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Record Information
Version1.0
Creation Date2016-09-30 22:18:58 UTC
Update Date2019-02-05 19:56:55 UTC
MCDB ID BMDB00050
Secondary Accession NumbersNone
Metabolite Identification
Common NameAdenosine
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 drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Adenosine exists in all living species, ranging from bacteria to humans. Adenosine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolChEBI
6-Amino-9-beta-D-ribofuranosyl-9H-purineChEBI
9-beta-D-RibofuranosidoadenineChEBI
9-beta-D-Ribofuranosyl-9H-purin-6-amineChEBI
Ade-ribChEBI
Adenine deoxyribonucleosideChEBI
AdenocardChEBI
AdenocorChEBI
AdenoscanChEBI
AdenosinChEBI
AdenyldeoxyribosideChEBI
AdoChEBI
beta-D-AdenosineChEBI
DeoxyadenosineChEBI
DesoxyadenosineChEBI
6-Amino-9-b-D-ribofuranosyl-9H-purineGenerator
6-Amino-9-β-D-ribofuranosyl-9H-purineGenerator
9-b-D-RibofuranosidoadenineGenerator
9-Β-D-ribofuranosidoadenineGenerator
9-b-D-Ribofuranosyl-9H-purin-6-amineGenerator
9-Β-D-ribofuranosyl-9H-purin-6-amineGenerator
b-D-AdenosineGenerator
Β-D-adenosineGenerator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranoseHMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranoseHMDB
6-Amino-9beta-D-ribofuranosyl-9H-purineHMDB
6-Amino-9beta-delta-ribofuranosyl-9H-purineHMDB
9-beta-D-ArabinofuranosyladenineHMDB
9-beta-D-RibofuranosyladenineHMDB
9-beta-delta-ArabinofuranosyladenineHMDB
9-beta-delta-RibofuranosidoadenineHMDB
9-beta-delta-Ribofuranosyl-9H-purin-6-amineHMDB
9-beta-delta-RibofuranosyladenineHMDB
9beta-D-Ribofuranosyl-9H-purin-6-amineHMDB
9beta-D-RibofuranosyladenineHMDB
9beta-delta-Ribofuranosyl-9H-purin-6-amineHMDB
9beta-delta-RibofuranosyladenineHMDB
Adenine nucleosideHMDB
Adenine ribosideHMDB
Adenine-9beta-D-ribofuranosideHMDB
Adenine-9beta-delta-ribofuranosideHMDB
beta-AdenosineHMDB
beta-delta-AdenosineHMDB
BonitonHMDB
MyocolHMDB
NucleocardylHMDB
SandesinHMDB
Chemical FormulaC10H13N5O4
Average Molecular Weight267.2413
Monoisotopic Molecular Weight267.096753929
IUPAC Name(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Nameadenosine
CAS Registry Number58-61-7
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=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
InChI KeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
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
Experimental Properties
PropertyValueReference
Melting Point235.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility37 mg/mLHuman Metabolome Project
LogP-1.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m³·mol⁻¹ChemAxon
Polarizability25.28 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0f7w-1890000000-5c70a5423faa5e8eceafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-001v-0691000000-8f88854b7d5adec5c558JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001s-0790000000-cc3bcd977e11efd4ea25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gc0-0590000000-05874cecded3009c1f4dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fsv-1792000000-b37fd6826f28aaf9e825JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7w-1890000000-5c70a5423faa5e8eceafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001v-0691000000-8f88854b7d5adec5c558JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001s-0790000000-cc3bcd977e11efd4ea25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gc0-0590000000-05874cecded3009c1f4dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fsv-1792000000-b37fd6826f28aaf9e825JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4v-9560000000-986f3b1dfa5d898ed7a2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c4-6912500000-ae103f43432726c1ad22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-0890000000-588861a9494ab4680698JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-dd7cbed8e76c6e783831JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-c6644520b5943b59403dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0090000000-3d4fd8ea211eaed10531JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-cb58ec56a5faa09c9a02JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-9559aa07ec13a688fb16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-f7c1371d8e1058df3a32JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0940000000-da71247788bf1ba222e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0920000000-f2e8ec028abdd674b5e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0910000000-815ed65588c07415cd65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-1910000000-2780e737da8848411c4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-053r-1900000000-c6c1128990661334c15bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0090000000-106e7131507fadd4befbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-1c53823486cd2c23f90eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f0313435db4847490fd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-dcd4c2972882dcd7535aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-2900000000-5ee474864189cef6df64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-17edf36faf6eb5750912JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-0591143763a0bad31c23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0290000000-f1d71a97ce39145c8e31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kr-0950000000-9bbdbb14aed287ad5ac8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-35f90965f1f3c2b3236bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-f360cca994696d7ae735JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-42bee9785f9b55b32eeaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c8cda6a661ace060572cJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified1.4 uM details
HMDB IDHMDB0000050
DrugBank IDDB00640
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003554
KNApSAcK IDC00007444
Chemspider ID54923
KEGG Compound IDC00212
BioCyc IDADENOSINE
BiGG ID34273
Wikipedia LinkAdenosine
METLIN ID86
PubChem Compound60961
PDB IDNot Available
ChEBI ID16335
References
Synthesis ReferenceLiao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
  2. Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. [PubMed:11242448 ]
  3. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.