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Information on EC 4.6.1.12 - 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
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4.6.1.12 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseIUBMB Comments
The enzyme from Escherichia coli requires Mg2+ or Mn2+. Forms part of an alternative nonmevalonate pathway for terpenoid biosynthesis (for diagram, click here).
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Word Map
- 4.6.1.12
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electrolysis
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salivary
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mucoepidermoid
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myoepithelial
- milk
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wastewater
-
anode
-
cathode
-
microvascular
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adenoid
- mastitis
- geobacter
- calponin
- stat5
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bioelectrochemical
- caspofungin
-
coulomb
-
single-chamber
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biocathode
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electroactive
-
warthin
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methanogenesis
- posaconazole
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syntrophic
-
echinocandins
- voriconazole
- micafungin
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intermediate-grade
- anidulafungin
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bioanode
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pnecs
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biohydrogen
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hydrogenotrophic
- drug development
- synthesis
- analysis
- medicine
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
mecs, mecps, ispdf, 2-c-methyl-d-erythritol 2,4-cyclodiphosphate synthase, 2c-methyl-d-erythritol 2,4-cyclodiphosphate synthase, 2c-methyl-d-erythritol-2,4-cyclodiphosphate synthase, 2-methylerythritol 2,4-cyclodiphosphate synthase, ygbb protein, mec synthase, 2-c-methyl-d-erythritol-2,4-cyclodiphosphate synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
2-methylerythritol 2,4-cyclodiphosphate synthase
IspDF
IspF
MDS
ME-CPP synthase
MECDP synthase
MECDP-synthase
MECP
MECPS
MECS
YGBB
IspDF
-
bifunctional methylerythritol 4-phosphate cytidyltransferase methylerythritol 2,4-cyclodidiphosphate synthase. Complex formation of IspDF with 4-diphosphocytidyl-2C-methyl-D-erythritol kinase is observed in solution
IspDF
-
bifunctional methylerythritol 4-phosphate cytidyltransferase methylerythritol 2,4-cyclodidiphosphate synthase.Complex formation of IspDF with 4-diphosphocytidyl-2C-methyl-D-erythritol kinase is observed in solution
MECDP-synthase
-
-
-
-
MECPS
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
The enzyme from Escherichia coli requires Mg2+ or Mn2+. Forms part of an alternative nonmevalonate pathway for terpenoid biosynthesis
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CMP-lyase (cyclizing; 2-C-methyl-D-erythritol 2,4-cyclodiphosphate-forming)
The enzyme from Escherichia coli requires Mg2+ or Mn2+. Forms part of an alternative nonmevalonate pathway for terpenoid biosynthesis (for diagram, click here).
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CAS REGISTRY NUMBER
COMMENTARY
287480-92-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
4-diphosphocytidyl-2C-methyl-D-erythritol
2C-methyl-D-erythritol 3,4-cyclophosphate + CMP
at low rate
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
involved in mevalonate-independent biosynthesis of isoprenoids
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
at low rate
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
nonmevalonate pathway of isoprenoid biosynthesis
-
-
?
additional information
?
-
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bifunctional 4-diphosphocytidyl-2C-methyl-D-erythritol synthase/2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase enzyme associates in solution with 4-diphosphocytidyl-2C-methyl-D-erythritol kinase, i.e. ispE protein. No evidence for substrate channeling during the three enzymes subsequent catalytic reactions
-
-
?
additional information
?
-
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depletion of MEC synthase has an early and significant impact on cell wall biosynthesis and leads ultimately to cell death
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-
?
additional information
?
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active site including CDP-binding sites (Asp140Gly142 and Leu184Leu189Ser190Lys216Thr217Glu219). Owns a 60 amino-acid plastidial transit peptide at its N-terminus
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol
2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP
nonmevalonate pathway of isoprenoid biosynthesis
-
-
?
additional information
?
-
-
depletion of MEC synthase has an early and significant impact on cell wall biosynthesis and leads ultimately to cell death
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
involved in mevalonate-independent biosynthesis of isoprenoids
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
-
?
