Information on EC 2.5.1.18 - glutathione transferase and Organism(s) Homo sapiens

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
2.5.1.18
-
RECOMMENDED NAME
GeneOntology No.
glutathione transferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
RX + glutathione = HX + R-S-glutathione
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aryl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
4-hydroxy-2-nonenal detoxification
-
-
camalexin biosynthesis
-
-
gliotoxin biosynthesis
-
-
glutathione-mediated detoxification I
-
-
glutathione-mediated detoxification II
-
-
indole glucosinolate activation (intact plant cell)
-
-
pentachlorophenol degradation
-
-
glutathione metabolism
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Glutathione metabolism
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Metabolism of xenobiotics by cytochrome P450
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Drug metabolism - cytochrome P450
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Drug metabolism - other enzymes
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SYSTEMATIC NAME
IUBMB Comments
RX:glutathione R-transferase
A group of enzymes of broad specificity. R may be an aliphatic, aromatic or heterocyclic group; X may be a sulfate, nitrile or halide group. Also catalyses the addition of aliphatic epoxides and arene oxides to glutathione, the reduction of polyol nitrate by glutathione to polyol and nitrile, certain isomerization reactions and disulfide interchange.
CAS REGISTRY NUMBER
COMMENTARY hide
50812-37-8
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
a single SNP causing an I71L substitution in African subjects causes diminished activity with several substrates including CDNB and 7-chloro-4-nitrobenz-2-oxa-1,3-diazole as a result of an elevation in its Km for GSH, but the specific activity towards DELTA5-androsten-3,17-dione and the Km GSH of the L71 variant are not changed; associations between GSTO1 polymorphisms and vascular dementia and stroke. A236V polymorphism: the V236 variant protein has low specific activity with a range of substrates and shows marked heat instability. It seems highly likely that this substitution leads to GSTO1-1 deficiency in homozygotes. E155 deletion causes a significant folding defectthat may explain the deficiency associated with this deletion. The V236 variant protein has low specific activity with a range of substrates and shows marked heat instability; differences in the catalytic activity of the V105 and I105 variants to carcinogenic diolepoxides may underlie the associations between these alleles and cancer susceptibility; GSTM1-1 deficiency contributes significantly to survival after chemotherapy for childhood leukemia; natural mutations D43N, T65M and T104P, and a frame shift mutation at G412 cause GSTT1-1 deficiency; the GSTT12B allele results from the relatively rare T104P substitution in Scandinavian individuals, and appears to destabilize the protein and result in GSTT1-1 deficiency. The relatively common deletion of the GSTT2b pseudogene is associated with an altered risk of esophageal squamous cell carcinoma; the GSTZ1-A protein has relatively high activity with (±)-2-bromo-3-(4-nitrophenyl)propanoic acid but it has low isomerase activity with its natural substrate maleylacetoacetate; two rare intronic variants (IVS2+11A>C and IVS3+13T>C) are reported, the intron-2 SNP is significantly transmitted to asthma-affected children
metabolism
-
glutathione S-transferase P1-1 is one of the most important members of phase II detoxification enzyme family which catalyzes the conjugation of glutathione with broad substrates such as chemotherapeutic agents
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-2-bromo-3-(4-nitrophenyl)propanoic acid + glutathione
2-(glutathion-S-yl)-3-(4-nitrophenyl)propanoic acid + HBr
show the reaction diagram
-
-
-
-
?
(13S,9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid + GSH
?
show the reaction diagram
(15S,5Z,8Z,10E,14Z)-15-hydroperoxyeicosa-5,8,10,14-tetraenoic acid + GSH
?
show the reaction diagram
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid + GSH
?
show the reaction diagram
(9S,10E,12E)-9-hydroperoxyoctadeca-10,12-dienoic acid + GSH
?
show the reaction diagram
1,2-dichloro-4-nitrobenzene + GSH
?
show the reaction diagram
-
-
-
-
?
