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Record Information
Version1.0
Creation Date2016-09-30 22:18:58 UTC
Update Date2020-05-21 16:28:53 UTC
BMDB IDBMDB0000050
Secondary Accession Numbers
  • BMDB00050
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Lysosome
  • Mitochondria
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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) (Non-derivatized)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-EI-TOF (Non-derivatized)splash10-0f7w-1890000000-5c70a5423faa5e8eceafView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001v-0691000000-8f88854b7d5adec5c558View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001s-0790000000-cc3bcd977e11efd4ea25View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gc0-0590000000-05874cecded3009c1f4dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fsv-1792000000-b37fd6826f28aaf9e825View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4v-9560000000-986f3b1dfa5d898ed7a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c4-6912500000-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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Lysosome
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Colostrum
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified1.4 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified150+/-114 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000050
DrugBank IDDB00640
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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.

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P55859
Molecular weight:
32037.0
Reactions
Adenosine + Hydrogen phosphate → Adenine + Ribose 1-phosphatedetails
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
AHCYL1
Uniprot ID:
A5PKK6
Molecular weight:
68585.0
General function:
Coenzyme transport and metabolism
Specific function:
May regulate the electrogenic sodium/bicarbonate cotransporter SLC4A4 activity and Mg(2+)-sensitivity. On the contrary of its homolog AHCYL1, does not regulate ITPR1 sensitivity to inositol 1,4,5-trisphosphate (By similarity).
Gene Name:
AHCYL2
Uniprot ID:
A6QLP2
Molecular weight:
66774.0
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine (By similarity). Plays an important role in purine metabolism and in adenosine homeostasis (By similarity). Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events (By similarity). Acts as a positive regulator of T-cell coactivation, by binding DPP4 (By similarity). Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion (By similarity). Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion (PubMed:23240012). Enhances CD4+ T-cell differentiation and proliferation (By similarity). Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change (By similarity). Stimulates plasminogen activation (By similarity). Plays a role in male fertility (By similarity). Plays a protective role in early postimplantation embryonic development (By similarity).
Gene Name:
ADA
Uniprot ID:
P56658
Molecular weight:
40919.0
Reactions
Adenosine + Water → Inosine + Ammoniadetails
General function:
Coenzyme transport and metabolism
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:
AHCY
Uniprot ID:
Q3MHL4
Molecular weight:
47638.0
Reactions
Se-Adenosylselenohomocysteine + Water → Selenohomocysteine + Adenosinedetails
S-Adenosylhomocysteine + Water → Homocysteine + Adenosinedetails
General function:
Not Available
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase.
Gene Name:
ADORA3
Uniprot ID:
Q0VC81
Molecular weight:
35911.0
General function:
Involved in adenosine receptor activity, G-protein coupled
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase (By similarity).
Gene Name:
ADORA2B
Uniprot ID:
Q1LZD0
Molecular weight:
36385.0
General function:
Involved in hydrolase activity
Specific function:
Component of the cleavage factor Im (CFIm) complex that functions as an activator of the pre-mRNA 3'-end cleavage and polyadenylation processing required for the maturation of pre-mRNA into functional mRNAs. CFIm contributes to the recruitment of multiprotein complexes on specific sequences on the pre-mRNA 3'-end, so called cleavage and polyadenylation signals (pA signals). Most pre-mRNAs contain multiple pA signals, resulting in alternative cleavage and polyadenylation (APA) producing mRNAs with variable 3'-end formation. The CFIm complex acts as a key regulator of cleavage and polyadenylation site choice during APA through its binding to 5'-UGUA-3' elements localized in the 3'-untranslated region (UTR) for a huge number of pre-mRNAs. NUDT21/CPSF5 activates indirectly the mRNA 3'-processing machinery by recruiting CPSF6 and/or CPSF7. Binds to 5'-UGUA-3' elements localized upstream of pA signals that act as enhancers of pre-mRNA 3'-end processing. The homodimer mediates simultaneous sequence-specific recognition of two 5'-UGUA-3' elements within the pre-mRNA. Plays a role in somatic cell fate transitions and pluripotency by regulating widespread changes in gene expression through an APA-dependent function. Binds to chromatin. Binds to, but does not hydrolyze mono- and di-adenosine nucleotides.
Gene Name:
NUDT21
Uniprot ID:
Q3ZCA2
Molecular weight:
26227.0
General function:
Involved in adenosine receptor activity, G-protein coupled
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
ADORA1
Uniprot ID:
P28190
Molecular weight:
36593.0