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Identification
YMDB IDYMDB00058
NameAdenosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenosine is a purine nucleoside. It is formed by a molecule of adenine attached to a ribose sugar molecule. Adenosine is the RNA nucleoside A. Adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP), as well as in signal transduction as cyclic adenosine monophosphate (cAMP).
Structure
Thumb
Synonyms
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose
  • 6-Amino-9beta-D-ribofuranosyl-9H-purine
  • 6-Amino-9beta-delta-ribofuranosyl-9H-purine
  • 9-beta-D-Arabinofuranosyladenine
  • 9-beta-D-Ribofuranosidoadenine
  • 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  • 9-beta-d-Ribofuranosyladenine
  • 9-beta-delta-Arabinofuranosyladenine
  • 9-beta-delta-Ribofuranosidoadenine
  • 9-beta-delta-Ribofuranosyl-9H-purin-6-amine
  • 9-beta-delta-Ribofuranosyladenine
  • 9beta-D-ribofuranosyl-9H-Purin-6-amine
  • 9beta-D-Ribofuranosyladenine
  • 9beta-delta-ribofuranosyl-9H-Purin-6-amine
  • 9beta-delta-Ribofuranosyladenine
  • Adenine nucleoside
  • Adenine riboside
  • adenine-9beta-D-Ribofuranoside
  • adenine-9beta-delta-Ribofuranoside
  • Adenocard
  • Adenocor
  • Adenoscan
  • Adenosin
  • b-D-Adenosine
  • beta-Adenosine
  • beta-D-Adenosine
  • beta-delta-Adenosine
  • Boniton
  • Myocol
  • Nucleocardyl
  • Sandesin
  • (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • 6-amino-9-beta-D-Ribofuranosyl-9H-purine
  • Ade-rib
  • Adenine deoxyribonucleoside
  • Adenyldeoxyriboside
  • Ado
  • Deoxyadenosine
  • Desoxyadenosine
  • 6-amino-9-b-D-Ribofuranosyl-9H-purine
  • 6-amino-9-β-D-ribofuranosyl-9H-purine
  • 9-b-D-Ribofuranosidoadenine
  • 9-β-D-ribofuranosidoadenine
  • 9-b-D-Ribofuranosyl-9H-purin-6-amine
  • 9-β-D-ribofuranosyl-9H-purin-6-amine
  • β-D-adenosine
CAS number58-61-7
WeightAverage: 267.2413
Monoisotopic: 267.096753929
InChI KeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
InChIInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
IUPAC Name(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Nameadenosine
Chemical FormulaC10H13N5O4
SMILES[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point235.5 °C
Experimental Properties
PropertyValueReference
Water Solubility7 mg/mL [Adenocard product monograph]; 37 mg/mL [HMP experimental]PhysProp
LogP-1.05 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m³·mol⁻¹ChemAxon
Polarizability25.27 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
S-Adenosylhomocysteine + waterAdenosine + Homocysteine
KEGG Reactions
Adenosine monophosphate + waterAdenosine + phosphate
Adenosine + water + hydronAmmonium + Inosine
Adenosine + waterD-Ribose + Adenine
Adenosine + Adenosine triphosphateAdenosine monophosphate + hydron + ADP
S-Adenosylhomocysteine + waterAdenosine + L-Homocysteine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
307 ± 15 µM hops, malted barleyanaerobicBaker's yeastPMID: 16448171
Conversion Details Here
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
  • Lecoq, K., Belloc, I., Desgranges, C., Daignan-Fornier, B. (2001). "Role of adenosine kinase in Saccharomyces cerevisiae: identification of the ADO1 gene and study of the mutant phenotypes." Yeast 18:335-342.11223943
  • Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
  • Tehlivets, O., Hasslacher, M., Kohlwein, S. D. (2004). "S-adenosyl-L-homocysteine hydrolase in yeast: key enzyme of methylation metabolism and coordinated regulation with phospholipid synthesis." FEBS Lett 577:501-506.15556636
  • Vickers, M. F., Yao, S. Y., Baldwin, S. A., Young, J. D., Cass, C. E. (2000). "Nucleoside transporter proteins of Saccharomyces cerevisiae. Demonstration of a transporter (FUI1) with high uridine selectivity in plasma membranes and a transporter (FUN26) with broad nucleoside selectivity in intracellular membranes." J Biol Chem 275:25931-25938.10827169
Synthesis Reference:Liao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634.
External Links:
ResourceLink
CHEBI ID16335
HMDB IDHMDB00050
Pubchem Compound ID60961
Kegg IDC00212
ChemSpider ID54923
FOODB IDFDB003554
WikipediaAdenosine
BioCyc IDADENOSINE

Enzymes

General function:
Involved in adenosine kinase activity
Specific function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. ADO1 does not play a major role in adenine utilization in yeast. Its physiological role could primarily be to recycle adenosine produced by the methyl cycle
Gene Name:
ADO1
Uniprot ID:
P47143
Molecular weight:
36372.0
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xb2582b60>
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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xb116bd5c>
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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xb1168760>
General function:
Involved in adenosylhomocysteinase activity
Specific function:
Adenosylhomocysteine is a competitive inhibitor of S- adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine
Gene Name:
SAH1
Uniprot ID:
P39954
Molecular weight:
49125.10156
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xabca93dc>
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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xb053a240>

Transporters

General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Has broad nucleoside selectivity (uridine, ademosine and cytidine) and most likely functions to transport nucleosides across intracellular membranes
Gene Name:
FUN26
Uniprot ID:
P31381
Molecular weight:
58316.69922
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0xb14ab0e4>