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Identification
YMDB IDYMDB00887
NameAdenine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenine, also known as 6-aminopurine or Ade, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Adenine is a very strong basic compound (based on its pKa). Adenine exists in all living species, ranging from bacteria to humans. Adenine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1,6-Dihydro-6-iminopurine
  • 1H-Purin-6-amine
  • 1H-Purine-6-amine
  • 3,6-Dihydro-6-iminopurine
  • 6-Amino-1H-purine
  • 6-Amino-3H-purine
  • 6-Amino-7H-purine
  • 6-Amino-9H-purine
  • 6-amino-Purine
  • 6-Aminopurine
  • 9H-Purin-6-amine
  • 9H-Purin-6-yl-amin
  • 9H-purin-6-ylamine
  • 9H-Purine-6-amine
  • Ade
  • Adenine
  • Adeninimine
  • Vitamin B4
  • A
  • Adenin
  • Leucon
  • Vitamin b 4
  • 4, Vitamin b
  • b 4, Vitamin
CAS number73-24-5
WeightAverage: 135.1267
Monoisotopic: 135.054495185
InChI KeyGFFGJBXGBJISGV-UHFFFAOYSA-N
InChIInChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
IUPAC Name7H-purin-6-amine
Traditional IUPAC Namevitamin B4
Chemical FormulaC5H5N5
SMILES[H]N([H])C1=NC([H])=NC2=C1N([H])C([H])=N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point360 °C
Experimental Properties
PropertyValueReference
Water Solubility1.03 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-0.09 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)5.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB012266
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
Purine metabolismec00230 Map00230
SMPDB Reactions
phosphate + 5'-S-methyl-5'-thioadenosine5-Methylthioribose 1-phosphate + Adenine
Adenosine triphosphate + hydron + Dephospho-CoAAdenine + 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA
KEGG Reactions
phosphate + 5'-MethylthioadenosineS-Methyl-5-thio-alpha-D-ribose 1-phosphate + Adenine
water + hydron + AdenineHypoxanthine + Ammonium
Phosphoribosyl pyrophosphate + AdenineAdenosine monophosphate + Pyrophosphate
Adenosine + waterD-Ribose + Adenine
Adenosine + phosphateRibose 1-phosphate + Adenine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • ROUSH, A. H., SAEED, M. (1960). "Adenine metabolism in Saccharomyces cerevisiae adenase from bakers' yeast." Biochem Biophys Res Commun 2:43-47.14439573
  • Aranda, A., Jimenez-Marti, E., Orozco, H., Matallana, E., Del Olmo, M. (2006). "Sulfur and adenine metabolisms are linked, and both modulate sulfite resistance in wine yeast." J Agric Food Chem 54:5839-5846.16881685
  • Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). "Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites." J Biol Chem 278:49868-49873.14506228
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Baddiley, J.; Lythgoe, B.; Todd, A. R. Synthesis of purine nucleosides. II. A new and convenient synthesis of adenine. Journal of the Chemical Society (1943), 386-7.
External Links:
ResourceLink
CHEBI ID16708
HMDB IDHMDB00034
Pubchem Compound ID190
Kegg IDC00147
ChemSpider ID185
FOODB IDFDB012266
WikipediaAdenine
BioCyc IDADENINE

Enzymes

General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
PNP1
Uniprot ID:
Q05788
Molecular weight:
33754.60156
Reactions
Purine nucleoside + phosphate → purine + alpha-D-ribose 1-phosphate.
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Thiamine-regulated, high affinity import carrier of pyridoxine, pyridoxal and pyridoxamine
Gene Name:
TPN1
Uniprot ID:
P53099
Molecular weight:
64545.80078
General function:
Involved in deaminase activity
Specific function:
Adenosine + H(2)O = inosine + NH(3)
Gene Name:
AAH1
Uniprot ID:
P53909
Molecular weight:
39634.69922
Reactions
Adenosine + H(2)O → inosine + NH(3).
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
Gene Name:
APT1
Uniprot ID:
P49435
Molecular weight:
20586.59961
Reactions
AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis. May lack catalytic activity
Gene Name:
APT2
Uniprot ID:
P36973
Molecular weight:
19999.80078
Reactions
AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
Seems to be implicated in the regulation of the expression of the ADH2 gene
Gene Name:
MEU1
Uniprot ID:
Q07938
Molecular weight:
37856.30078
Reactions
S-methyl-5'-thioadenosine + phosphate → adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate
General function:
Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:
Also acts on cytidine
Gene Name:
URH1
Uniprot ID:
Q04179
Molecular weight:
37960.0
Reactions
Uridine + H(2)O → D-ribose + uracil.

Transporters

General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Probable purine-cytosine permease
Gene Name:
FCY21
Uniprot ID:
P40039
Molecular weight:
58049.60156
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
This permease has a broad specificity towards purines, and also transport cytosine and 5-methylcytosine but neither uracil nor thymine
Gene Name:
FCY2
Uniprot ID:
P17064
Molecular weight:
58200.69922
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Probable purine-cytosine permease
Gene Name:
FCY22
Uniprot ID:
Q12119
Molecular weight:
57326.69922