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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:32 UTC
NP-MRD IDNP0000860
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdenosine
DescriptionAdenosine is a 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. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
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 Mass267.2413 Da
Monoisotopic Mass267.09675 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Acanthopanax giraldiiKNApSAcK Database
Acanthus ebracteatusKNApSAcK Database
Acanthus ilicifoliusKNApSAcK Database
Adiantum lunulatumKNApSAcK Database
Allium tuberosum Rottl.ex Spreng.KNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Asparagus officinalisKNApSAcK Database
Atractylodes lanceaKNApSAcK Database
Capparis flavicansKNApSAcK Database
Cassytha filiformisKNApSAcK Database
Citrus unshiuKNApSAcK Database
Codonopsis tangshen OLIV.KNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
Crocus sativusKNApSAcK Database
Cucumis sativus L.KNApSAcK Database
Dioscorea oppositaKNApSAcK Database
Fritillaria cirrhosaKNApSAcK Database
Gastrodia elataKNApSAcK Database
Houttuynia cordataKNApSAcK Database
Lupinus albusKNApSAcK Database
Oxytropis myriophyllaKNApSAcK Database
Strychnos lucidaKNApSAcK Database
Triticum aestivumKNApSAcK Database
Zea mays L.KNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point235.5 °CNot Available
Boiling Point676.27 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility37 mg/mLHuman Metabolome Project
LogP-1.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
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
External Links
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
Good Scents IDrw1136651
References
General References
  1. 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 ]
  2. Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
  3. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  4. Skalhegg BS, Funderud A, Henanger HH, Hafte TT, Larsen AC, Kvissel AK, Eikvar S, Orstavik S: Protein kinase A (PKA)--a potential target for therapeutic intervention of dysfunctional immune cells. Curr Drug Targets. 2005 Sep;6(6):655-64. [PubMed:16178799 ]
  5. Maytin M, Colucci WS: Cardioprotection: a new paradigm in the management of acute heart failure syndromes. Am J Cardiol. 2005 Sep 19;96(6A):26G-31G. [PubMed:16181820 ]
  6. Dodge-Kafka KL, Soughayer J, Pare GC, Carlisle Michel JJ, Langeberg LK, Kapiloff MS, Scott JD: The protein kinase A anchoring protein mAKAP coordinates two integrated cAMP effector pathways. Nature. 2005 Sep 22;437(7058):574-8. [PubMed:16177794 ]
  7. Gheorghiade M, Teerlink JR, Mebazaa A: Pharmacology of new agents for acute heart failure syndromes. Am J Cardiol. 2005 Sep 19;96(6A):68G-73G. [PubMed:16181825 ]
  8. Jansen RW, Kruijt JK, van Berkel TJ, Meijer DK: Coupling of the antiviral drug ara-AMP to lactosaminated albumin leads to specific uptake in rat and human hepatocytes. Hepatology. 1993 Jul;18(1):146-52. [PubMed:7686877 ]
  9. Ballantyne PJ: Social context and outcomes for the ageing breast cancer patient: considerations for clinical practitioners. J Clin Nurs. 2004 Mar;13(3a):11-21. [PubMed:15028034 ]
  10. Yamamoto T, Moriwaki Y, Takahashi S, Fujita T, Tsutsumi Z, Yamakita J, Shimizu K, Shiota M, Ohta S, Higashino K: Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):55-61. [PubMed:9869364 ]
  11. Koeris M, Funke L, Shrestha J, Rich A, Maas S: Modulation of ADAR1 editing activity by Z-RNA in vitro. Nucleic Acids Res. 2005 Sep 21;33(16):5362-70. Print 2005. [PubMed:16177183 ]
  12. Vidotto C, Fousert D, Akkermann M, Griesmacher A, Muller MM: Purine and pyrimidine metabolites in children's urine. Clin Chim Acta. 2003 Sep;335(1-2):27-32. [PubMed:12927681 ]
  13. Dunne VG, Bhattachayya S, Besser M, Rae C, Griffin JL: Metabolites from cerebrospinal fluid in aneurysmal subarachnoid haemorrhage correlate with vasospasm and clinical outcome: a pattern-recognition 1H NMR study. NMR Biomed. 2005 Feb;18(1):24-33. [PubMed:15455468 ]