2.1.1.100: protein-S-isoprenylcysteine O-methyltransferase
This is an abbreviated version!
For detailed information about protein-S-isoprenylcysteine O-methyltransferase, go to the full flat file.
Word Map on EC 2.1.1.100
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2.1.1.100
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n-acetyl-s-farnesyl-l-cysteine
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cysmethynil
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medicine
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a-factor
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aax
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carboxylmethylation
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ste24p
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n-acetyl-s-geranylgeranyl-l-cysteine
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ras-driven
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biotechnology
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analysis
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drug development
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pharmacology
- 2.1.1.100
- n-acetyl-s-farnesyl-l-cysteine
- cysmethynil
- medicine
- a-factor
- aax
-
carboxylmethylation
- ste24p
- n-acetyl-s-geranylgeranyl-l-cysteine
-
ras-driven
- biotechnology
- analysis
- drug development
- pharmacology
Reaction
Synonyms
EC 2.1.1.24, farnesyl cysteine C-terminal methyltransferase, farnesyl-protein carboxymethyltransferase, farnesylated protein C-terminal O-methyltransferase, Icmt, isoprenylated protein methyltransferase, isoprenylcysteine carboxyl methyltransferase, isoprenylcysteine carboxylmethyltransferase, isoprenylcysteine carboxylmethyltransferase Ste14p, isoprenylcysteine methylesterase, methyltransferase, protein C-terminal farnesylcysteine O-, prenylated protein methyltransferase, protein S-farnesylcysteine C-terminal methyltransferase, S-farnesylcysteine methyltransferase, STE14A, STE14B, Ste14p
ECTree
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Inhibitors
Inhibitors on EC 2.1.1.100 - protein-S-isoprenylcysteine O-methyltransferase
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(2R)-2-(acetylamino)-3-[[(2Z)-3,4-diphenylbut-2-en-1-yl]sulfanyl]propanoic acid
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15.7% inhibition at 0.01 mM
(2R)-2-(acetylamino)-3-[[(2Z)-4-(2-fluorophenyl)-3-phenylbut-2-en-1-yl]sulfanyl]propanoic acid
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25.3% inhibition at 0.01 mM
(3,5-difluoro-4-methoxyphenyl)-[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]amine
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(3-chloro-4-fluorophenyl)-[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]amine
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(3-chlorophenyl)-[2-(2,2-dimethyl-4-thiophen-2-yltetrahydropyran-4-yl)ethyl]amine
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(4-chloro-3-fluorophenyl)-[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]amine
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(5-chloro-2-fluorophenyl)-[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]amine
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(R)-2-(2-((benzyloxy)methyl)benzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)-thio)propanoic acid
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(R)-2-(2-(phenoxymethyl)benzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R)-2-(2-(phenylthio)benzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R)-2-(2-benzylbenzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R)-2-(2-phenoxybenzamido)-3-(((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)thio)propanoic acid
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(R)-2-(3-phenoxybenzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R)-2-(4-phenoxybenzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R)-2-(dibenzo[b,d]furan-4-carboxamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)-propanoic acid
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(R)-2-(N-methyl-2-phenoxybenzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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(R,E)-3-((3,7-dimethylocta-2,6-dien-1-yl)thio)-2-(2-phenoxybenzamido)propanoic acid
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(S)-2-(2-phenoxybenzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid
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1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-3-(morpholin-4-ylmethyl)-1H-indole
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1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-3-(piperidin-1-ylmethyl)-1H-indole
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1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-3-[(morpholin-4-yl)methyl]-1H-indole
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1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-3-[(piperidin-1-yl)methyl]-1H-indole
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2'-methoxy-3',3''-diprenyl-licodione
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isolated from Hovea parvicalyx, collected in Australia, structure determination, overview
2'-methoxy-3'-prenyllicodione
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isolated from Hovea parvicalyx, collected in Australia, structure determination, overview
2-[1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-1H-indol-3-yl]acetamide
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2-[1-[(2E,6E)-2,6-dimethylocta-2,6-dien-1-yl]-5-(3-methylphenyl)-1H-indol-3-yl]acetamide
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2-[5-(3-fluorophenyl)-1-(2-methylidenebut-3-en-1-yl)-1H-indol-3-yl]acetamide
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2-[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]-1-(4-methylpiperazin-1-yl)ethan-1-one