1,2-epoxy-3-(4-nitrophenoxy)-propane + glutathione
?
show the reaction diagram
-
-
-
-
?
1,2-epoxy-3-(p-nitrophenoxy)propane + GSH
?
show the reaction diagram
-
-
-
-
?
1,3,5-trinitrobenzene + glutathione
S-(2,4,6-trinitrocyclohexa-2,5-dien-1-yl)glutathione
show the reaction diagram
an anionic sigma-complex is formed between GSH and 1,3,5-trinitrobenzene and is stabilized by Arg15. The trinitrocyclohexadienate moiety of the sigma-complex binds the H-site where the catalytic residue, Tyr9, was identified to hydrogen bond to an o-nitro group of the sigma-complex
-
-
?
1,3-bis-(2-chloroethyl)-1-nitrosourea + glutathione
?
show the reaction diagram
-
-
-
-
?
1-chloro-2,3-dinitrobenzene + GSH
?
show the reaction diagram
-
-
-
-
?
1-chloro-2,3-dinitrobenzene + GSH
S-(2,3-dinitrophenyl)glutathione + HCl
show the reaction diagram
-
-
-
-
?
1-chloro-2,4-dinitrobenzene + glutathione
2,4-dinitrobenzyl-glutathione + HCl
show the reaction diagram
1-chloro-2,4-dinitrobenzene + glutathione
?
show the reaction diagram
-
-
-
-
?
1-chloro-2,4-dinitrobenzene + glutathione
S-(2,4-dinitrophenyl)glutathione + HCl
show the reaction diagram
1-methyl-4-nitro-5-[(4-nitrophenyl)thio]-1H-imidazole + glutathione
?
show the reaction diagram
-
-
-
-
?
4-hydroxy-2-nonenal + glutathione
?
show the reaction diagram
-
-
-
-
?
4-hydroxy-2-nonenal + GSH
?
show the reaction diagram
-
-
-
-
?
4-hydroxynonenal + GSH
?
show the reaction diagram
-
10% of the activity with 1-chloro-2,3-dinitrobenzene
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-
?
4-nitrobenzyl chloride + glutathione
?
show the reaction diagram
-
-
-
-
?
4-nitrophenethyl bromide + glutathione
?
show the reaction diagram
-
-
-
-
?
4-nitrophenylacetate + glutathione
?
show the reaction diagram
-
-
-
-
?
4-[[(3,4-dinitrophenyl)carbonyl]amino]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid + glutathione
?
show the reaction diagram
-
-
-
-
?
5-[[(3,4-dinitrophenyl)carbonyl]amino]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid + glutathione
?
show the reaction diagram
-
-
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?
7-chloro-4-nitrobenzo-2-oxa-1,3-diazole + glutathione
?
show the reaction diagram
-
-
-
?
7-chloro-4-nitrobenzo-2-oxa-1,3-diazole + GSH
?
show the reaction diagram
-
80% of the activity with 1-chloro-2,3-dinitrobenzene
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-
?
allyl isothiocyanate + glutathione
?
show the reaction diagram
-
-
-
-
?
aminochrome + glutathione
?
show the reaction diagram
-
-
-
-
?
androstenedione + glutathione
?
show the reaction diagram
-
-
-
-
?
azathioprine + glutathione
?
show the reaction diagram
-
aromatic substitution. Wild-type hGST M2-2 has modest activity with azathioprine, but mutant C87A/C115A/C174A/M212C displays no detectable activity. The azathioprine activity of wild-type hGST M2-2 can be enhanced 30fold by two point mutations of other residues in the active site
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-
?
benzyl isothiocyanate + glutathione
?
show the reaction diagram
-
-
-
-
?
brostallicin + glutathione
glutathionyl-brostallicin
show the reaction diagram
butyl nitrite + glutathione
?
show the reaction diagram
-
-
-
-
?
chlorofluoroacetic acid + glutathione
?
show the reaction diagram
-
-
-
-
?
