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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: adenine

Synonyms: 6-aminopurine

Superclasses: a nucleic acid component a nucleobase a purine base
an organic heterocyclic compound an organic heterobicyclic compound a purine
an organic heterocyclic compound an organic heterobicyclic compound a purine a purine base
an organic heterocyclic compound an organonitrogen heterocyclic compound a nucleobase a purine base
an organic heterocyclic compound an organonitrogen heterocyclic compound a purine
an organic heterocyclic compound an organonitrogen heterocyclic compound a purine a purine base

Chemical Formula: C5H5N5

Molecular Weight: 135.13 Daltons

Monoisotopic Molecular Weight: 135.0544951865 Daltons

SMILES: C1(N=C(C2(=C(N=1)N=CN2))N)

InChI: InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)

InChIKey: InChIKey=GFFGJBXGBJISGV-UHFFFAOYSA-N

Unification Links: CAS:73-24-5 , ChEBI:16708 , ChemSpider:185 , DrugBank:DB00173 , HMDB:HMDB00034 , IAF1260:34039 , KEGG:C00147 , MetaboLights:MTBLC16708 , PubChem:190

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 125.6056 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

adenine and adenosine salvage I , adenine and adenosine salvage II :
AMP + diphosphate ← adenine + 5-phospho-α-D-ribose 1-diphosphate

adenine and adenosine salvage IV :
AMP + diphosphate ← adenine + 5-phospho-α-D-ribose 1-diphosphate
adenine + H+ + H2O → ammonium + hypoxanthine

Not in pathways:
adenine + hydroxyl radical → isoguanine + H+

Reactions known to produce the compound:

1,4-dihydroxy-6-naphthoate biosynthesis II :
6-amino-6-deoxyfutalosine + H2O → dehypoxanthine futalosine + adenine

adenine and adenosine salvage II :
adenosine + H2O → D-ribofuranose + adenine

adenosine nucleotides degradation III :
AMP + H2O → D-ribofuranose 5-phosphate + adenine

adenosine nucleotides degradation IV :
AMP + phosphate → adenine + α-D-ribose 1,5-bisphosphate

autoinducer AI-2 biosynthesis I , autoinducer AI-2 biosynthesis II (Vibrio) , S-adenosyl-L-methionine cycle I :
S-adenosyl-L-homocysteine + H2O ← S-ribosyl-L-homocysteine + adenine

citrate lyase activation , malonate decarboxylase activation :
3'-dephospho-CoA + ATP + H+ → 2'-(5''-triphospho-α-D-ribosyl)-3'-dephospho-CoA + adenine

cytokinins degradation :
cis-zeatin + FAD + H2O + H+ → 3-methyl-4-cis-hydroxy-2-butenal + adenine + FADH2
N6-dimethylallyladenine + FAD + H2O + H+ → 3-methyl-2-butenal + adenine + FADH2
trans-zeatin + FAD + H2O + H+adenine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2

fluoroacetate and fluorothreonine biosynthesis :
5'-deoxy-5'-fluoroadenosine + phosphate → adenine + 5-fluoro-5-deoxy-D-ribose 1-phosphate

hopanoid biosynthesis (bacteria) :
adenosyl hopane + H2O → ribosyl hopane + adenine

methylphosphonate degradation I , methylphosphonate degradation II :
methylphosphonate + ATP → α-D-ribose-1-methylphosphonate-5-triphosphate + adenine

queuosine biosynthesis :
a 7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine → an epoxyqueuosine34 in tRNA + adenine + L-methionine + 2 H+

S-methyl-5'-thioadenosine degradation I , S-methyl-5'-thioadenosine degradation IV :
S-methyl-5'-thioadenosine + H2O → S-methyl-5-thio-D-ribose + adenine

S-methyl-5'-thioadenosine degradation II :
S-methyl-5'-thioadenosine + phosphate → adenine + S-methyl-5-thio-α-D-ribose 1-phosphate

salinosporamide A biosynthesis :
5'-deoxy-5'-chloroadenosine + phosphate → 5-chloro-5-deoxyribose 1-phosphate + adenine

