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MetaCyc Compound: allicin

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

Superclasses: an organosulfur compound a dialkyl-thiosulfinate

Summary:
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

SMILES: C=CCSS(CC=C)=O

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

InChIKey: InChIKey=JDLKFOPOAOFWQN-UHFFFAOYSA-N

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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 118.181206 Inferred 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

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


References

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."


Report Errors or Provide Feedback
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 SRI International Pathway Tools version 19.0 on Mon Apr 20, 2015, BIOCYC13A.