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2-[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]-1-(4-methylpiperazin-1-yl)ethanone
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2-[5-(3-methylphenyl)-1-[[3-(trifluoromethyl)phenyl]methyl]-1H-indol-3-yl]acetamide
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2-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl](phenyl)amino]-1-(furan-2-yl)ethanone
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3,4-dichloro-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2Hpyran-4-yl)ethyl]aniline
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3,5-dichloro-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]aniline
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3-(2,2-dimethyloxan-4-yl)-N-[(4-methoxyphenyl)methyl]-3-phenylpropan-1-amine
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3-([(2E)-3-methyl-5-[4-(2-phenylethyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoic acid
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75% residual activity at 0.01 mM
3-([(2E)-3-methyl-5-[4-(3-methylbutyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoic acid
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modest inhibitor, 72% residual activity at 0.01 mM
3-([(2E)-3-methyl-5-[4-(naphthalen-1-yl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoic acid
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poor inhibitor, 77% residual activity at 0.01 mM
3-([(2E)-3-methyl-5-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoic acid
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89% residual activity at 0.01 mM
3-([(2E)-3-methyl-5-[4-(thiophen-3-yl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoic acid
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poor inhibitor, 80% residual activity at 0.01 mM
3-([(2E)-5-[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl)propanoic acid
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poor inhibitor, 87% residual activity at 0.01 mM
3-([(2E)-5-[4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl)propanoic acid
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poor inhibitor, 88% residual activity at 0.01 mM
3-chloro-4-methyl-N-[2-(2,2,6,6-tetramethyl-4-phenyl-4-piperidyl)ethyl]aniline
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3-chloro-N-(3-chlorophenyl)-N-[2-(2,2,6,6-tetramethyl-4-phenyltetrahydropyran-4-yl)ethyl]aniline
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3-chloro-N-[2-(2,2,6,6-tetramethyl-4-phenyltetrahydrothiopyran-4-yl)ethyl]aniline
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3-chloro-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]-4-methylaniline
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3-methoxy-N-[2-(2,2,6,6-tetramethyl-4-phenyltetrahydropyran-4-yl)ethyl]aniline
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3-methoxy-N-[2-(2,2,6,6-tetramethyl-4-phenyltetrahydrothiopyran-4-yl)ethyl]aniline
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3-methoxy-N-[2-[4-(4-methoxyphenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl]ethyl]aniline
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3-tert-butyl-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]aniline
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3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]propanoic acid
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modest inhibitor, 53% residual activity at 0.01 mM
3-[4-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-1H-1,2,3-triazol-1-yl]propanoic acid
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modest inhibitor, 75% residual activity at 0.01 mM
3-[4-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-1H-1,2,3-triazol-1-yl]propanoic acid
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modest inhibitor, 69% residual activity at 0.01 mM
3-[[(2E)-3-methyl-5-(4-pentyl-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoic acid
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modest inhibitor, 77% residual activity at 0.01 mM
3-[[(2E)-3-methyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoic acid
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poor inhibitor, 88% residual activity at 0.01 mM
3-[[(2E)-3-methyl-5-(4-[2-[4-(thiophen-2-yl)phenyl]ethyl]-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoic acid
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63% residual activity at 0.01 mM
3-[[(2E)-3-methyl-5-[4-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl]propanoic acid
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90% residual activity at 0.01 mM
3-[[(2E)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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82% residual activity at 0.01 mM
3-[[(2E)-5-[4-[(biphenyl-4-yloxy)methyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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75% residual activity at 0.01 mM
3-[[(2E)-5-[4-[2-(3'-cyanobiphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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74% residual activity at 0.01 mM
3-[[(2E)-5-[4-[2-(4'-fluorobiphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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42% residual activity at 0.01 mM
3-[[(2E)-5-[4-[2-(biphenyl-3-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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74% residual activity at 0.01 mM
3-[[(2E)-5-[4-[2-(biphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoic acid
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43% residual activity at 0.01 mM
3-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]amino]-N,N-dimethylbenzenesulfonamide
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3-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]amino]benzonitrile
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4-chloro-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]-3-methylaniline
