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BRENDA support

Ligand adenine

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Basic Ligand Information

Molecular Structure
Picture of adenine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C5H5N5
adenine
GFFGJBXGBJISGV-UHFFFAOYSA-N
 Download
Synonyms:
6-amino-6-deoxyadenosine, 6-aminopurine, 9H-purine-6-amine

Related pathways

Pathway Source
Pathways
BRENDA
1,4-dihydroxy-6-naphthoate biosynthesis, methionine metabolism, purine metabolism
KEGG
Biosynthesis of secondary metabolites, Nucleotide metabolism, Purine metabolism, Zeatin biosynthesis
MetaCyc
(aminomethyl)phosphonate degradation, 1,4-dihydroxy-6-naphthoate biosynthesis II, 5'-deoxyadenosine degradation I, 5'-deoxyadenosine degradation II, adenine and adenosine salvage I more


Show all pahtways known for Show all BRENDA pathways known for adenine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (27 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2'-deoxy-D-ribosyl-uracil + adenine = 2'-deoxy-D-ribosyl-adenine + uracil
show the reaction diagram
thiamine + adenine = ?
show the reaction diagram
-
adenine + H2O = allopurinol + NH3
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (265 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + 3'-dephospho-CoA = 2'-(5''-triphosphoribosyl)-3'-dephospho-CoA + adenine
show the reaction diagram
-
-
AMP + phosphate = adenine + alpha-D-ribose 1,5-bisphosphate
show the reaction diagram
-
-
S-adenosyl-L-methionine + 7-aminomethyl-7-deazaguanine in tRNA(Tyr) = L-methionine + adenine + epoxyqueuosine in tRNA(Tyr)
show the reaction diagram
-
-
AMP + H2O = D-ribose 5-phosphate + adenine
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (91 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-phospho-alpha-D-ribose 1-diphosphate + adenine = AMP + diphosphate
show the reaction diagram
-
thiamine + adenine = ?
show the reaction diagram
-
O-acetyl-L-serine + adenine = 2-amino-3-(6-aminopurin-9-yl)-propanoate + acetate
show the reaction diagram
-
adenine + H2O = allopurinol + NH3
show the reaction diagram
-
adenine + H2O = allopurinol + NH3
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (1445 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N6-methyladenine + 2-oxoglutarate + O2 = adenine + formaldehyde + succinate + CO2
show the reaction diagram
-
-
2'-methyladenosine 5'-diphosphate + reduced dithiothreitol = adenine + 2'-deoxy-2'-methyladenosine + H2O
show the reaction diagram
-
adenosine-1N-oxide + reduced dichlorophenolindophenol = adenine + H2O + oxidized dichlorophenolindophenol
show the reaction diagram
-
-
AMP + phosphate = adenine + alpha-D-ribose 1,5-bisphosphate
show the reaction diagram
-
-
adenosine + H2O = D-ribose + adenine
show the reaction diagram
-
-
AMP + H2O = adenine + phosphate
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (10 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increases enzyme production
-
5 mM, activity of both isoenzymes is modestly enhanced
-
less effective than ATP
-
1 mM, activity: 194%, isoenzyme 2
-
activates
-

Inhibitor in Enzyme-catalyzed Reactions (207 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM, 70% inhibition after preincubation for 5 min
-
slight product inhibition
-
inhibition of the recombinant FAD domain
-
Kd: 180 microM
0.25 mM, 8% inhibition
-
competitive to ATP and 5-phospho-alpha-D-ribose 1-diphosphate
-
0.05 mM, 14% inhibition of exchange between free guanine with guanine
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noncompetitive inhibition against S-adenosyl-L-methionine and 7-(aminomethyl)-7-deazaguanine-tRNATyr
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weak inhibition
-
8 mM
-
1 mM, 25% inhibition
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weak
-
at 2.5 mM, strong
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poor inhibitor
1 mM: about 30% inhibition
-
competitive inhibition of deamination of adenosine 3'-phenylphosphonate
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0.2 mM, 27% inhibition
-
0.25 mM
-
slight inhibition
-
50% inhibition at 0.2 mM
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weak inhibition
-
-
-

3D Structure of Enzyme-Ligand-Complex (PDB) (516 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (55 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

KM Value (104 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0071
-
cosubstrate: NAD+
0.01
-
-
0.0029
-
-
0.023
-
-
0.023
-
pH 7.4, 25°C
0.0346
-
mutant K134S
9.5
-
-
26
-
-
0.032
-
-

Ki Value (12 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
26
-
inhibition of the recombinant FAD domain
580
-
80°C, pH 5.0
6.6
-
-
0.172
-
-
0.011
-
pH 7.5, 60°C
0.14
-
-
0.0087
-
pH 7.5, 30°C
0.3
-
in 50 mM potassium phosphate (pH 7.0), at 37°C
0.17
-
pH 7.5, 25°C
2.2
-
25°C, pH 7.8

IC50 Value (7 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0109
-
pH 7.5, 25°C
0.216
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.216
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C

References & Links

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Links to other databases for adenine

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EXTERNAL LINKS
ChEBI
PubChem
UniChem