Human Metabolome Database Version 3.5

Showing metabocard for Adenosine (HMDB00050)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:49 -0700
HMDB ID HMDB00050
Secondary Accession Numbers
  • HMDB04401
  • HMDB04402
  • HMDB04421
Metabolite Identification
Common Name Adenosine
Description Adenosine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H13N5O4
Average Molecular Weight 267.2413
Monoisotopic Molecular Weight 267.096753929
IUPAC Name (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name adenosine
CAS Registry Number 58-61-7
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 Key OIRDTQYFTABQOQ-KQYNXXCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class N/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 Parent Purine Nucleosides and Analogues
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Methionine metabolism
  • Component of Purine metabolism
  • Component of Selenoamino acid metabolism
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 235.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 37 mg/mL Human Metabolome Project
LogP -1.05 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 14 g/L ALOGPS
LogP -1.21 ALOGPS
LogP -2.1 ChemAxon
LogS -1.28 ALOGPS
pKa (strongest acidic) 12.45 ChemAxon
pKa (strongest basic) 4.99 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 139.54 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 63.2 ChemAxon
Polarizability 25.04 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Lysosome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.505 +/- 0.142 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
5.66 +/- 1.71 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.285 +/- 0.060 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.2 (0.1-0.3) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.0425 +/- 0.0029 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.31 +/- 0.29 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cellular Cytoplasm Detected and Quantified
1.20 (0.90-1.50) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.01 +/- 0.002 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 0.1 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.17 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.4 (0.9-2.3) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
4.7+/-7.0 umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
17.5+/-14.6 umol/mmol creatinine Children (1-13 year old) Not Specified Normal
Urine Detected and Quantified
0.50 (0.09-0.92) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.126 +/- 0.018 uM Adult (>18 years old) Both Septic 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 Link_out
      Associated OMIM IDs None
      DrugBank ID DB00640 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB003554
      KNApSAcK ID C00007444 Link_out
      Chemspider ID 54923 Link_out
      KEGG Compound ID C00212 Link_out
      BioCyc ID ADENOSINE Link_out
      BiGG ID 34273 Link_out
      Wikipedia Link Adenosine Link_out
      NuGOwiki Link HMDB00050 Link_out
      Metagene Link HMDB00050 Link_out
      METLIN ID 86 Link_out
      PubChem Compound 60961 Link_out
      PDB ID ADN Link_out
      ChEBI ID 16335 Link_out
      References
      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)
      General References
      1. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. 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 Link_out
      7. 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 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: 5'-nucleotidase
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5E
      Uniprot ID: P21589 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 1B
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5C1B
      Uniprot ID: Q96P26 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 1A
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5C1A
      Uniprot ID: Q9BXI3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, cytosolic type
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5C
      Uniprot ID: Q8TCD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Deoxycytidine kinase
      Reactions:
      Adenosine triphosphate + Adenosine unknown ADP + Adenosine monophosphate details
      Gene Name: DCK
      Uniprot ID: P27707 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, mitochondrial
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5M
      Uniprot ID: Q9NPB1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine kinase
      Reactions:
      Adenosine triphosphate + Adenosine unknown ADP + Adenosine monophosphate details
      Gene Name: ADK
      Uniprot ID: P55263 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative adenosylhomocysteinase 3
      Reactions:
      S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
      Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteine details
      Gene Name: AHCYL2
      Uniprot ID: Q96HN2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosylhomocysteinase
      Reactions:
      S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
      Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteine details
      Gene Name: AHCY
      Uniprot ID: P23526 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative adenosylhomocysteinase 2
      Reactions:
      S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
      Se-Adenosylselenohomocysteine + Water unknown Adenosine + Selenohomocysteine details
      Gene Name: AHCYL1
      Uniprot ID: O43865 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine deaminase
      Reactions:
      Adenosine + Water unknown Inosine + Ammonia details
      Gene Name: ADA
      Uniprot ID: P00813 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine receptor A1
      Reactions: Not Available
      Gene Name: ADORA1
      Uniprot ID: P30542 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine receptor A2a
      Reactions: Not Available
      Gene Name: ADORA2A
      Uniprot ID: P29274 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine receptor A3
      Reactions: Not Available
      Gene Name: ADORA3
      Uniprot ID: P33765 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine receptor A2b
      Reactions: Not Available
      Gene Name: ADORA2B
      Uniprot ID: P29275 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 3
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5C3
      Uniprot ID: Q9H0P0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine 3'-phospho 5'-phosphosulfate transporter 1
      Reactions: Not Available
      Gene Name: SLC35B2
      Uniprot ID: Q8TB61 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic purine 5'-nucleotidase
      Reactions:
      Adenosine monophosphate + Water unknown Adenosine + Phosphoric acid details
      Gene Name: NT5C2
      Uniprot ID: P49902 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Purine nucleoside phosphorylase
      Reactions:
      Adenosine + Phosphoric acid unknown Adenine + Ribose 1-phosphate details
      Gene Name: PNP
      Uniprot ID: P00491 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine 3'-phospho 5'-phosphosulfate transporter 2
      Reactions: Not Available
      Gene Name: SLC35B3
      Uniprot ID: Q9H1N7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine deaminase CECR1
      Reactions:
      Adenosine + Water unknown Inosine + Ammonia details
      Gene Name: CECR1
      Uniprot ID: Q9NZK5 Link_out
      Protein Sequence: FASTA