MetaCyc Compound: allicin

Synonyms: diallyl thiosulfinate, DADSO, diallyldisulfid-S-oxid, S-Allyl acrylo-1-sulphinothioate, allylthiosulphinic acid allyl ester

Superclasses: an organosulfur compounda dialkyl-thiosulfinate

Allicin is a defense molecule produced by garlic ( Allium sativum with a broad range of biological activities. Allicin is physiologically active in microbial, plant and mammalian cells, due to its ability to participate in redox-reactions with thiol groups in glutathione and proteins.

In a dose-dependent manner allicin can inhibit the proliferation of both bacteria and fungi, and even kill cells, including antibiotic-resistant strains like methicillin-resistant Staphylococcus aureus (MRSA) [Borlinghaus14].

Chemical Formula: C6H10OS2

Molecular Weight: 162.26 Daltons

Monoisotopic Molecular Weight: 162.0173063231 Daltons

allicin compound structure


InChI: InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2


Unification Links: ChEBI:28411, ChemSpider:58548, HMDB:HMDB33963, KEGG:C07600, PubChem:65036

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 118.181206Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

alliin metabolism :
allicin → thioacrolein + allylsulfenate

Reactions known to produce the compound:

alliin metabolism :
2 allylsulfenate → allicin + H2O

Not in pathways:
2 an S-alkylsulfenate → a dialkyl-thiosulfinate + H2O

Revised 05-Dec-2014 by Caspi R, SRI International


Borlinghaus14: Borlinghaus J, Albrecht F, Gruhlke MC, Nwachukwu ID, Slusarenko AJ (2014). "Allicin: chemistry and biological properties." Molecules 19(8);12591-618. PMID: 25153873

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Thu May 5, 2016, biocyc14.