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
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
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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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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
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SUB33584
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65036
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allicin
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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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SUBSTANCE RECORD