cumene hydroperoxide + glutathione
?
show the reaction diagram
-
-
-
-
?
cumene hydroperoxide + GSH
?
show the reaction diagram
dichloroacetic acid + glutathione
?
show the reaction diagram
-
-
-
-
?
ethacrynic acid + glutathione
?
show the reaction diagram
glutathione + (R)-styrene-7,8-oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + (R,R)-1-phenylpropylene oxide
?
show the reaction diagram
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-
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-
?
glutathione + (R,R)-trans-stilbene oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + (S)-styrene-7,8-oxide
?
show the reaction diagram
-
-
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?
glutathione + (S,S)-1-phenylpropylene oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + (S,S)-trans-stilbene oxide
?
show the reaction diagram
-
-
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-
?
glutathione + 1,2-dichloro-4-nitrobenzene
?
show the reaction diagram
-
-
-
-
?
glutathione + 1,2-diiodoethane
?
show the reaction diagram
-
best substrate
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?
glutathione + 1,2-epoxy-3-(4-nitro-phenoxy)propane
?
show the reaction diagram
-
best substrate for the wild-type GST T1-1 and mutant W234K
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-
?
glutathione + 1,2-epoxy-3-(p-nitrophenoxy)propane
?
show the reaction diagram
-
-
-
?
glutathione + 1,4-diiodobutane
?
show the reaction diagram
-
-
-
-
?
glutathione + 1,6-diiodohexane
?
show the reaction diagram
-
-
-
-
?
glutathione + 1,8-diiodooctane
?
show the reaction diagram
-
-
-
-
?
glutathione + 1-chloro-2,4-dinitrobenzene
chloride + 2,4-dinitrophenyl-glutathione
show the reaction diagram
glutathione + 1-chloro-2,4-dinitrobenzene
S-(2,4-dinitrophenyl)glutathione + HCl
show the reaction diagram
glutathione + 1-chloro-2,4-dinitrobenzene
S-2,4-dinitrophenylglutathione + HCl
show the reaction diagram
glutathione + 1-fluoro-2,4-dinitrobenzene
?
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodo-3-phenylpropane
iodide + 3-phenylpropyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodobutane
iodide + butyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodoethane
iodide + ethylglutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodoheptane
iodide + heptyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodohexane
?
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodohexane
iodide + hexyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodomethane
iodide + methylglutathione
show the reaction diagram
-
best substrate of GST T1-1 mutant W234R
-
-
?
glutathione + 1-iodooctane
iodide + octyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodopentane
iodide + pentyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-iodopropane
iodide + propyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 1-menaphthyl sulfate
?
show the reaction diagram
-
-
-
-
?
glutathione + 1-methyl-4-nitro-5-(4-nitrophenylthio)-1H-imidazole
?
show the reaction diagram
-
-
-
?
glutathione + 2-hydroxyethyl disulfide
?
show the reaction diagram
isozyme GSTO2, low activity
-
-
?
glutathione + 2-methyl-4-nitrobenzyl alcohol
?
show the reaction diagram
-
-
-
-
?
glutathione + 3,4-dichloro-1-nitrobenzene
?
show the reaction diagram
-
-
-
-
?
glutathione + 3,4-dinitrobenzanilide
?
show the reaction diagram
-
-
-
-
?
glutathione + 3-iodopropylbenzene
?
show the reaction diagram
-
-
-
-
?
glutathione + 4-chloro-3-nitroacetophenone
?
show the reaction diagram
-
-
-
-
?
glutathione + 4-chloro-3-nitrobenzophenone
?
show the reaction diagram
-
-
-
-
?
glutathione + 4-fluoro-3-nitrobenzanilide
?
show the reaction diagram
-
-
-
-
?
glutathione + 4-nitrobenzyl chloride
?
show the reaction diagram
-
-
-
-
?
glutathione + 4-nitrobenzyl chloride
chloride + 4-nitrobenzyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 4-nitrobenzyl chloride
S-(2,4-dinitrophenyl)glutathione + HCl
show the reaction diagram
-
-
-
?
