MetaCyc Compound: allylsulfenate

Synonyms: allylsulfenic acid

Superclasses: an organosulfur compoundan S-alkylsulfenate
an organosulfur compound

Two allylsulfenic acid molecules join to form allicin [Shimon07]

Chemical Formula: C3H6OS

Molecular Weight: 90.14 Daltons

Monoisotopic Molecular Weight: 90.0139355047 Daltons

allylsulfenate compound structure


InChI: InChI=1S/C3H6OS/c1-2-3-5-4/h2,4H,1,3H2


Unification Links: ChemSpider:15261538, PubChem:14917355

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 115.316734Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

alliin metabolism :
2 allylsulfenate → allicin + H2O

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

Reactions known to produce the compound:

alliin metabolism :
allicin → thioacrolein + allylsulfenate
alliin → allylsulfenate + 2-aminoprop-2-enoate + H+

In Reactions of unknown directionality:

Not in pathways:
an S-alkylsulfenate + an oxidized unknown electron acceptor = a sulfine + an reduced unknown electron acceptor
an S-alkyl-L-cysteine S-oxide = an S-alkylsulfenate + 2-aminoprop-2-enoate + H+


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

Shimon07: Shimon LJ, Rabinkov A, Shin I, Miron T, Mirelman D, Wilchek M, Frolow F (2007). "Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor." J Mol Biol 366(2);611-25. PMID: 17174334

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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
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