Ligand 2'-deoxyadenosine 5'-monophosphate

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Basic Ligand Information

Molecular Structure
Picture of 2'-deoxyadenosine 5'-monophosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H14N5O6P
2'-deoxyadenosine 5'-monophosphate
KHWCHTKSEGGWEX-RRKCRQDMSA-N
Synonyms:
2'-dAMP, 2'-deoxy-5'-adenylic acid, 2'-deoxy-5'-AMP, 2'-deoxy-adenosine 5'-phosphate, 2'-deoxy-AMP, 2'-deoxyadenosine-5'-phosphate, 2'-deoxyadenosine 5'-phosphate, 2'-deoxyadenosine monophosphate, 2-dAMP, 2-deoxy-AMP, 5'-dAMP, 5'd-AMP, 5-Deoxyadenylic acid, dAMP, deoxyadenosine 5'-phosphate, deoxyadenosine monophosphate


Show all pahtways known for Show all BRENDA pathways known for 2'-deoxyadenosine 5'-monophosphate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + dAMP = ADP + dADP
show the reaction diagram
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ATP + dAMP = ADP + dADP
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + 2'-deoxyadenosine = ADP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
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dADP + H2O = dAMP + phosphate
show the reaction diagram
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dATP + acetate + CoA = dAMP + diphosphate + acetyl-CoA
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dATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = dAMP + diphosphate + (deoxyribonucleotide)m+n
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dAMP + sulfite + cytochrome c = deoxyadenylyl sulfate + ?
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5'-dAMP + thymidine = 5'-deoxyadenosine + TMP
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dAMP + (phosphate)n+1 = dADP + (phosphate)n
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dGTP + dAMP = dGDP + dADP
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ATP + dAMP = ADP + dADP
show the reaction diagram
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ATP + dAMP = ADP + dADP
show the reaction diagram
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ATP + dAMP = ADP + dADP
show the reaction diagram
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2'-deoxy-adenosine 5'-phosphate + trans-farnesyl diphosphate = 2'-deoxyadenosine + trans-farnesyl triphosphate
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ATP + dAMP = ADP + dADP
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GTP + dAMP = GDP + dADP
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ATP + dAMP = ADP + dADP
show the reaction diagram
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2'-dAMP + phosphoenolpyruvate + diphosphate = 2'-dATP + pyruvate + phosphate
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5'-dAMP + H2O = adenosine + phosphate
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5'-dAMP + H2O = deoxyadenosine + phosphate
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5'-dAMP + H2O = ?
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dAMP + H2O = dIMP + NH3
show the reaction diagram
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dAMP + H2O = dIMP + NH3
show the reaction diagram
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2'-dAMP + H2O = 2'-dIMP + NH3
show the reaction diagram
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5-deoxyadenylic acid + H2O = dIMP + NH3
show the reaction diagram
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deoxyadenosine monophosphate + H2O = deoxyinosine monophosphate + NH3
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Product in Enzyme-catalyzed Reactions (109 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-methyl-dAMP + 2-oxoglutarate + O2 = dAMP + formaldehyde + succinate + CO2
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ADP + 2-deoxyadenosine = AMP + dAMP
show the reaction diagram
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ATP + deoxyadenosine = ADP + dAMP
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ATP + 2'-deoxyadenosine = ADP + 2'-deoxyadenosine 5'-phosphate
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dATP + D-ribose 5-phosphate = dAMP + 5-phospho-alpha-D-ribose 1-diphosphate
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dATP + 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine = dAMP + 2-amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)pteridine
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dATP + GTP = dAMP + guanosine 3'-diphosphate 5'-triphosphate
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p-tRNAHis + dATP + GTP = pppGp-tRNAHis + dAMP + diphosphate
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poly(a)-ssDNA + H2O = 5'-dAMP
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2'-deoxyadenosine 3',5'-bisphosphate + H2O = 2'-deoxyadenosine 5'-phosphate + phosphate
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3',5'-cdAMP + H2O = 5'-dAMP
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dADP + H2O = dAMP + phosphate
show the reaction diagram
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2'-deoxyadenosine adenosine tetraphosphate + H2O = ATP + 2'-dAMP + 2'-dATP + AMP
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dADP + H2O = dAMP + phosphate
show the reaction diagram
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dADP + H2O = dAMP + phosphate
show the reaction diagram
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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dATP + H2O = dAMP + diphosphate
show the reaction diagram
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2'-deoxy-succino-AMP = 2'-deoxy-AMP + fumarate
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2'-deoxyadenosine 5'-triphosphate + L-arginine + tRNAArg = 2'-deoxyadenosine 5'-monophosphate + diphosphate + L-arginyl-tRNAArg
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2'-deoxyadenosine 5'-triphosphate + L-phenylalanine + tRNAPhe = 2'-deoxyadenosine 5'-monophosphate + diphosphate + L-phenylalanyl-tRNAPhe
show the reaction diagram
340,
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dATP + L-histidine + tRNAHis = dAMP + diphosphate + L-histidyl-tRNAHis
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2'-dATP + L-leucine + tRNALeu = 2'-dAMP + diphosphate + L-leucyl-tRNALeu
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dATP + lysine + tRNALys = dAMP + L-lysyl-tRNALys + diphosphate
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dATP + acetate + CoA = dAMP + diphosphate + acetyl-CoA
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dATP + a fatty acid + [acyl-carrier protein] = dAMP + diphosphate + fatty acid-[acyl-carrier protein]
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dATP + acetate + citrate (pro-3S)-lyase = dAMP + diphosphate + citrate(pro-3S)-lyase
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dATP + fatty acid + CoA = dAMP + diphosphate + acyl-CoA
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dATP + cholate + CoA = dAMP + diphosphate + choloyl-CoA
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dATP + deamido-NAD+ + NH3 = dAMP + diphosphate + NAD+
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dATP + L-citrulline + L-Asp = dAMP + diphosphate + L-argininosuccinate
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dATP + (ribonucleotide)n + (ribonucleotide)m = dAMP + phosphate + (ribonucleotide)n+m
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation, can replace AMP or ADP
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Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulation
-
activation, about 25% as efficient as AMP
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10.0 mM, relative activity 154%
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Inhibitor in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.2 mM, 36% inhibition
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competitive, dTMP as substrate
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10-15% inhibition at 5 mM
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5 mM, about 15% inhibition
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competitive inhibitor of partial type, dAMP forming a complex with Sma nuc does not completely prevent the RNA binding and reduces the enzyme affinity to RNA substrate in competition with RNA for the binding site
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decreased IMP cyclohydrolase activity by 10-50%
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16% inhibition at 17 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.0066
-
pH 7.5, 37°C, recombinant wild-type enzyme

KM Value (29 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.25
-
pH 7.5, 37°C, recombinant wild-type enzyme
1
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cosubstrate ATP
0.1
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pH 6.8, 25ºC

Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.9
-
-
0.028
-
pH 7.6, 37°C, recombinant deoxyguanosine kinase
0.15
-
dTMP as substrate, pH 7.6, 37°C
0.085
-
-
0.06
-
pH 8.5, 37°C
0.165
-
pH 7.6, 37°C

References & Links

Links to other databases for 2'-deoxyadenosine 5'-monophosphate

ChEBI
PubChem
ChEBI
PubChem