glutathione + 4-nitrophenethyl bromide
bromide + 4-nitrophenethyl-glutathione
show the reaction diagram
-
-
-
-
?
glutathione + 7-amino-4-chloromethyl coumarin
?
show the reaction diagram
-
-
-
?
glutathione + 7-chloro-4-nitrobenz-2-oxa-1,3-diazole
?
show the reaction diagram
-
-
-
-
?
glutathione + 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole
?
show the reaction diagram
-
poor substrate
-
-
?
glutathione + acetochlor
?
show the reaction diagram
-
-
-
-
?
glutathione + acrolein
?
show the reaction diagram
-
-
-
-
?
glutathione + adenine propenal
?
show the reaction diagram
-
-
-
-
?
glutathione + alachlor
?
show the reaction diagram
-
-
-
-
?
glutathione + atrazine
?
show the reaction diagram
-
high specific activity
-
-
?
glutathione + azathioprine
6-mercaptopurine + ?
show the reaction diagram
-
-
-
?
glutathione + benzo[a]pyrene 4,5-oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + bromosulfophthalein
?
show the reaction diagram
-
-
-
-
?
glutathione + chlorambucil
?
show the reaction diagram
-
-
-
-
?
glutathione + cis-6-(2-acetylvinylthio)purine
?
show the reaction diagram
-
-
-
?
glutathione + cryptophycin 52
?
show the reaction diagram
-
conjugation with the R-stereoisomer
-
-
?
glutathione + cryptophycin 53
?
show the reaction diagram
-
conjugation with the S-stereoisomer
-
-
?
glutathione + cumene hydroperoxide
?
show the reaction diagram
-
-
-
-
?
glutathione + ethacrynic acid
?
show the reaction diagram
glutathione + ethylene diiodide
?
show the reaction diagram
-
-
-
?
glutathione + iodomethane
?
show the reaction diagram
-
-
-
-
?
glutathione + styrene 7,8-oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + styrene oxide
?
show the reaction diagram
-
-
-
-
?
glutathione + trans-4-phenyl-3-buten-2-one
?
show the reaction diagram
-
-
-
-
?
glutathione + trans-6-(2-acetylvinylthio)guanine
?
show the reaction diagram
-
-
-
?
hydrogen peroxide + glutathione
?
show the reaction diagram
-
-
-
-
?
maleylacetone + glutathione
?
show the reaction diagram
-
-
-
-
?
monochlorobimane + glutathione
bimane-glutathione + HCl
show the reaction diagram
-
-
-
-
?
nonenal + glutathione
?
show the reaction diagram
-
-
-
-
?
phenethyl isothiocyanate + glutathione
?
show the reaction diagram
-
-
-
-
?
propyl isothiocyanate + glutathione
?
show the reaction diagram
-
-
-
-
?
rac-4-hydroxynonenal + glutathione
S-(4-hydroxy-1-oxononan-3-yl)glutathione
show the reaction diagram
-
elimination of the lipid peroxidation product 4-hydroxynonenal, a toxic compound that contributes to numerous diseases
-
-
?
rac-4-hydroxynonenal + glutathione
S-[(2S)-3-hydoxy-2-(2-oxoethyl)octyl]glutathione
show the reaction diagram
-
GSTA1-1 isoform has poor catalytic efficiency with 4-hydroxynonenal, GSTA4-4 has negligible stereoselectivity towards the two 4-hydroxynonenal enantiomers, despite its high catalytic chemospecificity for alkenals
product binding, overview
-
?
RSSR + glutathione
glutathione-SSR + R-SH
show the reaction diagram
-
-
-
?
RX + glutathione
HX + R-S-G
show the reaction diagram
styrene oxide + glutathione
?
show the reaction diagram
-
-
-
-
?
tertiary butyl hydroperoxide + glutathione
?
show the reaction diagram
-
-
-
-
?