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
Na+
-
presence of tetrahedral Zn2+ in one of the metal-binding sites and an octahedral sodium ion in the second metal site in absence of substrate
Zinc
-
tightly binds one zinc ion per subunit of the trimer at the active site, which helps to position the substrate for direct attack of the 2-phosphate group on the beta-phosphate
Zn2+
additional information
the tetrahedrally arranged transition metal binding site, potentially occupied by Mn2+, sits at the base of the active site cleft. A phosphate oxygen of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate and the side chains of Asp8, His10, and His42 occupy the metal side chains of Asp8, His10, and His42 occupy the metal side coordination sphere
Mg2+
Mg2+ or Mn2+, positioned between the alpha- and beta-phosphates of the substrate, acts in concert with the Zn2+ to align and polarize the substrate for catalysis
Mn2+
a Mn2+ with octahedral geometry, is positioned between the alpha and beta phosphates acting in concert with the Zn2+ to align and polarize the substrate for catalysis
Mn2+
Mg2+ or Mn2+, positioned between the alpha- and beta-phosphates of the substrate, acts in concert with the Zn2+ to align and polarize the substrate for catalysis
Zn2+
Zn2+-binding site, addition of a Zn2+-binding moiety may prove valuable in assisting the design of potent and selective inhibitors
Zn2+
-
presence of tetrahedral Zn2+ in one of the metal-binding sites and an octahedral sodium ion in the second metal site in absence of substrate
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
2-amino-N-hydroxy-3-(1-H-indol-3-yl)-propionimidic acid
highest affinity of all the ligands examined, due to Zn2+-hydroxamate coordination, KD value of 0.0019 mM
4-amino-1-[(2S,3aS,4S,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidin-2(1H)-one
KD value of 20.5 mM
4-amino-1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]pyrimidin-2(1H)-one
KD value of 0.925 mM
EDTA
5 mM. Activity can be restored by the addition of Mg2+ to a concentration of 10 mM
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)-4-chlorobenzamide
1 mM, 52% inhibition
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)benzamide
1 mM, 59% inhibition
N-[4-[(6-aminopyridin-3-yl)amino]-3-methylbenzyl]-4-(trifluoromethyl)benzamide
1 mM, 60% inhibition
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
-
additional information
5-(1,3-benzodioxol-5-ylamino)-5-oxopentanoic acid, 2-[(2,6-diaminopyrimidin-4-yl)sulfanyl]acetamide and 4-(5-amino-1,3,4-oxadiazol-2-yl)-1,2,5-oxadiazol-3-amine are inactive. Activity with compounds 2-amino-N-hydroxy-acetimidic acid, N-hydroxy-nicotinimidic acid, 5-bromo-thiophene-2-sulfonic acid amide, 4-bromobenzenesulfonamide and 4-(4-dimethylamino-phenylazo)-benzenesulfonamide are not measurable
-
additional information
-
5-(1,3-benzodioxol-5-ylamino)-5-oxopentanoic acid, 2-[(2,6-diaminopyrimidin-4-yl)sulfanyl]acetamide and 4-(5-amino-1,3,4-oxadiazol-2-yl)-1,2,5-oxadiazol-3-amine are inactive. Activity with compounds 2-amino-N-hydroxy-acetimidic acid, N-hydroxy-nicotinimidic acid, 5-bromo-thiophene-2-sulfonic acid amide, 4-bromobenzenesulfonamide and 4-(4-dimethylamino-phenylazo)-benzenesulfonamide are not measurable
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.483
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
-
2
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.8
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
-
2.5
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
-
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0089 - 0.06
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.02 - 0.192
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
0.018 - 0.223
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
0.002 - 0.069
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0176 - 0.3
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
0.0015 - 0.018
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0015 - 0.032
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.089 - 0.322
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0016 - 0.212
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0032 - 0.3
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0028 - 0.3
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.3
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
0.0039 - 0.058
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0019 - 0.036
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.0063 - 0.3
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
0.015 - 0.039
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
0.000007
artesunate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.000013
Chloroquine
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.54
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)-4-chlorobenzamide
Escherichia coli
-
0.45
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)benzamide
Escherichia coli
-
0.49
N-[4-[(6-aminopyridin-3-yl)amino]-3-methylbenzyl]-4-(trifluoromethyl)benzamide
Escherichia coli
-
0.0089
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.014
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.032
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.06
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.02
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.056
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.065
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.069
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.192
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.018
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.077
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.087
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Plasmodium falciparum
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.141
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.223
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
Escherichia coli
-
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.002
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum
inhibition of strains NF54 as measured by red blood cell assay
0.0021
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Mycobacterium tuberculosis
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.012
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Arabidopsis thaliana
photometric assay, in 100 mm Tris-HCl buffer, pH 8.0, 0.4 mM NADH, 1 mM ATP, 1 mM phosphoenolpyruvate, 10 mM MgCl2, 0.02 U of IspF protein, 0.5 U of CMP kinase, 0.5 U of pyruvate kinase, and 0.5 U of lactate dehydrogenase, at 22°C
0.035
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
Plasmodium falciparum