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MetaCyc Compound Class: a thiol

Superclasses: an organosulfur compound

a thiol compound structure

Child Classes: a disulfide (0) , a perthiol (1) , a polysulfide (0) , a protein disulfide (0) , a protein dithiol (0) , a thioether (3) , an alkyl-thiol (0) , R'C(R)SH (0)

Instances:
(1/2,5,6)-2-(3-azibutylthio)-5,6-epoxy-3-cyclohexen-1-ol ,
3-(methylthio)propanoate ,
cysteamine ,
desacetylmycothiol ,
ethanethiol ,
furfuryl thiol ,
glutathione ,
glutathione amide ,
glutathione amide disulfide ,
glutathione amide perthiol ,
L-dithiothreitol ,
mercaptohistidine ,
methanethiol ,
mycothiol ,
ovothiol ,
thiobenzoate ,
thiocyanate ,
thiophenol ,
trichloromethanethiol

SMILES: S[R]

Unification Links: KEGG:C00145

Reactions known to consume the compound:

glutathione-mediated detoxification II , sulfur volatiles biosynthesis :
a thiol + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a methyl thioether + H+

sulfur oxidation IV (intracellular sulfur) :
a perthiol + a [Rhd protein]-L-cysteine → a thiol + a [Rhd protein] persulfide
intracellular S0n + a thiol → intracellular S0n-1 + a perthiol

thiosulfate disproportionation I (thiol-dependent) :
thiosulfate + 2 a thiol → sulfite + hydrogen sulfide + a disulfide + H+

Not in pathways:
a [sulfatase]-L-cysteine + 2 a thiol + oxygen → a [sulfatase]-3-oxo-L-alanine + hydrogen sulfide + a disulfide + H2O

Reactions known to produce the compound:

glutathione-mediated detoxification I , glutathione-mediated detoxification II :
an L-cysteine-S-conjugate + H2O → a thiol + pyruvate + ammonium

Not in pathways:
a thioglucoside + H2O → a sugar + a thiol

In Reactions of unknown directionality:

Not in pathways:
an L-cysteine-S-conjugate = a thiol + 2-aminoprop-2-enoate + H+
3'-phosphoadenylyl-sulfate + a thiol = an S-alkyl thiosulfate + adenosine 3',5'-bisphosphate

Enzymes activated by a thiol, sorted by the type of activation, are:

Activator (Mechanism unknown) of: α-galactosidase [Burstein71] , acetaldehyde dehydrogenase [Rudolph68, Shone81]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: nitric-oxide synthase , nitric oxide synthase , nitric-oxide synthase


References

Burstein71: Burstein C, Kepes A (1971). "The alpha-galactosidase from Escherichia coli K12." Biochim Biophys Acta 1971;230(1);52-63. PMID: 5543331

Rudolph68: Rudolph FB, Purich DL, Fromm HJ (1968). "Coenzyme A-linked aldehyde dehydrogenase from Escherichia coli. I. Partial purification, properties, and kinetic studies of the enzyme." J Biol Chem 1968;243(21);5539-45. PMID: 4301680

Shone81: Shone CC, Fromm HJ (1981). "Steady-state and pre-steady-state kinetics of coenzyme A linked aldehyde dehydrogenase from Escherichia coli." Biochemistry 1981;20(26);7494-501. PMID: 7034777


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 Thu Sep 3, 2015, biocyc13.