[(methylamino)[methyl(nitroso)amino]methyl]cyanamide + glutathione
[bis(methylamino)methyl]cyanamide + S-nitrosoglutathione
show the reaction diagram
-
transnitrosylation
-
-
?
[3-(4-nitrophenyl)oxiran-2-yl]methanol + glutathione
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
brostallicin + glutathione
glutathionyl-brostallicin
show the reaction diagram
-
involved in activation of the prodrug, mechanism, overview. The reaction proceeds via the alpha-chloroamido derivative of the GSH-brostallicin adduct, is able to alkylate DNA in a sequence-specific manner and appears to be the active form of the drug, brostallicin cytotoxicity of brostallicin is higher in cells overexpressing either the GST-pi or the GST-mu gene
-
-
?
rac-4-hydroxynonenal + glutathione
S-(4-hydroxy-1-oxononan-3-yl)glutathione
show the reaction diagram
-
elimination of the lipid peroxidation product 4-hydroxynonenal, a toxic compound that contributes to numerous diseases
-
-
?
RX + glutathione
HX + R-S-G
show the reaction diagram
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-catechin hydrate
-
inhibition of isozymes GST M1-1 and M2-2
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
a coumaroflavan from Treculia africana, 26% total inhibition at 0.033 mM
(2Z)-2-[(4-methoxyphenyl)carbonyl]-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid
-
-
(2Z)-2-[(4-methylphenyl)carbonyl]-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid
-
-
(2Z)-2-[(4-methylphenyl)carbonyl]-3-phenylprop-2-enoic acid
-
8.1% inhibition at 0.02 mM
(2Z)-3-(1,3-benzodioxol-5-yl)-2-[(4-methoxyphenyl)carbonyl]prop-2-enoic acid
-
10% inhibition at 0.02 mM
(2Z)-3-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
9.6% inhibition at 0.02 mM
(2Z)-3-(2-methylphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
9.3% inhibition at 0.02 mM
(2Z)-3-(3,4-dihydroxyphenyl)-2-[(4-methoxyphenyl)carbonyl]prop-2-enoic acid
-
-
(2Z)-3-(3,4-dihydroxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
-
(2Z)-3-(3-hydroxyphenyl)-2-[(4-methoxyphenyl)carbonyl]prop-2-enoic acid
-
6.6% inhibition at 0.02 mM
(2Z)-3-(3-hydroxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
13.9% inhibition at 0.02 mM
(2Z)-3-(3-methoxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
19.0% inhibition at 0.02 mM
(2Z)-3-(4-chlorophenyl)-2-[(4-methoxyphenyl)carbonyl]prop-2-enoic acid
-
14.4% inhibition at 0.02 mM
(2Z)-3-(4-chlorophenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
14.4% inhibition at 0.02 mM
(2Z)-3-(4-fluorophenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
-
(2Z)-3-(4-hydroxy-3-methoxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
8.8% inhibition at 0.02 mM
(2Z)-3-(4-hydroxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
12.5% inhibition at 0.02 mM
(2Z)-3-(4-methoxyphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
-
(2Z)-3-(4-methylphenyl)-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
-
(2Z)-3-[4-(dimethylamino)phenyl]-2-[(4-methylphenyl)carbonyl]prop-2-enoic acid
-
9.3% inhibition at 0.02 mM
(4S,6Z,10Z,11aS)-4-ethoxy-6-(hydroxymethyl)-3-methylidene-10-propoxy-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
-
a sesquiterpene lactone from Dicoma anomala collected from Namibia, 75% total inhibition at 0.033 mM
1,4-pentadiene-3-one
-
curcumin derivative
1,7-dihydroxyanthracen-9(10H)-one
-
a xanthone from Mammea africana, 21% total inhibition at 0.033 mM
1-chloro-2,4-dinitrobenzene
-
competitive inhibition by the substrate
1-methyl-2-[((2-nitrobenzyl)sulfonyl)]-1H-pyrrole
-
44.3% inhibition at 0.1 mM
