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BRENDA support

Ligand adenosine

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Basic Ligand Information

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

Related pathways

Pathway Source
Pathways
BRENDA
methionine metabolism, purine metabolism
KEGG
ABC transporters, Alcoholism, cAMP signaling pathway, cGMP-PKG signaling pathway, Morphine addiction more
MetaCyc
1-tuberculosinyladenosine biosynthesis, adenine and adenosine salvage I, adenine and adenosine salvage II, adenine and adenosine salvage III, adenine and adenosine salvage V more


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (37 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine + O2 = 9-riburonosyladenine + H2O2
show the reaction diagram
-
tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
show the reaction diagram
-
adenosine + H2O = 6-aminopurine + D-ribofuranose
show the reaction diagram
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adenosine + H2O = inosine + NH3
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (25 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N6-(DELTA2-isopentenyl)adenosine + FAD + H2O = adenosine + 3-methylbut-2-enal + FADH2
show the reaction diagram
-
-
S-adenosyl-L-methionine + H2O = adenosine + L-methionine + H+
show the reaction diagram
-
-
AMP + thymidine = adenosine + dTMP
show the reaction diagram
-
-
3'-AMP + H2O = adenosine + phosphate
show the reaction diagram
-
S-adenosyl-L-homocysteine + H2O = adenosine + L-homocysteine
show the reaction diagram
-
-
5'-AMP + H2O = adenosine + phosphate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (199 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine + O2 = 9-riburonosyladenine + H2O
show the reaction diagram
-
adenosine + O2 = 9-riburonosyladenine + H2O2
show the reaction diagram
-
tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
show the reaction diagram
-
AMP + adenosine = adenosine + AMP
show the reaction diagram
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ATP + adenosine = ADP + adenosine 5'-phosphate
show the reaction diagram
-
3 adenosine = ?
show the reaction diagram
-
adenosine + H2O = adenine + D-ribose
show the reaction diagram
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adenosine + H2O = adenine + D-ribose
show the reaction diagram
-
adenosine + H2O = ?
show the reaction diagram
-
adenosine + H2O = D-ribose + adenine
show the reaction diagram
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adenosine + H2O = adenine + D-ribose
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
adenosine + H2O = inosine + NH3
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
-
adenosine + H2O = ?
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
-
adenosine + H2O = inosine + NH3
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (198 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2 [Fe(II)-cytochrome b5] + 2 H+ + N6-hydroxyadenosine = 2 [Fe(III)-cytochrome b5] + H2O + adenosine
show the reaction diagram
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-
adenosine N-oxide + electron donor = adenosine + H2O + oxidized electron donor
show the reaction diagram
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AMP + trans-farnesyl diphosphate = adenosine + trans-farnesyl triphosphate
show the reaction diagram
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-
(A)40 + 38 H2O = adenosine + 39 AMP
show the reaction diagram
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-
3'AMP + H2O = adenosine + phosphate
show the reaction diagram
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AMP + H2O = adenosine + phosphate
show the reaction diagram
134580, -
-
AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
2'-AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
NAD+ + H2O = adenosine + nicotinamide + ?
show the reaction diagram
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S-adenosyl-L-homocysteine + H2O = adenosine + L-homocysteine
show the reaction diagram
289034, -
-
3'-AMP + H2O = adenosine + phosphate
show the reaction diagram
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-
cAMP + H2O = adenosine + phosphate
show the reaction diagram
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AMP + H2O = adenosine + phosphate
show the reaction diagram
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AMP + H2O = adenosine + phosphate
show the reaction diagram
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ApA + H2O = 3'-AMP + adenosine
show the reaction diagram
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GpA + H2O = guanosine 3'-phosphate + adenosine
show the reaction diagram
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AMP + H2O = adenosine + phosphate
show the reaction diagram
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-

Enzyme Cofactor/Cosubstrate (2 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (26 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
very weak activation
-
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 dephosphorylated 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 (286 results)

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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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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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slight inhibition
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competitive with MgATP2-
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competitive
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concentrations above 0.1 mM lead to reduction in enzyme activity
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substrate: 3'-AMP or bis-4-nitrophenylphosphate
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addition of 1.4 mM, inhibition 54.7%
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competitive
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78% inhibition at 0.5 mM
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inhibits deamination of ATP
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slight inhibition
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decrease in activity may be due to downregulation of enzyme expression
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competitive inhibition, Ki: 2.7 mM
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weak inhibitor
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uncompetitive versus L-adenosyl-L-methionine
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weak inhibition
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-
-
-
-
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87.3% residual activity at 5 mM
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inhibits independently of the A3 receptor
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3D Structure of Enzyme-Ligand-Complex (PDB) (234 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (120 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.0549
-
pH 7.4, 25°C
0.084
-
pH 8.0, 22°C
3.8
-
-
0.3
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at pH 7.4 and 25°C
0.3
-
pH 7.4, 25°C
0.06
-
-

KM Value (265 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.048
-
-
0.023
-
pH 7.4, 25°C
0.04
-
reaction with deoxyinosine
1
-
pH 6.7, 85°C
1.28
-
38°C, pH 7.5
0.0061
-
pH 7.5, 37°C, reaction with 4-nitrophenyl phosphate
0.0075
-
at pH 7.4 and 25°C
0.0075
-
pH 7.4, 25°C

Ki Value (45 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
36
-
pH 7.8, 25°C, substrate: NAD+
0.42
-
at pH 7.0
4.8
-
inhibition of the recombinant FAD domain
0.21
-
pH 8.6
580
-
-
0.8
-
-
0.32
-
pH 6.8, 25ºC
2.7
-
competitive inhibition
0.5
-
-

IC50 Value (11 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.082
-
pH 7.0
0.0042
-
37°C, pH 7.2
0.021
-
pH 4.8
0.01846
-
pH and temperature not specified in the publication
0.095
-
in 10 mM Tris-HCl pH 7.5, at 30°C

References & Links

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Links to other databases for adenosine

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EXTERNAL LINKS
ChEBI
PubChem
UniChem