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Information on EC 1.3.1.98 - UDP-N-acetylmuramate dehydrogenase
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EC Tree
1.3.1.98 UDP-N-acetylmuramate dehydrogenaseIUBMB Comments
A flavoprotein (FAD). NADH can to a lesser extent replace NADPH.
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
udp-n-acetylenolpyruvylglucosamine reductase, udp-n-acetylenolpyruvoylglucosamine reductase, murbab, udp-n-acetylenolpyruvyl glucosamine reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alr5066
EC 1.1.1.158
MurB
reductase, uridine diphosphoacetylpyruvoylglucosamine
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UDP-GlcNAc-enoylpyruvate reductase
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UDP-N-acetylenolpyruvoylglucosamine reductase
UDP-N-acetylenolpyruvyl glucosamine reductase
UDP-N-acetylenolpyruvylglucosamine reductase
UDP-N-acetylglucosamine-enoylpyruvate reductase
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UDP-N-acetylmuramate dehydrogenase
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uridine diphospho-N-acetylglucosamine-enolpyruvate reductase
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uridine-5'-diphospho-N-acetyl-2-amino-2-deoxy-3-O-lactylglucose:NADP-oxidoreductase
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additional information
a type II enzyme lacking Tyr loop and split betaalphabetabeta fold
UDP-N-acetylenolpyruvoylglucosamine reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
ping pong mechanism, contains FAD
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UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
reaction mechanism, detailed scheme of the second half
UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
the nicotinamide ring of NADP+ stacks against the si face of the isoalloxazine ring of FAD, suggesting an unusual mode of hydride transfer to flavin. Both substrates share the binding site located between two lobes of the substrate-binding domain III, consistent with a ping pong mechanism with sequential substrate binding, structural analysis of the first half-reaction, overview
UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
ping pong mechanism, contains FAD
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UDP-N-acetyl-alpha-D-muramate + NADP+ = UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-alpha-D-muramate:NADP+ oxidoreductase
A flavoprotein (FAD). NADH can to a lesser extent replace NADPH.
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CAS REGISTRY NUMBER
COMMENTARY
39307-28-3
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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
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
structural analysis of the first half-reaction, hydride transfer from NADPH to FAD using the crystal structure of the enzyme in ternary complex with FAD and NADP+, overview. Enzyme MurB is a type I UNAGEP reductase
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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the enzyme MurB catalyzes the reduction of the enolpyruvyl moiety of UDP-GlcNAc-enolpyruvate to lactyl ether to produce UDP-N-acetylmuramic acid
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
essential for cell growth, functions in bacterial peptidoglycan biosynthesis
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetylmuramate + NADP+
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r
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetylmuramate + NADP+
i.e. enolpyruvyl-UDP-N-acetylglucosamine
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r
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
complex of MurB and substrate forms strong hydrogen bond with Arg176, Ser257 and Glu361. The secondary structure of MurB consists of 13 helices, 6 beta sheets, 6 beta hairpins, 5 beta bluges, 19 stands, 52 beta turns and 4 inverse gamma turns
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UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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biosynthetic MurB pathway, overview
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
residues Arg213, Arg176, His259, Asn71, Tyr175, Ser226, and Glu296 are involved in catalysis
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
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?
additional information
?
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enzyme catalyzes one of the cytoplasmic steps of E. coli peptidoglycan synthesis
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?
additional information
?
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enzyme catalyzes one of the cytoplasmic steps of E. coli peptidoglycan synthesis
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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
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetylmuramate + NADP+
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r
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine + NADPH + H+
UDP-N-acetyl-alpha-D-muramate + NADP+
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the enzyme MurB catalyzes the reduction of the enolpyruvyl moiety of UDP-GlcNAc-enolpyruvate to lactyl ether to produce UDP-N-acetylmuramic acid
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
essential for cell growth, functions in bacterial peptidoglycan biosynthesis
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH
UDP-N-acetyl-3-D-muramate + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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biosynthetic MurB pathway, overview
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
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?
UDP-N-acetylenolpyruvylglucosamine + NADPH + H+
UDP-N-acetylmuramic acid + NADP+
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?
additional information
?