1-methyl-2-[(2-nitrobenzyl)sulfanyl]-1H-pyrrole
-
-
2,5-dibenzylidenecyclopentanone
-
curcumin derivative
2,6-dibenzylidenecyclohexanone
-
curcumin derivative
2-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)imidazole
-
-
2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)-N-((1E)-[4-(trifluoromethyl)phenyl]methylene)aniline
-
68.4% inhibition at 0.1 mM
2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)-N-[(1E)-(4-nitrophenyl)methylene]aniline
-
90.0% inhibition at 0.1 mM
2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)-N-[(1E)-(phenyl)methylene]aniline
-
30.2% inhibition at 0.1 mM
2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)-N-[(1E)-1H-pyrrol-2-ylmethylene]aniline
-
36.0% inhibition at 0.1 mM
2-hydroxyanthracen-9(10H)-one
-
a xanthone Mammea from africana, 38% total inhibition at 0.033 mM
2-[(1-methyl-1H-pyrrol-2-ylsulfonyl)methyl]aniline
-
28.0% inhibition at 0.1 mM
3-(3,4-dihydroxybenzoyl)-4-hydroxy-8-methyl-1,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
-
a benzophenone Garcinia smeathmannii, 41% total inhibition at 0.033 mM
3-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)propionic acid
-
-
3-ethyl-2-oxo-3,3a,7a,9b-tetrahydro-2H,4aH-1,4,5-trioxadicyclopenta[a,hi]indene-7-carboxylic acid
-
an iridoid from Plumeeria rubra, 51% total inhibition at 0.033 mM
4-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)butanol
-
-
4-(acryloylamino)-N-(5-[[5-([5-[(2-carbamimidamidoethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl)-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
-
a brostallicin derivative, the debrominated derivative of brostallicin is almost completely ineffective as an inhibitor of GSTP1-1
4-[(2-bromoacryloyl)amino]-N-(5-[[5-([5-[(2-carbamimidamidoethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl)-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
-
i.e. brostallicin, mixed-type inhibition, inhibits GSTP1-1 and GSTM2-2, thereby being much more efficient in inhibiting GSTM2-2 than in inhibiting GSTP1-1. Brostallicin sensitivity for brostallicin is higher in cells overexpressing either the GST-pi or the GST-mu gene
4-[3-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)-3-hydroxybutoxy]-7H-furo[3,2-g]chromen-7-one
-
a furocoumarin from Dorstenia elliptica, 34% total inhibition at 0.033 mM
5,7-dihydroxy-6-(2-hydroxybutanoyl)-8-(3-methylbut-2-en-1-yl)-4-propyl-2H-chromen-2-one
-
a coumarin from Mammea africana, 33% total inhibition at 0.033 mM
5,8-dihydroxy-1-(hydroxymethyl)naphtho[2,3-c]furan-4,9-dione
-
an isofuranonapthoquinone from Bulbine frutescens, the mode of inhibition is mixed, partial (G site) and noncompetitive (H site), 68% total inhibition at 0.033 mM
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-(4-chlorobenzyl)-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-(4-fluorophenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-(4-methoxyphenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-(4-nitrobenzyl)-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-methyl-1,2,4-oxadiazol
-
-
5-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxymethyl]-3-phenyl-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-chlorobenzyl)-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-fluorophenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-hydroxyphenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-nitrobenzyl)-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-methyl-1,2,4-oxadiazol
-
-
5-[2,3-dimethyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-phenyl-1,2,4-oxadiazol
