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(24,S),25-epiminozymosterol
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(24R)-methyl-25-thiacholesteryl iodide
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(24R,S),25-epiminolanosterol
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(24R,S),25-epiminozymosterol
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(24S)-methyl-25-thiacholesteryl iodide
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(3beta,24,R,S)-24-methyl-24-thioniacholest-5-enol
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(3S,20R)-20-(propylamino-ethyl)-pregn-7-en-3-ol
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(3S,20S)-20-(butylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(ethylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(methylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(pentylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(propylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-[(1R,S)-(1,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-dimethylamino-ethylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-methylpropyl)amino-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-pyrrolidin-1-yl-ethylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(3-dimethylamino-propylamino)-methyl]-pregn-7-en-3-ol
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(R,S)-24,25-epiminolanosterol
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(R,S)-S-butyl-S-[(3S,20S)-(3-hydroxypregn-7-en-20-yl)-methyl]-S-methyl-sulfonium iodide
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2-(3S,20R)-[(E)-2-(3-hydroxypregn-7-en-20-yl)-ethenyl]-1-methylpyridinium iodide
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22,25-Diazacholesterol
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20R and 20S isomer
22-piperidin-3-yl-pregnan-22(S),3beta-diol
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24(R,S),25-epiminolanosterol
24(R,S),25-epiminozymosterol
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reversible inhibitor, disrupts ergosterol homoeostasis by interrupting methyl addition to C-24 thereby impairing growth
24(R,S)-25-epiminolanosterol
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24(S)-24-methyl-25-thiacholest-5-enol iodide
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24beta-aminolanosterol
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25-aza-24,25-dihydrolanosterol
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25-Aza-24,25-dihydrozymosterol
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25-Azacholesterol hydrochloride
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25-thiacholesterol iodide
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25-thialanosterol iodide
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26,27-dehydrolanosterol
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26-nor-25-thialanosterol
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30-amino-24,25-dihydrolanosterol
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4-(3S,20R)-[(E)-2-(3-hydroxypregn-7-en-20-yl)-ethenyl]-1-methylpyridinium iodide
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5'-deoxy-5'-(methylthio)adenosine
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AdoMet analog, competitive inhibitor
7-amino-24,25-dihydrolanosterol
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amphotericine B
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inhibits the wild-type at concentrations above 60 nM, inhibition can be hindered by zymosterol
cholesta-8,24(28)-dienol
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ergosta-5,7,22-trienol
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Filipin
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slightly inhibiting at low concentration
methyl ([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)acetate
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methyl 3-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)propanoate
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methyl 4-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)butanoate
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methyl 5-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)pentanoate
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methyl 6-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)hexanoate
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methyl 7-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)heptanoate
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methyl 8-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)octanoate
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Nystatin
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slightly inhibiting at low concentration
S-adenosyl-L-homocysteine
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S-isobutyladenosine
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AdoMet analog, competitive inhibitor
sinefungin
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AdoMet analog, competitive inhibitor
Substrate analogues
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dead-end inhibitors
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22,26-azasterol
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23-Azacholesterol
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24(R,S),25-epiminolanosterol
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24(R,S),25-epiminolanosterol
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25-azalanosterol
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26,27-dehydrozymosterol
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26,27-dehydrozymosterol
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mechanism-based irreversible inhibition
26,27-dehydrozymosterol
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irreversible inhibitor that binds covalently to the SMT, affinitylabels the active site to convert to a product characterized as delta23(24)-sterol
26,27-dehydrozymosterol
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26,27-dehydrozymosterol
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desmosterol
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competitive versus sterol and S-adenosyl-L-methionine
desmosterol
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competitive versus sterol and S-adenosyl-L-methionine
ergosterol
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reversible inhibitor
ketoconazole
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Zymosterol
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competitive versus sterol and S-adenosyl-L-methionine
Zymosterol
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competitive versus sterol and S-adenosyl-L-methionine
additional information
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overview, diverse substrate and transition state analogues
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additional information
newly synthesized azasterols methyl ([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)acetate, methyl 3-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)propanoate, methyl 4-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)butanoate, methyl 5-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)pentanoate, methyl 6-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)hexanoate, methyl 7-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)heptanoate, and methyl 8-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)octanoate, none show any significant inhibition against the recombinant enzyme
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