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Identification
YMDB IDYMDB00058
NameAdenosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenosine, also known as adenocard or ade-rib, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Adenosine is a strong basic compound (based on its pKa). Adenosine exists in all living species, ranging from bacteria to humans. Adenosine is a potentially toxic compound.
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
Description belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides 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 + phosphateRibose 1-phosphate + Adenine
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
ATP + adenosine → ADP + AMP.
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 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 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
S-adenosyl-L-homocysteine + H(2)O → L-homocysteine + adenosine.
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 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