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4-tert-butyl-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]aniline
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4-[(naphthalen-2-yl)(thiophen-2-yl)methylidene]oxane
competitive with the prenylated peptide substrate, N-acetyl-S-farnesyl cysteine and non-competitive with SAM
4-[3-[(diethylamino)methyl]-1-octyl-1H-indol-5-yl]-N-methylbenzene-1-sulfonamide
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4-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]butanoic acid
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modest inhibitor, 83% residual activity at 0.01 mM
4-[4-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-1H-1,2,3-triazol-1-yl]butanoic acid
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modest inhibitor, 90% residual activity at 0.01 mM
4-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]amino]benzenesulfonamide
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4-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]amino]benzonitrile
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5-(3-methylphenyl)-3-[(4-methylpiperazin-1-yl)methyl]-1-octyl-1H-indole
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5-[3-[(diethylamino)methyl]-1-octyl-1H-indol-5-yl]-N,N-dimethylpyridin-2-amine
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5-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]pentanoic acid
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modest inhibitor, 73% residual activity at 0.01 mM
ethyl 4-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]amino]benzoate
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methyl 3-([(2E)-3-methyl-5-[4-(2-phenylethyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoate
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69% residual activity at 0.01 mM
methyl 3-([(2E)-3-methyl-5-[4-(3-methylbutyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoate
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modest inhibitor, 77% residual activity at 0.01 mM
methyl 3-([(2E)-3-methyl-5-[4-(naphthalen-1-yl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoate
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poor inhibitor, 82% residual activity at 0.01 mM
methyl 3-([(2E)-3-methyl-5-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoate
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89% residual activity at 0.01 mM
methyl 3-([(2E)-3-methyl-5-[4-(thiophen-3-yl)-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl)propanoate
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poor inhibitor, 82% residual activity at 0.01 mM
methyl 3-([(2E)-5-[4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl)propanoate
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poor inhibitor, 91% residual activity at 0.01 mM
methyl 3-([(2E)-5-[4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl)propanoate
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poor inhibitor, 84% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-(4-nonyl-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoate
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modest inhibitor, 67% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-(4-pentyl-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoate
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modest inhibitor, 76% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-(4-phenyl-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoate
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poor inhibitor, 89% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-(4-[2-[4-(thiophen-2-yl)phenyl]ethyl]-1H-1,2,3-triazol-1-yl)pent-2-en-1-yl]sulfanyl]propanoate
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57% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-[4-[2-(1,1':4',1''-terphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl]propanoate
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79% residual activity at 0.01 mM
methyl 3-[[(2E)-3-methyl-5-[4-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-1,2,3-triazol-1-yl]pent-2-en-1-yl]sulfanyl]propanoate
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80% residual activity at 0.01 mM
methyl 3-[[(2E)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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80% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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modest inhibitor, 59% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[(biphenyl-4-yloxy)methyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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67% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-(3'-cyanobiphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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30% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-(4'-fluorobiphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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28% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-(biphenyl-2-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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74% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-(biphenyl-3-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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65% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-(biphenyl-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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potent competitive inhibitor, 14% residual activity at 0.01 mM
methyl 3-[[(2E)-5-[4-[2-([1,1'-biphenyl]-4-yl)ethyl]-1H-1,2,3-triazol-1-yl]-3-methylpent-2-en-1-yl]sulfanyl]propanoate
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N'-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-N,N-dimethylbenzene-1,3-diamine
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N,N-dimethyl-1-[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]methanamine
