4.2.3.6 (7R)-(E)-6,7-dihydrofarnesyl diphosphate - 46050 4.2.3.6 (7S)-(E)-6,7-dihydrofarnesyl diphosphate modestly competitive 46051 4.2.3.6 1-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]proline 40.3% inhibition at 0.0187 mM 226157 4.2.3.6 10-cyclopropylidene farnesyl diphosphate mechanism-based inhibitor 52178 4.2.3.6 10-fluorofarnesyl diphosphate - 52179 4.2.3.6 2-([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)-N-[2-(4-hydroxyphenyl)ethyl]acetamide 45% inhibition at 0.0187 mM 226163 4.2.3.6 3-(1H-indol-2-yl)-N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]alanine 67.8% inhibition at 0.0187 mM 226161 4.2.3.6 3-phenyl-4-[2-([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamido]butanoic acid 26.7% inhibition at 0.0187 mM 226172 4.2.3.6 4-[2-([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamido]-3-phenylbutanoic acid 12.2% inhibition at 0.0187 mM 226167 4.2.3.6 benzyl triethylammonium cation BTAC alone does not inhibit the trichodiene synthase, 5-30 microM acts as a competitive inhibitor in the presence of 5-20 microM PPi 139250 4.2.3.6 beta-hydroxy-N-[([(Z)-[(3Z,17alpha)-17-hydroxypregn-4-en-20-yn-3-ylidene]amino]oxy)acetyl]phenylalanine 21.1% inhibition at 0.0187 mM 226173 4.2.3.6 diphosphate PPi 17 4.2.3.6 ethyl beta-hydroxy-N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate 25.3% inhibition at 0.0187 mM 226166 4.2.3.6 farnesyl diphosphate analogs - 47225 4.2.3.6 farnesyl diphosphate analogs 10-fluorofarnesyl diphosphate is the most effective competitive inhibitor 47225 4.2.3.6 methyl 1-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]prolinate 70.5% inhibition at 0.0187 mM 226158 4.2.3.6 methyl N-[([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate 21.6% inhibition at 0.0187 mM 226170 4.2.3.6 methyl N-[([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]tyrosinate 22.6% inhibition at 0.0187 mM 226171 4.2.3.6 methyl N-[([(Z)-[(3Z)-17-hydroxyandrost-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate 53.2% inhibition at 0.0187 mM 226169 4.2.3.6 methyl N-[([(Z)-[(3Z)-17-hydroxypregn-4-en-20-yn-3-ylidene]amino]oxy)acetyl]phenylalaninate 66.3% inhibition at 0.0187 mM 226174 4.2.3.6 Mn2+ 0.01 mM, can partially replace Mg2+, inhibition at higher concentration 11 4.2.3.6 additional information identification of active site residues by site-directed mutagenesis 2 4.2.3.6 N-[(3,4-dihydroxyphenyl)methyl]-2-([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamide 70.6% inhibition at 0.0187 mM 226159 4.2.3.6 N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]-3-(1H-indol-2-yl)alanine 61.8% inhibition at 0.0187 mM 226162 4.2.3.6 N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]glycine 59.5% inhibition at 0.0187 mM 226165 4.2.3.6 N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]valine 49% inhibition at 0.0187 mM 226164 4.2.3.6 N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]isoleucine 54.8% inhibition at 0.0187 mM 226160 4.2.3.6 N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalanine 39% inhibition at 0.0187 mM 226154 4.2.3.6 N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]serine 44.5% inhibition at 0.0187 mM 226156 4.2.3.6 N-[2-(4-hydroxyphenyl)ethyl]-2-([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamide 58.4% inhibition at 0.0187 mM 226155 4.2.3.6 N2-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]asparagine 54.3% inhibition at 0.0187 mM 226168 4.2.3.6 NPD10133 - 228176 4.2.3.6 NPD10137 - 228179 4.2.3.6 NPD10138 - 228180 4.2.3.6 NPD10465 - 228181 4.2.3.6 NPD10467 - 228188 4.2.3.6 NPD10474 - 228189 4.2.3.6 NPD10852 - 228190 4.2.3.6 NPD11144 - 228182 4.2.3.6 NPD1260 - 228186 4.2.3.6 NPD13120 - 228183 4.2.3.6 NPD1356 - 228187 4.2.3.6 NPD2161 - 228192 4.2.3.6 NPD2246 - 228193 4.2.3.6 NPD2364 - 228194 4.2.3.6 NPD3 - 228177 4.2.3.6 NPD3187 - 228178 4.2.3.6 NPD352 - 228191 4.2.3.6 NPD520 - 228184 4.2.3.6 NPD553 - 228185