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(+/-)-cis/trans-Chrysanthemyl diphosphate
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-
(+/-)-cis/trans-Chrysanthemyl monophosphate
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-
(2Z)-3-methylhept-2-en-1-yl trihydrogen diphosphate
(2Z)-3-methylhex-2-en-1-yl trihydrogen diphosphate
(2Z)-3-methyloct-2-en-1-yl trihydrogen diphosphate
(E/Z)-3-cyclopropyl-2-buten-1-yl diphosphate
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-
(N,N-dimethylamino)-1-ethyl diphosphate
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transition state analogue
(Z)-3-difluoromethyl-2-buten-1-yl diphosphate
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reversible
(Z)-3-fluoromethyl-2-buten-1-yl diphosphate
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reversible
(Z)-4-Fluoro-3-methyl-2-buten-1-yl diphosphate
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inactivates through an active-site-directed covalent modification
2,2-Diphenyl-1-(beta-dimethylaminoethoxy)pentane hydrochloride
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-
2,3-butadien-1-yl diphosphate
2,3-cis,6,7-trans-farnesyl diphosphate
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-
2-(dimethylamino)ethyl diphosphate
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weak competitive inhibitor
2-(dimethylamino)ethyl phosphate
2-[ethyl(methyl)amino]ethyl trihydrogen diphosphate
2-[ethyl(propyl)amino]ethyl trihydrogen diphosphate
3,4-Epoxy-1-butenyl diphosphate
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active-site directed irreversible inhibitor
3,4-epoxy-3-methyl-1-butyl diphosphate
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-
3,4-epoxy-3-methylbutyl diphosphate
3,4-oxido-3-methyl-1-butyl diphosphate
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inactivation through formation of covalent adducts with the reduced flavin, modification of the isoalloxazine ring at position N5
3-(Fluoromethyl)-3-buten-1-yl diphosphate
3-Bromo-3-butenyl diphosphate
-
competitive
3-cyclopropyl-3-buten-1-yl diphosphate
3-cyclopropylbut-3-en-1-yl trihydrogen diphosphate
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cyclopropyl-derivative of isopentenyl diphosphate, mechanism-based inhibitor
3-Methyl-3,4-epoxybutyl diphosphate
3-methyl-5-oxo-hexyl diphosphate
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-
3-methyl-5-oxo-hexyl diphosphate ethylene glycol acetal
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-
3-methylene-4-penten-1-yl diphosphate
3-oxiran-2-ylbut-3-en-1-yl trihydrogen diphosphate
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epoxy-derivative of isopentenyl diphosphate, mechanism-based inhibitor. The enzyme catalyzes formation of a stable covalent adduct between the inhibitor and FMNH2 in a reaction catalyzed by protonation of the epoxide moiety followed by nucleophilic addition of the cofactor
3-oxiranyl-3-buten-1-yl diphosphate
4-aminophenyl-2-ethane-1,1-bisphosphonic acid
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weak. Due to inhibition of more than one enzyme in the mevalonate pathway may lead to an increase in antiresorptive potency compared to bisphosphonates that only inhibit farnesyl diphosphate synthase
beta-Diethylaminoethyldiphenylpropylacetate hydrochloride
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i.e. SKF-525A
dimethylallyl diphosphate
Dimethylallyl diphosphate containing fluorine, epoxy, and ammonium function groups
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-
-
dimethylammonium diphosphate
EDTA
addditon of 5mM EDTA results in almost complete loss of activity
epoxide of isopentenyl diphosphate
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-
geranyl monophosphate
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-
homodimethylallyl diphosphate
homoisopentenyl diphosphate
Isoamyl diphosphate
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competitive
Isopentenyl diphosphates containing fluorine, epoxy, and ammonium functional groups
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-
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linaloyl monophosphate
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-
Methyl diphosphate
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competitive
Mg2+
Cinchona robusta
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isomerase I is activated by concentrations below 1 mM of Mn2+ or Mg2+, increasing concentrations are inhibitory
N,N-dimethyl-2-amino-1-ethyl diphosphate
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transition state analogue, competitive
N,N-dimethylaminoethyl diphosphate
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-
O2
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the overall reaction is sensitive to O2
p-hydroxymercuribenzoate
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-
Terpene diphosphate esters
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-
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Terpene monophosphate esters
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-
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additional information
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not inhibited by 2-[ethyl(propyl)amino]ethyl trihydrogen diphosphate
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(2Z)-3-methylhept-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methylhept-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methylhept-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methylhex-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methylhex-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methylhex-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methyloct-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methyloct-2-en-1-yl trihydrogen diphosphate
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-
(2Z)-3-methyloct-2-en-1-yl trihydrogen diphosphate
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-
2,3-butadien-1-yl diphosphate
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competitive inhibitor
2,3-butadien-1-yl diphosphate
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competitive inhibitor