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N-(2-methylidenebut-3-en-1-yl)-2-[5-(3-methylphenyl)-1-[3-(trifluoromethyl)benzyl]-1H-indol-3-yl]acetamide
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N-(2-phenoxybenzoyl)-3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]-L-alanine
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35.9% inhibition at 0.01 mM
N-(2-phenoxybenzoyl)-S-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-L-cysteine
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N-(3-[[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]amino]phenyl)acetamide
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N-(5-methoxy-2-nitrobenzoyl)-3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]-L-alanine
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10.1% inhibition at 0.01 mM
N-(biphenyl-2-ylcarbonyl)-3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]-L-alanine
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17% inhibition at 0.01 mM
N-acetyl-3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]-L-alanine
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19.5% inhibition at 0.01 mM
N-acetyl-S-(3-(3-methylbut-2-enyl)-7,11-dimethyldodeca-2Z,6E,10-trien-1-yl)-L-cysteine
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competitive inhibitor of overexpressed yeast Icmt
N-acetyl-S-(E,E)-farnesyl-L-cysteine methyl ester
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mixed-type vs. N-acetyl-S-(E,E)-farnesyl-L-cysteine
N-acetyl-S-farnesyl-L-cysteine methylester
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noncompetitive inhibition with respect to biotin-S-farnesyl-L-cysteine, mixed type inhibition with respect to S-adenosyl-L-methionine
N-acetyl-S-[(2E)-3-methyl-4-(4-phenoxyphenoxy)but-2-en-1-yl]-L-cysteine
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15.5% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-4-[(naphthalen-2-ylamino)oxy]but-2-en-1-yl]-L-cysteine
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14.5% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-5-(4-octylphenyl)pent-2-en-1-yl]-L-cysteine
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31.1% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-5-(4-pentylphenyl)pent-2-en-1-yl]-L-cysteine
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23.1% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-5-(4-propylphenyl)pent-2-en-1-yl]-L-cysteine
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20.7% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-7-(4-phenoxyphenoxy)hept-2-en-1-yl]-L-cysteine
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19.4% inhibition at 0.01 mM
N-acetyl-S-[(2E)-3-methyl-7-[(naphthalen-2-ylamino)oxy]hept-2-en-1-yl]-L-cysteine
-
22.4% inhibition at 0.01 mM
N-acetyl-S-[(2E)-4-(4-benzylphenoxy)-3-methylbut-2-en-1-yl]-L-cysteine
-
9.8% inhibition at 0.01 mM
N-acetyl-S-[(2E)-5-(4-hexylphenyl)-3-methylpent-2-en-1-yl]-L-cysteine
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18.8% inhibition at 0.01 mM
N-acetyl-S-[(2Z)-4-(biphenyl-4-yl)-3-phenylbut-2-en-1-yl]-L-cysteine
-
26.6% inhibition at 0.01 mM
N-benzyl-N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]furan-2-carboxamide
-
-
N-bromosuccinimide
-
56% inhibition in the presence of S-adenosyl-L-homocysteine, 87% inhibition in the absence of S-adenosyl-L-homocysteine
N-ethyl-N-([1-octyl-5-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl]methyl)ethanamine
-
-
N-ethyl-N-([5-[4-(methanesulfonyl)phenyl]-1-octyl-1H-indol-3-yl]methyl)ethanamine
-
-
N-ethyl-N-[[1-(2-methylidenebut-3-en-1-yl)-5-(3-methylphenyl)-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(2-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(3-fluorophenyl)-1-(2-methylidenebut-3-en-1-yl)-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(3-fluorophenyl)-1-octyl-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(3-fluoropyridin-4-yl)-1-octyl-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]ethanamine
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N-ethyl-N-[[5-(4-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]ethanamine
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N-methyl-N-[[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]propan-2-amine
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N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2-[5-(3-methylphenyl)-1-[3-(trifluoromethyl)benzyl]-1H-indol-3-yl]acetamide
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3,4-dimethoxyaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3,5-dimethylaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3-(trifluoromethoxy)aniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3-(trifluoromethyl)aniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3-isopropylaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3-methoxy-4-methylaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-3-methoxyaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-4-(trifluoromethoxy)aniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-4-isopropylaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-4-methoxyaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-N,3-dimethylaniline
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)-ethyl]-N-phenylacetamide
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N-[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]-3,4-dimethylaniline
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N-[2-(benzyloxy)benzoyl]-S-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-L-cysteine
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N-[3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-3-(2-methoxyphenyl)propyl]-N-(4-methoxybenzyl)furan-2-carboxamide
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the inhibitor is competitive with respect to a prenylated methyl acceptor substrate but noncompetitive toward the S-adenosyl-L-methionine
