Ligand guanosine 5'-monophosphate

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Basic Ligand Information

Molecular Structure
Picture of guanosine 5'-monophosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H14N5O8P
guanosine 5'-monophosphate
RQFCJASXJCIDSX-UUOKFMHZSA-N
Synonyms:
5'-GMP, acyclo-GMP, GMP, guanine ribose 5'-phosphate, guanosine 5'-phosphate, guanosine monophosphate, guanosine phosphate, guanylic acid
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for guanosine 5'-monophosphate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (43 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
GMP + [phosphate]n = GDP + [phosphate]n-1
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
diphosphate + guanosine = phosphate + GMP
show the reaction diagram
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ATP + guanosine = ADP + GMP
show the reaction diagram
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GDP + [phosphate]n = GMP + [phosphate]n+1
show the reaction diagram
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lactyl-2-diphospho-5'-guanosine + 7,8-didemethyl-8-hydroxy-5-deazariboflavin = guanosine 5'-phosphate + coenzyme F420-0
show the reaction diagram
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5'-phosphoguanylyl-(3',5')-guanosine + H2O = GMP + guanosine
show the reaction diagram
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3',5'-cGMP + H2O = 5'-GMP
show the reaction diagram
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5'-phosphoguanylyl-(3'->5')guanosine + H2O = 2 5'-GMP
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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GTP + H2O = GMP + diphosphate
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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GTP + RNA 3'-terminal-phosphate = GMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate
show the reaction diagram
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-
GTP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = GMP + diphosphate + (deoxyribonucleotide)n+m
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (108 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
GMP + trans-farnesyl diphosphate = CDP + trans-farnesyl triphosphate
show the reaction diagram
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ATP + GMP = ADP + GDP
show the reaction diagram
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ATP + GMP = ADP + GDP
show the reaction diagram
-
ATP + GMP = ADP + GDP
show the reaction diagram
-
GMP + [phosphate]n = GDP + [phosphate]n-1
show the reaction diagram
-
5'-GMP + H2O = guanosine + phosphate
show the reaction diagram
-
5'-GMP + H2O = guanosine + phosphate
show the reaction diagram
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GMP + H2O = guanosine + phosphate
show the reaction diagram
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5'-GMP + H2O = guanine + D-ribose 5-phosphate
show the reaction diagram
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GMP + H2O = XMP + NH3
show the reaction diagram
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GMP + H2O = ?
show the reaction diagram
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5'-GMP + H2O = guanosine + phosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (219 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
guanylyl sulfate + reduced methyl viologen = GMP + methyl viologen + sulfite
show the reaction diagram
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-
CMP-alpha-N-acetylneuraminate + NeuAc-alpha2,8-NeuAc-alpha2,3-Gal-beta1,4-Glc-beta-FCHASE = GMP + ?
show the reaction diagram
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-
AMP + guanosine = adenosine + guanosine 5'-phosphate
show the reaction diagram
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-
D-fructose 6-phosphate + GDP = D-fructose 1,6-bisphosphate + GMP
show the reaction diagram
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-
GDP + D-glucose = GMP + D-glucose 6-phosphate
show the reaction diagram
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GDP + adenosine = GMP + AMP
show the reaction diagram
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-
ATP + guanosine = ADP + GMP
show the reaction diagram
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GDP + casein = GMP + phosphorylated casein
show the reaction diagram
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GDP + trans-farnesyl diphosphate = GMP + trans-farnesyl triphosphate
show the reaction diagram
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-
GDP + [phosphate]n = GMP + [phosphate]n+1
show the reaction diagram
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GTP + D-ribose 5-phosphate = GMP + 5-phospho-alpha-D-ribose 1-diphosphate
show the reaction diagram
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GTP + thiamine = GMP + thiamine diphosphate
show the reaction diagram
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lactyl-2-diphospho-5'-guanosine + 7,8-didemethyl-8-hydroxy-5-deazariboflavin = guanosine 5'-phosphate + coenzyme F420-0
show the reaction diagram
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-
guanosine-5'-diphospho-5'-[DNA] + H2O = phospho-5'-[DNA] + GMP
show the reaction diagram
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[DNA]-3'-diphospho-5'-guanosine + H2O = [DNA]-3'-phosphate + GMP
show the reaction diagram
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poly(G) = 5'-GMP
show the reaction diagram
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-
GDP + H2O = GMP + phosphate
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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5'-GDP + H2O = GMP + phosphate
show the reaction diagram
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guanosine 3',5'-bisphosphate + H2O = guanosine 5'-phosphate + phosphate
show the reaction diagram
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glucose + GDP = glucose 6-phosphate + GMP
show the reaction diagram
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polyguanylic acid + H2O = 5'-GMP + 5'-phosphooligonucleotides
show the reaction diagram
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cyclic 3',5'-GMP + H2O = 5'-GMP
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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GDP-Man + H2O = Man-1-phosphate + GMP
show the reaction diagram
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guanosine 5'-p-nitrophenylphosphate + H2O = p-nitrophenol + GMP
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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-
GDP + H2O = GMP + phosphate
show the reaction diagram
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-
GTP + H2O = GMP + diphosphate
show the reaction diagram
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GDP + H2O = GMP + phosphate
show the reaction diagram
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GTP + L-aspartate + tRNAAsp = GMP + diphosphate + L-aspartyl-tRNAAsp
show the reaction diagram
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GTP + L-phenylalanine + tRNAPhe = GMP + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
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GTP + acetate + CoA = GMP + diphosphate + acetyl-CoA
show the reaction diagram
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GTP + ferulate + CoA = GMP + diphosphate + feruloyl-CoA
show the reaction diagram
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GTP + 3-hydroxypropionate + CoA + NADPH = GMP + diphosphate + NADP+ + propionyl-CoA
show the reaction diagram
