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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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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 [Guranowski83] , adenosine nucleosidase [Guranowski77a]

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

Inhibitor (Mechanism unknown) of: 7,8-dihydropterin deaminase [Kim09d] , guanine deaminase [Kim09d] , D-galacturonate dehydrogenase [Wagner76] , MTR kinase [Guranowski83a]


References

Guranowski77a: Guranowski A, Schneider Z (1977). "Purification and characterization of adenosine nucleosidase from barley leaves." Biochim Biophys Acta 482(1);145-58. PMID: 861230

Guranowski83: Guranowski A.B., Chiang P.K., Cantoni G.L. "5'-Methylthioadenosine nucleosidase (Lupinus luteus seeds)." Methods in enzymology (1983) 94 : 365-369.

Guranowski83a: Guranowski A. "Plant 5-methylthioribose kinase." Plant Physiol. (1983) 71 : 932-935.

Kim09d: 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


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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 Sat Dec 20, 2014, biocyc14.