Not in pathways:
5'-deoxyadenosine + H2O → 5-deoxy-D-ribose + adenine
1-ethyladenine + 2-oxoglutarate + oxygen → adenine + CO2 + acetaldehyde + succinate
N1-methyladenine + 2-oxoglutarate + oxygen → adenine + CO2 + formaldehyde + succinate

arsenate detoxification I (glutaredoxin) :
a purine ribonucleoside + arsenate → a purine base + ribose-1-arsenate


a purine ribonucleoside + H2O → D-ribofuranose + a purine base

Reactions known to both consume and produce the compound:

adenine and adenosine salvage I , adenine and adenosine salvage III , adenine and adenosine salvage V , purine ribonucleosides degradation :
adenosine + phosphate ↔ adenine + α-D-ribose-1-phosphate

purine deoxyribonucleosides degradation I :
2'-deoxyadenosine + phosphate ↔ adenine + 2-deoxy-α-D-ribose 1-phosphate

Not in pathways:
a purine ribonucleoside + phosphate ↔ a purine base + α-D-ribose-1-phosphate

In Reactions of unknown directionality:

Not in pathways:
N6-dimethylallyladenine + an oxidized electron acceptor + H2O = 3-methyl-2-butenal + adenine + a reduced electron acceptor
5'-deoxyadenosine + phosphate = 5-deoxy-α-ribose 1-phosphate + adenine
adenine4324 in 28S rRNA + H2O = a 28S rRNA containing an apurinic site + adenine


a purine 2'-deoxyribonucleoside + phosphate = a purine base + 2-deoxy-α-D-ribose 1-phosphate


a D-ribosyl-base(1) + a base(2) = a D-ribosyl-base(2) + a base(1)
a 2-deoxy-D-ribosyl-base(1) + a base(2) = a 2-deoxy-D-ribosyl-base(2) + a base(1)

In Transport reactions:
adenine[extracellular space] + H+[extracellular space]adenine[cytosol] + H+[cytosol] ,
adenine[periplasmic space] + H+[periplasmic space]adenine[cytosol] + H+[cytosol] ,
adenine[periplasmic space]adenine[cytosol]

Enzymes inhibited by adenine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: MTA nucleosidase [Guranowski83a] , adenosine nucleosidase [Guranowski77]

Inhibitor (Noncompetitive) of: 7,8-diaminopelargonic acid synthase [Stoner75]

Inhibitor (Mechanism unknown) of: 7,8-dihydropterin deaminase [Kim09e] , guanine deaminase [Kim09e] , D-galacturonate dehydrogenase [Wagner76] , MTR kinase [Guranowski83b]


References

Guranowski77: Guranowski A, Schneider Z (1977). "Purification and characterization of adenosine nucleosidase from barley leaves." Biochim Biophys Acta 482(1);145-58. PMID: 861230

Guranowski83a: Guranowski A.B., Chiang P.K., Cantoni G.L. "5'-Methylthioadenosine nucleosidase (Lupinus luteus seeds)." Methods in enzymology (1983) 94 : 365-369.

Guranowski83b: Guranowski A. "Plant 5-methylthioribose kinase." Plant Physiol. (1983) 71 : 932-935.

Kim09e: Kim J, Park SI, Ahn C, Kim H, Yim J (2009). "Guanine deaminase functions as dihydropterin deaminase in the biosynthesis of aurodrosopterin, a minor red eye pigment of Drosophila." J Biol Chem 284(35);23426-35. PMID: 19567870

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Stoner75: Stoner GL, Eisenberg MA (1975). "Biosynthesis of 7, 8-diaminopelargonic acid from 7-keto-8-aminopelargonic acid and S-adenosyl-L-methionine. The kinetics of the reaction." J Biol Chem 1975;250(11);4037-43. PMID: 1092682

Wagner76: Wagner G, Hollmann S (1976). "Uronic acid dehydrogenase from Pseudomonas syringae. Purification and properties." Eur J Biochem 61(2);589-96. PMID: 2471


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, biocyc14.