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enzyme catalyzes one of the cytoplasmic steps of E. coli peptidoglycan synthesis
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?
additional information
?
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enzyme catalyzes one of the cytoplasmic steps of E. coli peptidoglycan synthesis
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
nicotinamide hypoxanthine dinucleotide phosphate
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reduced form, active substrate
FAD
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prosthetic group: FAD, Na2S2O4, NaBH4 and to a lesser extent NADH can replace NADPH
NADPH
binding structure, overview. Hydride transfer occurs via the isoalloxazine si face
additional information
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absorption spectra not consistent with flavoprotein
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additional information
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thio-NADH, nicotinamide hyopxanthine dinucleotide in reduced form not substrates
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Cs+
K+
Na+
NH4+
Rb+
Tl+
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affinity about 8 times greater than K+, activation in decreasing order: Tl+, K+, NH4+, Rb+, Li+, Na+
additional information
Cs+
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at saturating cation concentration maximal enzyme activity: 2 units/mg
K+
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at saturating cation concentration maximal enzyme activity: 50 units/mg
K+
PaMurB crystal structure contains a potassium ion in the active site. The potassium ion displays a pentagonal bipyramidal coordination geometry with two main chain oxygen atoms (Ala237, Ser239), one side chain carboxyl oxygen atom from Glu-335, one side chain oxygen atom of Asn-57 and the O7n oxygen atom of the nicotinamide ring as ligands. The potassium ion activates MurB by facilitating substrate orientation and binding
Na+
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at saturating cation concentration maximal enzyme activity: 5 units/mg
NH4+
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at saturating cation concentration maximal enzyme activity: 35 units/mg
Rb+
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at saturating cation concentration maximal enzyme activity: 33 units/mg
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(4S)-1,2-bis(4-chlorophenyl)-5-[2-(2,4-difluorophenyl)-2-oxoethoxy]-4-methylpyrazolidin-3-one
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1,2-bis(3,4-dichlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (3,4-dichlorophenyl)amide
1,2-bis(3,4-dichlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid 4-tolylamide
1,2-bis(3-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-trifluoromethylphenyl)amide
1,2-bis(4-chlorophenyl)-4,4-bis(6-phenylhexyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4,4-bis[2-(2,4-difluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(2,4-dichlorobenzyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(2-ethylbutyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(2-phenylethyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(3-methoxybenzyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(3-oxo-3-phenylpropyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(3-phenylpropyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(4-oxo-4-phenylbutyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(4-phenylbutyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(5-phenylpentyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-(6-phenylhexyl)pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-[2-(2,4-difluorophenyl)-2-oxoethyl]-4-methylpyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-[2-(4-fluorophenyl)-2-oxoethyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-[2-(diethylamino)ethyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-4-[3-(trifluoromethyl)benzyl]pyrazolidine-3,5-dione
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1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1-naphthalen-2-ylethyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2-chlorophenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (3-chlorophenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (3-trifluoromethylphenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-chlorophenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-cyanophenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-hydroxyphenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-methoxyphenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4-trifluoromethylphenyl)amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid 2,4-dichlorobenzylamide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid 2-chlorobenzylamide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid 3,4-dichlorobenzylamide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid cyclohexylamide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid phenethylamide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid [1-(4-bromophenyl)ethyl]amide
1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid [4(3-(dimethylamino)propylcarbamoyl)-phenyl]amide
3-acetylpyridine adenine dinucleotide phosphate
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oxidized form, competitive with respect to NADPH
4'-[[1,2-bis(4-chlorophenyl)-3,5-dioxopyrazolidin-4-yl]methyl]biphenyl-2-carbonitrile
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4,4-bis[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-(2-chlorobenzyl)-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carbonyl]aminobenzoic acid
4-[1,2-bis(4-chlorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carbonyl]aminobenzoic acid ethyl ester
4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)-4-methylpyrazolidine-3,5-dione
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4-[2-(benzyloxy)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[2-(benzylsulfanyl)ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[2-[benzyl(ethyl)amino]ethyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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4-[3,5-bis(trifluoromethyl)benzyl]-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione
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