N-[3-(phenylsulfonyl)propanoyl]-3-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]-L-alanine
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22.7% inhibition at 0.01 mM
N-[[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]-N-(propan-2-yl)propan-2-amine
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N-[[5-(3-methylphenyl)-1-octyl-1H-indol-3-yl]methyl]-N-propylpropan-1-amine
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Phenylglyoxal
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74% inhibition, inhibition increases with the alkanity of the preincubation medium, S-adenosyl-L-methionine protects against inhibition
retinoic acid
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20% decrease of N-acetyl-S-(E,E)-farnesyl-L-cysteine methylation in cells treated with 0.01 mM retinoic acid
S-[(2E)-3-[2-([1,1'-biphenyl]-4-yl)ethyl]-6-methylhepta-2,5-dien-1-yl]-N-(2-phenoxybenzoyl)-L-cysteine
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S-[(2E,6E)-8-(3-benzoylphenoxy)-3,7-dimethylocta-2,6-dien-1-yl]-N-([2-[2-([5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)ethoxy]ethoxy]acetyl)-D-cysteine
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S-{(2E)-3-[2-(biphenyl-4-yl)ethyl]-6-methylhepta-2,5-dien-1-yl}-N-(2-phenoxybenzoyl)-L-homocysteine
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low micromolar inhibitor
[2-(2,2-dimethyl-4-p-tolyltetrahydropyran-4-yl)ethyl]-(3-methoxyphenyl)amine
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[2-(2,2-dimethyl-4-phenyltetrahydro-2H-pyran-4-yl)ethyl]-(2-fluorophenyl)amine
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[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]-(2-fluoro-4-methylphenyl)amine
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[2-(2,2-dimethyl-4-phenyltetrahydropyran-4-yl)ethyl]-(3-fluoro-4-methoxyphenyl)amine
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[2-(2,2-dimethyl-4-thiophen-2-yltetrahydropyran-4-yl)-ethyl]-(3-methoxyphenyl)amine
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[2-[4-(3-chlorophenyl)-2,2-dimethyltetrahydropyran-4-yl]-ethyl]-(3-methoxyphenyl)amine
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[2-[4-(3-fluoro-phenyl)-2,2-dimethyltetrahydropyran-4-yl]-ethyl]-(3-methoxyphenyl)amine
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[2-[4-(4-chlorophenyl)-2,2-dimethyltetrahydropyran-4-yl]-ethyl]-(3-methoxyphenyl)amine
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[2-[4-(4-fluorophenyl)-2,2-dimethyltetrahydropyran-4-yl]-ethyl]-(3-methoxyphenyl)amine
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[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-1H-1,2,3-triazol-1-yl]acetic acid
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modest inhibitor, 65% residual activity at 0.01 mM
aplysamine 6
Pseudoceratina sp.
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i.e. (2E)-N-{2-[4-(3-aminopropoxy)-3,5-dibromophenyl]ethyl}-3-(3-bromo-4-methoxyphenyl)acrylamide
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most potent time-dependent inhibitor, inhibition of cell growth in an Icmt-dependent fashion
cysmethynil
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specific inhibitor, is also able to inhibit Ras-mediated signaling, cell growth, and oncogenesis, and it affects cell adhesion and cell spreading
cysmethynil
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time-dependent inhibitor, competitive inhibitor with respect to the isoprenylated cysteine substrate and a noncompetitive inhibitor with respect to S-adenosyl-L-methionine
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shows a mix of competitive and uncompetitive inhibition
N-Acetyl-S-(3-(3-methylbut-2-enyl)-5-(4-phenyl)phenylpent-2Z-en-1-yl)-L-cysteine
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shows a mix of competitive and uncompetitive inhibition
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inhibition of N-acetyl-S-farnesyl-L-cysteine methylation
N-ethylmaleimide
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2 mM, 94% inhibition after preincubation for 30 min, 45% inhibition in the presence of S-adenosyl-L-homocysteine
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competitive vs. S-adenosyl-L-methionine, mixed-type vs. N-acetyl-S-(E,E)-farnesyl-L-cysteine
S-adenosyl-L-homocysteine
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0.2 mM, 67% inhibition of the endogenous methylation of 21000-25000 Da proteins
S-adenosyl-L-homocysteine
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competitive inhibitor with respect to S-adenosyl-L-methionine
sinefungin
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0.00002 mM; 50% inhibition, competitive vs. S-adenosyl-L-methionine
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FC analogs containing larger R-groups inhibit Icmt more effectively than those with smaller R-groups, in particular, an adamantyl analog is the most potent inhibitor. Also compounds containing 3,5-disubstituted phenyl rings, with the exception of a difluoro compound, exhibit inhibitory activity, whereas the corresponding 2,4-disubstituted analogs do not
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additional information
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good inhibitory activity is determined largely by the characteristics of the substituent attached to the indole nitrogen, which should be a lipophilic residue with fairly wide dimensions. In contrast, the substituted phenyl ring attached to the indole ring must be of limited dimensions and lipophilicity
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additional information
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decrease in the length versus hydrophobicity of the indole nitrogen substituent is accompanied by loss of the time-dependent properties of this indole class of Icmt inhibitors
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