-
-
5-[3-bromo-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-fluorophenyl)-1,2,4-oxadiazol
-
-
5-[3-bromo-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol
-
-
5-[3-bromo-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-methyl-1,2,4-oxadiazol
-
-
5-[3-bromo-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-phenyl-1,2,4-oxadiazol
-
-
5-[3-chloro-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-fluorophenyl)-1,2,4-oxadiazol
-
-
5-[3-chloro-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol
-
-
5-[3-chloro-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-methyl-1,2,4-oxadiazol
-
-
5-[3-chloro-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-phenyl-1,2,4-oxadiazol
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-fluorophenyl)-1,2,4-oxadiazol
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-hydroxyphenyl)-1,2,4-oxadiazol
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-nitrobenzyl)-1,2,4-oxadiazol
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-methyl-1,2,4-oxadiazole
-
-
5-[3-methyl-4-(2-methylene-1-oxopropyl)phenoxymethyl]-3-phenyl-1,2,4-oxadiazole
-
-
6-(7-nitro-2,1,3-benzoxadiazol-4-ylamino)hexanol
-
-
6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol
-
-
6-butanoyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one
-
a coumarin from Mammea africana, 23% total inhibition at 0.033 mM
7-nitro-2,1,3-benzoxadiazole derivatives
-
non-GSH peptidomimetic compounds, suicide inhibitors of the enzyme, binding structure and mechanism, overview, the compounds show strong GST inhibition and accumulation in tumor cells avoiding the extrusion mechanisms mediated by the multidrug resistance protein pumps
-
bilirubin
bromosulfophthalein
chlorambucil
-
very poor inhibitor of the enzyme in contrast to ethacrynic acid
curcumin
daidzein
-
inhibition of isozymes GST A1-1, M1-1, and P1-1
Dichloroacetic acid
i.e. DC, used to treat lactic acidosis and has also been proposed as a novel anticancer agent is both a substrate and a mechanism-based inactivator of GSTZ1-1. Treatment with DCA progressively inactivates GSTZ1-1 and increases the elimination half-life of subsequent doses of DCA. recombinant GSTZ1*A protein is relatively resistant to DCA mediated inactivation when compared with the other isoforms
dieldrin
-
a potent reversible inhibitor toward hGSTA1-1, mixed-type inhibition, dieldrin binds specifically to the enzyme presumably at a position that partially overlaps with both the G- and H-site, a site distinct from binding of spiromesifen, binding structure overview
ellagic acid
-
inhibition of isozymes GST A1-1, A2-2, M1-1, M2-2, and P1-1, effects on substrate kinetics, overview
Ethacrynic acid
ferulic acid
-
inhibition of isozyme GST M1-1
genistein
-
inhibition of isozymes GST M1-1 and M2-2
glutathione
-
competitive inhibition by the substrate
Hematin
kaempferol
-
inhibition of isozymes GST M1-1 and M2-2
L-g-glutamyl-S-[3-([5-[(5-[[5-([5-[(2-carbamimidamidoethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl)-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]amino)-2-hydroxy-3-oxopropyl]-L-cysteinylglycine
-
a brostallicin derivative, inhibits GSTP1-1 and GSTM2-2
L-g-glutamyl-S-[3-([5-[(5-[[5-([5-[(2-carbamimidamidoethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl)-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]amino)-3-oxo-2-(phosphonooxy)propyl]-L-cysteinylglycine
-
a brostallicin derivative, inhibits GSTP1-1 and GSTM2-2