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GTP + acetate + citrate (pro-3S)-lyase = GMP + diphosphate + citrate(pro-3S)-lyase
show the reaction diagram
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GTP + phytanate + CoA = GMP + diphosphate + phytanoyl-CoA
show the reaction diagram
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GTP + o-succinylbenzoate + CoA = GMP + diphosphate + o-succinylbenzoyl-CoA
show the reaction diagram
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GTP + oxalate + CoA = GMP + diphosphate + oxalyl-CoA
show the reaction diagram
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GTP + (R)-pantoate + beta-alanine = GMP + diphosphate + (R)-pantothenate
show the reaction diagram
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GTP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxyltransferase] = GMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxyltransferase]
show the reaction diagram
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GTP + L-Asp + L-Gln = GMP + diphosphate + Asn + Glu
show the reaction diagram
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acetone + CO2 + GTP + H2O = acetoacetate + GMP + phosphate
show the reaction diagram
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GTP + RNA 3'-terminal-phosphate = GMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate
show the reaction diagram
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GTP + RNA 3'-terminal-phosphate = GMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate
show the reaction diagram
-
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GTP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = GMP + diphosphate + (deoxyribonucleotide)n+m
show the reaction diagram
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GTP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = GMP + diphosphate + (deoxyribonucleotide)n+m
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (7 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enhances activity
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activation
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stimulates
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enhances activity
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Activator in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
GMP (0.25 mM) is a strong activator
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ascites tumour cells
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activates 2-oxoglutarate dehydrogenase complex
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slight stimulation
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activation, about 35% as efficient as AMP
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1 mM, activity: 104%, isoenzyme 1; 1 mM, activity: 168%, isoenzyme 2
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substrate GMP acting as an activator, partitioning between the allosteric and active site, is the basis for the sigmoidicity of the initial velocity versus GMP concentration plot
2',3'-cyclic nucleotide phosphodiesterase activity
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approx. 10fold activation of dephosporylated ODC at 1 mM, approx. 1.2fold activation of native ODC
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slight activation
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Inhibitor in Enzyme-catalyzed Reactions (331 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
at low levels of Ca2
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0.02 mM, 30% inhibition; 2 mM, 30% inhibition
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50% inhibition at 0.094 mM
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10 mM, almost complete inhibition
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competitive with respect to GDP-fucose
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competitive versus dGMP
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as strong as CMP
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weak inhibition
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1 mM, 20% inhibition
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erythrocytic kinase, kinetics
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0.4 mM, 50% inhibition
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1 mM, complete inhibition of enzymic reaction with tRNA
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20 mM, 64% inhibition
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inhibits uridylyl removing activity
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slight
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little effect
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1 mM: 5% inhibition
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0.5 mM: 70% inhibition
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purine monophosphate (RMP) and diphosphate nucleotides (RDP) exhibit competitive inhibition, furthermore PARN does not discriminate whether there is ribose or deoxyribose in the nucleotides, Mg2+ releases the inhibition by RDPs and RTPs, but not by RMPs
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42.7% inhibition at 10 mM
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uncompetitive inhibitor
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1 mM, 31% residual activity
substrate inhibition above 1 mM
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decreased IMP cyclohydrolase activity by 10-50%
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more than 40% inhibition of GTP cyclohydrolase activity
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included along with 2 mM GTP in the incubation mixture. 43% inhibition
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18% inhibition at 0.1 mM
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complete inhibition at 0.5 mM
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competitive inhibition with Ki: 0.001 mM
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90% inhibition
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25% inhibition at 67 mM
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weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (79 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (30 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2.7
-
pH 7.5, 85C
35
-
recombinant PAP, pH 8.0, 37C
3.33
-
synthesis of a copolymer of guanylic acid
244
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at pH 5.0 and 20C
11
-
+/- 0.87
11
-
+/- 0.87

KM Value (100 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.06
-
-
18.5
-
pH 7.5, 85C
4.4
-
recombinant PAP, pH 8.0, 37C
0.26
-
+/- 0.05
0.909
-
-
0.26
-
+/- 0.05
0.0112
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-

Ki Value (52 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0227
-
24C, pH 8.0
0.7
-
-
0.235
-
-
0.086
0.35
-
0.02
-
pH 7.5, 37C, recombinant wild-type enzyme, versus dGMP
8.7
-
pH 6.8, 25C
4.5
-
at pH 7.0, 30C
0.0283
-
pH 8.5, 37C
0.015
-
pH 6.0, 37C, recombinant GST-tagged enzyme
0.00479
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at pH 7.4 and 25C
0.229
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pH 8.5, 37C
0.001
-
competitive inhibition
0.022
-
-
0.1864
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in Tris-HCl (50 mM, pH 7.4), temperature not specified in the publication
0.000067
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wild-type, pH 6.0

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
7.9
-
IC50: 7.9 mM

References & Links