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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