Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:49 UTC
HMDB IDHMDB00050
Secondary Accession Numbers
  • HMDB04401
  • HMDB04402
  • HMDB04421
Metabolite 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. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent.
Structure
Thumb
Synonyms
  1. 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-Ribofuranose
  2. 1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-Ribofuranose
  3. 6-Amino-9beta-D-ribofuranosyl-9H-purine
  4. 6-Amino-9beta-delta-ribofuranosyl-9H-purine
  5. 9-beta-D-Arabinofuranosyladenine
  6. 9-beta-D-Ribofuranosidoadenine
  7. 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  8. 9-beta-D-Ribofuranosyladenine
  9. 9-beta-delta-Arabinofuranosyladenine
  10. 9-beta-delta-Ribofuranosidoadenine
  11. 9-beta-delta-Ribofuranosyl-9H-purin-6-amine
  12. 9-beta-delta-Ribofuranosyladenine
  13. 9beta-D-ribofuranosyl-9H-Purin-6-amine
  14. 9beta-D-Ribofuranosyladenine
  15. 9beta-delta-ribofuranosyl-9H-Purin-6-amine
  16. 9beta-delta-Ribofuranosyladenine
  17. Adenine nucleoside
  18. Adenine riboside
  19. Adenine-9beta-D-Ribofuranoside
  20. Adenine-9beta-delta-Ribofuranoside
  21. Adenocard
  22. Adenocor
  23. Adenoscan
  24. Adenosin
  25. b-D-Adenosine
  26. beta-Adenosine
  27. beta-D-Adenosine
  28. beta-delta-Adenosine
  29. Boniton
  30. Myocol
  31. Nucleocardyl
  32. Sandesin
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 IUPAC Nameadenosine
CAS Registry Number58-61-7
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
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
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleosides and Analogues
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Ribonucleosides(KEGG)
  • adenosines(ChEBI)
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Nucleosides and Analogues
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Methionine metabolism
  • Component of Purine metabolism
  • Component of Selenoamino acid metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Lysosome
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
water solubility14 g/LALOGPS
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 area139.54ChemAxon
rotatable bond count2ChemAxon
refractivity63.2ChemAxon
polarizability25.04ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Lysosome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.505 +/- 0.142 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified5.66 +/- 1.71 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.285 +/- 0.060 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.2 (0.1-0.3) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.0425 +/- 0.0029 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.31 +/- 0.29 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified1.20 (0.90-1.50) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.1 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.17 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified1.4 (0.9-2.3) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified4.7+/-7.0 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified17.5+/-14.6 umol/mmol creatinineChildren (1-13 year old)Not SpecifiedNormal
UrineDetected and Quantified0.50 (0.09-0.92) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.126 +/- 0.018 uMAdult (>18 years old)BothSeptic shock
Associated Disorders and Diseases
Disease References
Septic shock
  • Kaufmann I, Hoelzl A, Schliephake F, Hummel T, Chouker A, Lysenko L, Peter K, Thiel M: Effects of adenosine on functions of polymorphonuclear leukocytes from patients with septic shock. Shock. 2007 Jan;27(1):25-31. Pubmed: 17172976
Associated OMIM IDsNone
DrugBank IDDB00640
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003554
KNApSAcK IDC00007444
Chemspider ID54923
KEGG Compound IDC00212
BioCyc IDADENOSINE
BiGG ID34273
Wikipedia LinkAdenosine
NuGOwiki LinkHMDB00050
Metagene LinkHMDB00050
METLIN ID86
PubChem Compound60961
PDB IDADN
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. 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(1):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

Enzymes

Gene Name:
NT5E
Uniprot ID:
P21589
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
DCK
Uniprot ID:
P27707
Reactions
Adenosine triphosphate + Adenosine unknown ADP + Adenosine monophosphatedetails
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
ADK
Uniprot ID:
P55263
Reactions
Adenosine triphosphate + Adenosine unknown ADP + Adenosine monophosphatedetails
Gene Name:
AHCYL2
Uniprot ID:
Q96HN2
Reactions
S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosinedetails
Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteinedetails
Gene Name:
AHCY
Uniprot ID:
P23526
Reactions
S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosinedetails
Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteinedetails
Gene Name:
AHCYL1
Uniprot ID:
O43865
Reactions
S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosinedetails
Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteinedetails
Gene Name:
ADA
Uniprot ID:
P00813
Reactions
Adenosine + Water unknown Inosine + Ammoniadetails
Gene Name:
ADORA1
Uniprot ID:
P30542
Gene Name:
ADORA2A
Uniprot ID:
P29274
Gene Name:
ADORA3
Uniprot ID:
P33765
Gene Name:
ADORA2B
Uniprot ID:
P29275
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
NT5C2
Uniprot ID:
P49902
Reactions
Adenosine monophosphate + Water unknown Adenosine + Phosphoric aciddetails
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Adenosine + Phosphoric acid unknown Adenine + Ribose 1-phosphatedetails
Gene Name:
CECR1
Uniprot ID:
Q9NZK5
Reactions
Adenosine + Water unknown Inosine + Ammoniadetails