2-(dimethylamino)ethyl phosphate
Cinchona robusta
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-
2-(dimethylamino)ethyl phosphate
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may function as a transition state or reactive intermediate analogue of a carbocation that binds extremely tightly
2-(dimethylamino)ethyl phosphate
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competitive
2-[ethyl(methyl)amino]ethyl trihydrogen diphosphate
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-
2-[ethyl(methyl)amino]ethyl trihydrogen diphosphate
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-
2-[ethyl(methyl)amino]ethyl trihydrogen diphosphate
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-
2-[ethyl(propyl)amino]ethyl trihydrogen diphosphate
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-
2-[ethyl(propyl)amino]ethyl trihydrogen diphosphate
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-
3,4-epoxy-3-methylbutyl diphosphate
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i.e. EIPP, mechanism-based inhibitor of type I enzyme, covalent modification of reduced FMN in N5 position
3,4-epoxy-3-methylbutyl diphosphate
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irreversible inhibition
3-(Fluoromethyl)-3-buten-1-yl diphosphate
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-
3-(Fluoromethyl)-3-buten-1-yl diphosphate
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inactivates through an active-site-directed covalent modification
3-(Fluoromethyl)-3-buten-1-yl diphosphate
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active site-directed inhibitor
3-(Fluoromethyl)-3-buten-1-yl diphosphate
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active site-directed inhibitor; irreversible
3-(Fluoromethyl)-3-buten-1-yl diphosphate
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inactivation through formation of covalent adducts with the reduced flavin
3-butyn-1-yl diphosphate
-
competitive inhibitor
3-butyn-1-yl diphosphate
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competitive inhibitor
3-cyclopropyl-3-buten-1-yl diphosphate
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reversible
3-cyclopropyl-3-buten-1-yl diphosphate
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-
3-Methyl-3,4-epoxybutyl diphosphate
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-
3-Methyl-3,4-epoxybutyl diphosphate
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time-dependent first-order loss of activity
3-methylene-4-penten-1-yl diphosphate
irreversible inhibition; the covalent adduct formed between irreversible mechanism based inhibitors, 3-methylene-4-penten-1-yl diphosphate or 3-oxiranyl-3-buten-1-yl diphosphate, and the flavin cofactor are investigated by X-ray crystallography and UV-visible spectroscopy. Both the crystal structures of enzyme binding the flavin-inhibitor adduct and the UV-visible spectra of the adducts indicate that the covalent bond is formed at C4a of flavin rather than at N5
3-methylene-4-penten-1-yl diphosphate
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inactivation through formation of covalent adducts with the reduced flavin
3-oxiranyl-3-buten-1-yl diphosphate
irreversible inhibition; the covalent adduct formed between irreversible mechanism based inhibitors, 3-methylene-4-penten-1-yl diphosphate or 3-oxiranyl-3-buten-1-yl diphosphate, and the flavin cofactor are investigated by X-ray crystallography and UV-visible spectroscopy. Both the crystal structures of enzyme binding the flavin-inhibitor adduct and the UV-visible spectra of the adducts indicate that the covalent bond is formed at C4a of flavin rather than at N5
3-oxiranyl-3-buten-1-yl diphosphate
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irreversible
dimethylallyl diphosphate
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-
dimethylallyl diphosphate
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-
dimethylallyl diphosphate
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-
dimethylallyl diphosphate
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-
dimethylallyl diphosphate
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-
dimethylammonium diphosphate
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dimethylammonium diphosphate
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dimethylammonium diphosphate
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diphosphate
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-
diphosphate
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inhibitory effect decreases in the order of isomerases I, II, III, and IV
farnesyl diphosphate
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FMN
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geranyl diphosphate
Cinchona robusta
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-
homodimethylallyl diphosphate
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-
homodimethylallyl diphosphate
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-
homodimethylallyl diphosphate
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-
homoisopentenyl diphosphate
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-
homoisopentenyl diphosphate
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-
homoisopentenyl diphosphate
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-
iodoacetamide
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70% inhibition at 0.001 mM, complete inhibition at 0.1 mM
iodoacetamide
Cucurbita sp.
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-
iodoacetamide
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inhibitory effect decreases in the order of isomerases I, II, III, no inhibition of isomerase IV
iodoacetic acid
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-
isopentenyl diphosphate
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-
isopentenyl diphosphate
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Mn2+
Cinchona robusta
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isomerase I is activated by concentrations below 1 mM of Mn2+ or Mg2+, increasing concentrations are inhibitory
Mn2+
inhibitory at high concentrations