Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000016
Name: Adenosine
Description:Adenosine is nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter.
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-D-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-delta-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-b-δ-ribofuranose
  • 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-D-ribofuranose
  • 1-(6-amino-9H-Purin-9-yl)-1-deoxy-β-δ-ribofuranose
  • 6-amino-9b-D-Ribofuranosyl-9H-purine
  • 6-amino-9b-delta-Ribofuranosyl-9H-purine
  • 6-amino-9b-δ-Ribofuranosyl-9H-purine
  • 6-Amino-9beta-D-ribofuranosyl-9H-purine
  • 6-Amino-9beta-delta-ribofuranosyl-9H-purine
  • 6-amino-9β-D-Ribofuranosyl-9H-purine
  • 6-amino-9β-δ-Ribofuranosyl-9H-purine
  • 9-b-D-Arabinofuranosyladenine
  • 9-b-D-Ribofuranosidoadenine
  • 9-b-D-Ribofuranosyl-9H-purin-6-amine
  • 9-b-D-Ribofuranosyladenine
  • 9-b-delta-Arabinofuranosyladenine
  • 9-b-delta-Ribofuranosidoadenine
  • 9-b-delta-Ribofuranosyl-9H-purin-6-amine
  • 9-b-delta-Ribofuranosyladenine
  • 9-b-δ-Arabinofuranosyladenine
  • 9-b-δ-Ribofuranosidoadenine
  • 9-b-δ-Ribofuranosyl-9H-purin-6-amine
  • 9-b-δ-Ribofuranosyladenine
  • 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
  • 9-β-D-Arabinofuranosyladenine
  • 9-β-D-Ribofuranosidoadenine
  • 9-β-D-Ribofuranosyl-9H-purin-6-amine
  • 9-β-D-Ribofuranosyladenine
  • 9-β-δ-Arabinofuranosyladenine
  • 9-β-δ-Ribofuranosidoadenine
  • 9-β-δ-Ribofuranosyl-9H-purin-6-amine
  • 9-β-δ-Ribofuranosyladenine
  • 9b-D-Ribofuranosyl-9H-purin-6-amine
  • 9b-D-Ribofuranosyladenine
  • 9b-delta-Ribofuranosyl-9H-purin-6-amine
  • 9b-delta-Ribofuranosyladenine
  • 9b-δ-Ribofuranosyl-9H-purin-6-amine
  • 9b-δ-Ribofuranosyladenine
  • 9beta-D-ribofuranosyl-9H-Purin-6-amine
  • 9beta-D-Ribofuranosyladenine
  • 9beta-delta-ribofuranosyl-9H-Purin-6-amine
  • 9beta-delta-Ribofuranosyladenine
  • 9β-D-Ribofuranosyl-9H-purin-6-amine
  • 9β-D-Ribofuranosyladenine
  • 9β-δ-Ribofuranosyl-9H-purin-6-amine
  • 9β-δ-Ribofuranosyladenine
  • Adenine nucleoside
  • Adenine riboside
  • Adenine-9b-D-ribofuranoside
  • Adenine-9b-delta-ribofuranoside
  • Adenine-9b-δ-ribofuranoside
  • Adenine-9beta-D-Ribofuranoside
  • Adenine-9beta-delta-Ribofuranoside
  • Adenine-9β-D-ribofuranoside
  • Adenine-9β-δ-ribofuranoside
  • Adenine-D-ribose
  • Adenocard
  • Adenocor
  • Adenoscan
  • Adenosin
  • b-Adenosine
  • B-D-Adenosine
  • b-delta-Adenosine
  • b-δ-Adenosine
  • Beta-Adenosine
  • Beta-D-Adenosine
  • Beta-delta-Adenosine
  • Boniton
  • Myocol
  • Nucleocardyl
  • Sandesin
  • β-Adenosine
  • β-D-Adenosine
  • β-δ-Adenosine
Chemical Formula: C10H13N5O4
Average Molecular Weight: 267.2413
Monoisotopic Molecular Weight: 267.096753929
CAS number: 58-61-7
IUPAC Name:(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name: adenosine
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleosides
Sub ClassNot Available
Direct Parent Purine nucleosides
Alternative Parents
  • Purine ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 235.5 °C
Experimental Properties:
Predicted Properties
Water Solubility14.0 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
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
GC-MSGC-MS Spectrum - GC-MSNot Available
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
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
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  • Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. Pubmed: 6656991
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Synthesis Reference: Liao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID60961
Kegg IDC00212
ChemSpider ID54923
Ligand ExpoADN


General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
Locus Tag:
Molecular weight:
50.4 kDa
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of Pseudomonas aeruginosa in stationary growth phase
Gene Name:
Locus Tag:
Molecular weight:
26.4 kDa
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
Locus Tag:
Molecular weight:
38 kDa
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in riboflavin synthase activity
Specific function:
Riboflavin synthase is a bifunctional enzyme complex catalyzing the formation of riboflavin from 5-amino-6-(1'-D)- ribityl-amino-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydrohy-2- butanone-4-phosphate via 6,7-dimethyl-8-lumazine. The alpha subunit catalyzes the dismutation of 6,7-dimethyl-8-lumazine to riboflavin and 5-amino-6-(1'-D)-ribityl-amino-2,4(1H,3H)- pyrimidinedione
Gene Name:
Locus Tag:
Molecular weight:
16.4 kDa
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
Gene Name:
Locus Tag:
Molecular weight:
23.1 kDa
ATP + AMP = 2 ADP.
General function:
Energy production and conversion
Specific function:
Deaminates adenosine-34 to inosine in tRNA-Arg2. Mutation in this protein makes Pseudomonas aeruginosa resistant to the toxic proteins encoded by the gef gene family. Essential for cell viability
Gene Name:
Locus Tag:
Molecular weight:
46.8 kDa
Adenosine + H(2)O = inosine + NH(3).