N-((1E)-[4-(dimethylamino)phenyl]methylene)-2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)aniline
-
78.9% inhibition at 0.1 mM
N-acetyl-p-benzoquinoneimine
-
concentration-dependent inhibition
N-ethylmaleimide
N-[(1E)-(2-chlorophenyl)methylene]-2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)aniline
-
88.8% inhibition at 0.1 mM
N-[(1E)-(4-chlorophenyl)methylene]-2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)aniline
-
60.4% inhibition at 0.1 mM
N-[(1E)-(4-fluorophenyl)methylene]-2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)aniline
-
37.1% inhibition at 0.1 mM
N-[(1E)-(5-bromo-2-methoxyphenyl)methylene]-2-([(1-methyl-1H-pyrrol-2-yl)sulfonyl]methyl)aniline
-
646% inhibition at 0.1 mM
Prostaglandins
-
isozyme GST P1-1 forms covalent complexes with cyclopentenone prostaglandins, i.e. cyPG 15-deoxy-DELTA12,14-PGJ2 and biotinylated 15d-PGJ2, mass spectrometry analysis, overview, irreversible inhibition
-
quercetin
-
inhibition of isozymes GST M1-1 and M2-2
resveratrol
-
inhibition of isozymes GST A2-2, M1-1, M2-2, and P1-1
S-(2,4-dinitrophenyl)glutathione
-
product inhibition
S-(2,4-dinitrophenyl)GSH
-
-
S-(4-azidophenacryl)-glutathione
-
competitive inhibitor, 27% loss of activity after 5 min
S-hexyl glutathione
-
S-hexylglutathione
S-methyl-GSH
-
-
S-Methylglutathione
-
competitive
spiromesifen
-
a potent reversible inhibitor toward hGSTA1-1, mixed-type inhibition, spiromesifen binds specifically to the enzyme presumably at a position that partially overlaps with both the G- and H-site, a site distinct from binding of dieldrin, binding structure overview
Tributyltin acetate
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.023 - 0.417
(+)-2-bromo-3-(4-nitrophenyl)propanoic acid
4.2 - 8.8
(R)-styrene-7,8-oxide
0.8 - 2.4
(R,R)-1-phenylpropylene oxide
0.035 - 0.1
(R,R)-trans-stilbene oxide
1.3 - 4.9
(S)-styrene-7,8-oxide
2.2 - 3.8
(S,S)-1-phenylpropylene oxide
0.08 - 0.12
(S,S)-trans-stilbene oxide
0.27 - 0.84
1,2-dichloro-4-nitrobenzene
0.13 - 1.84
1,2-epoxy-3-(p-nitrophenoxy)propane
0.6 - 1
1,3-Bis-(2-chloroethyl)-1-nitrosourea
0.17 - 6.6
1-chloro-2,4-dinitrobenzene
0.232
3,4-dinitrobenzanilide
-
in phosphate buffered saline, pH 7.4, at 37°C
0.002 - 0.011
7-chloro-4-nitrobenz-2-oxa-1,3-diazole
0.005
brostallicin
-
pH 6.5, 25°C, GSTM2-2
0.00324
cryptophycin 52
-
pH 7.4, 37°C
0.3 - 8
cumene hydroperoxide
0.06 - 0.21
Ethacrynic acid
0.003 - 123.6
glutathione
0.0139 - 1.76
GSH
0.083
iodobutane
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.058
iodohexane
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.085
iodomethane
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.064 - 0.768
maleylacetone
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.19 - 13
(+)-2-bromo-3-(4-nitrophenyl)propanoic acid
2.7 - 4.8
(R)-styrene-7,8-oxide
0.83 - 17.7
(R,R)-1-phenylpropylene oxide
0.37 - 7.7
(R,R)-trans-stilbene oxide
2.3 - 8.4
(S)-styrene-7,8-oxide
1.1 - 9
(S,S)-1-phenylpropylene oxide
0.07 - 0.46
(S,S)-trans-stilbene oxide
110 - 320
1,2-dichloro-4-nitrobenzene
31 - 302
1,2-epoxy-3-(p-nitrophenoxy)propane
0.035 - 3.6
1,3-Bis-(2-chloroethyl)-1-nitrosourea
1.19 - 761
1-chloro-2,4-dinitrobenzene
106
1-Fluoro-2,4-dinitrobenzene
-
-
367
3,4-dinitrobenzanilide
-
in phosphate buffered saline, pH 7.4, at 37°C
200 - 9600
cumene hydroperoxide
0.17 - 47.3
glutathione
0.19 - 1700
GSH
0.037
iodobutane
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.068
iodohexane
-
pH 8.0, 30°C, recombinant wild-type enzyme
9.16
iodomethane
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.347 - 464
maleylacetone