Ligand adenosine

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Basic Ligand Information

Molecular Structure
Picture of adenosine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H13N5O4
adenosine
OIRDTQYFTABQOQ-KQYNXXCUSA-N
Synonyms:
3-beta-ribofuranosyladenine


Show all pahtways known for Show all BRENDA pathways known for adenosine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (78 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine + O2 = 9-riburonosyladenine + H2O2
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tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
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adenosine + H2O = 6-aminopurine + D-ribofuranose
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adenosine + H2O = inosine + NH3
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In Vivo Product in Enzyme-catalyzed Reactions (65 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N6-(DELTA2-isopentenyl)adenosine + FAD + H2O = adenosine + 3-methylbut-2-enal + FADH2
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S-adenosyl-L-methionine + H2O = adenosine + L-methionine + H+
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AMP + thymidine = adenosine + dTMP
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3'-AMP + H2O = adenosine + phosphate
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5'-AMP + H2O = adenosine + phosphate
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Substrate in Enzyme-catalyzed Reactions (297 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine + O2 = 9-riburonosyladenine + H2O
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adenosine + O2 = 9-riburonosyladenine + H2O2
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2'-deoxycytidine + adenosine = 2'-deoxyadenosine + cytosine
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tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
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ATP + adenosine = ADP + ?
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AMP + adenosine = adenosine + AMP
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ATP + adenosine = ADP + adenosine 5'-phosphate
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3 adenosine = ?
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adenosine + H2O = adenine + D-ribose
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adenosine + H2O = adenine + D-ribose
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adenosine + H2O = ?
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adenosine + H2O = D-ribose + adenine
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adenosine + H2O = adenine + D-ribose
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adenosine + H2O = inosine + NH3
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adenosine + H2O = inosine + NH3
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adenosine + H2O = inosine + NH3
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adenosine + H2O = inosine + NH3
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adenosine + H2O = inosine + NH3
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adenosine + H2O = ?
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adenosine + H2O = inosine + NH3
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adenosine + H2O = inosine + NH3
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Product in Enzyme-catalyzed Reactions (280 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine N-oxide + electron donor = adenosine + H2O + oxidized electron donor
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AMP + trans-farnesyl diphosphate = adenosine + trans-farnesyl triphosphate
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(A)40 + 38 H2O = adenosine + 39 AMP
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3'AMP + H2O = adenosine + phosphate
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AMP + H2O = adenosine + phosphate
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AMP + H2O = adenosine + phosphate
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AMP + H2O = adenosine + phosphate
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2'-AMP + H2O = adenosine + phosphate
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NAD+ + H2O = adenosine + nicotinamide
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3'-AMP + H2O = adenosine + phosphate
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cAMP + H2O = adenosine + phosphate
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AMP + H2O = adenosine + phosphate
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AMP + H2O = adenosine + phosphate
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ApA + H2O = 3'-AMP + adenosine
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AMP + H2O = adenosine + phosphate
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Enzyme Cofactor/Cosubstrate (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (68 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
very weak activation
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adenosine activates PI3K and induces Akt phosphorylation leading to induction of hemeoxygenase-1, HO-1, expression in microglia. Adenosine acts as an endogenous regulator of brain inflammation via modulation of microglial reactive oxygen species production, mechanism, overview
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slight activation
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adenosine-induced vasodilation in cerebral microvessesls involves cGMP and cGMP-dependent protein kinase
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activation by nucleotides, most efficient in presence of two different nucleotides
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less effective than ATP
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2',3'-cyclic nucleotide phosphodiesterase activity
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potentiates mast cell tPA activity and tPA gene expression, abolished in the presence of adenosine deaminase
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extracellular adenosine induces apoptosis by activating caspase-9 and caspase-3 in association with mitochondrial damage via A2a adenosine receptors, induction dose-dependent (1-20 mM) and time-dependent (24-72 h)
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activates
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approx. 10fold activation of dephosporylated ODC at 1 mM, approx. 2fold activation of native ODC
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activation to 120-130%, allosteric
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Inhibitor in Enzyme-catalyzed Reactions (341 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
48% inhibition of fructose 6-phosphate reduction
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competitive vs. NAD+
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inhibition probably due to inhibition of glutathione reductase in coupled assay
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inhibition of the recombinant FAD domain
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plus homocysteine
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0.7 mM, 30% inhibition
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weak inhibition
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weak inhibition
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at 10 mM, recombinant HXK1: 36% inhibition, recombinant HXK2: 5% inhibition
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0.5 mM, 5% inhibition of DGK I and 28% inhibition of DGK IV
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above 0.1 mM
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