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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 Solubility14.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m3·mol-1ChemAxon
Polarizability25.27 Å3ChemAxon
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 Pw002384Pw002384 greyscalePw002384 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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0f7w-1890000000-5c70a5423faa5e8eceafView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-001v-0691000000-8f88854b7d5adec5c558View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001s-0790000000-cc3bcd977e11efd4ea25View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gc0-0590000000-05874cecded3009c1f4dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fsv-1792000000-b37fd6826f28aaf9e825View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a4v-9560000000-986f3b1dfa5d898ed7a2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f7w-1890000000-5c70a5423faa5e8eceafView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-001v-0691000000-8f88854b7d5adec5c558View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-001s-0790000000-cc3bcd977e11efd4ea25View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9460000000-3ae19bfaa5d2df72f9b1View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0gc0-0590000000-05874cecded3009c1f4dView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0fsv-1792000000-b37fd6826f28aaf9e825View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-01c4-6912500000-ae103f43432726c1ad22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-0890000000-588861a9494ab4680698View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-dd7cbed8e76c6e783831View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-c6644520b5943b59403dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0090000000-3d4fd8ea211eaed10531View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-cb58ec56a5faa09c9a02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-9559aa07ec13a688fb16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-f7c1371d8e1058df3a32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0940000000-da71247788bf1ba222e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0920000000-f2e8ec028abdd674b5e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0910000000-815ed65588c07415cd65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-1910000000-2780e737da8848411c4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-053r-1900000000-c6c1128990661334c15bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0090000000-106e7131507fadd4befbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-1c53823486cd2c23f90eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f0313435db4847490fd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-dcd4c2972882dcd7535aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-2900000000-5ee474864189cef6df64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-17edf36faf6eb5750912View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-0591143763a0bad31c23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0290000000-f1d71a97ce39145c8e31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kr-0950000000-9bbdbb14aed287ad5ac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-35f90965f1f3c2b3236bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-f360cca994696d7ae735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-42bee9785f9b55b32eeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c8cda6a661ace060572cView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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:0xa4c80ab0>
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:0xa3b6d908>
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:0xa5edea54>
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:0xa3a43af0>
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:0xa4b4e28c>

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:0xa459e8c8>