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Human Metabolome Database Version 3.5

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Showing metabocard for Adenine (HMDB00034)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:33 -0600
HMDB ID HMDB00034
Secondary Accession Numbers None
Metabolite Identification
Common Name Adenine
Description Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322 Link_out, 229600 Link_out, 603027 Link_out, 232400 Link_out, 232600 Link_out, 232800 Link_out, 201450 Link_out, 220150 Link_out, 232200 Link_out, 162000 Link_out, 164050 Link_out, 278300 Link_out). (PMID: 17052198 Link_out, 17520339 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,6-Dihydro-6-iminopurine
  2. 1H-Purin-6-amine
  3. 1H-Purine-6-amine
  4. 3,6-Dihydro-6-iminopurine
  5. 6-Amino-1H-purine
  6. 6-Amino-3H-purine
  7. 6-Amino-7H-purine
  8. 6-Amino-9H-purine
  9. 6-Amino-Purine
  10. 6-Aminopurine
  11. 9H-Purin-6-amine
  12. 9H-Purin-6-yl-amin
  13. 9H-Purin-6-ylamine
  14. 9H-Purine-6-amine
  15. Ade
  16. Adenin
  17. Adenine
  18. Adeninimine
  19. Vitamin B4
Chemical Formula C5H5N5
Average Molecular Weight 135.1267
Monoisotopic Molecular Weight 135.054495185
IUPAC Name 7H-purin-6-amine
Traditional IUPAC Name adenine
CAS Registry Number 73-24-5
SMILES NC1=NC=NC2=C1NC=N2
InChI Identifier InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
InChI Key GFFGJBXGBJISGV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class N/A
Other Descriptors
  • 6-aminopurines(ChEBI)
  • Purines and Purine Derivatives
  • Purines(KEGG)
  • a ring(Cyc)
  • purine nucleobase(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Pyrimidine
Direct Parent Imidazopyrimidines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • DNA component
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 360 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.03 mg/mL Not Available
LogP -0.09 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 11.5 g/L ALOGPS
LogP -0.38 ALOGPS
LogP -0.57 ChemAxon
LogS -1.07 ALOGPS
pKa (strongest acidic) 10.29 ChemAxon
pKa (strongest basic) 5.32 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 80.48 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 38.22 ChemAxon
Polarizability 12.29 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H 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-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
  • Prostate
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
0.3 +/- 0.1 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.64 +/- 0.15 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 0.2 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.65 (0.52-0.85) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
2.9 (1.4-5.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
1.17 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
  • Shaykhutdino...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.5 +/- 0.3 uM Adult (>18 years old) Both Solid tumors
Cerebrospinal Fluid (CSF) Detected and Quantified 0.5 (0 - 18.0) uM Children (1-13 year old) Not Specified Comment Meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.35 (0 - 23.4) uM Children (1-13 year old) Not Specified Tuberculous meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.96 (0 - 12.0) uM Children (1-13 year old) Not Specified Comment Meningitis
Associated Disorders and Diseases
Disease References
Meningitis
  • Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Neuron-specific enolase, nucleotides, nucleosides, purine bases, oxypurines and uric acid concentrations in cerebrospinal fluid of children with meningitis. Brain Dev. 2003 Mar;25(2):102-6. Pubmed: 12581805 Link_out
    Tuberculous meningitis
    • Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Neuron-specific enolase, nucleotides, nucleosides, purine bases, oxypurines and uric acid concentrations in cerebrospinal fluid of children with meningitis. Brain Dev. 2003 Mar;25(2):102-6. Pubmed: 12581805 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012266
      KNApSAcK ID C00001490 Link_out
      Chemspider ID 185 Link_out
      KEGG Compound ID C00147 Link_out
      BioCyc ID ADENINE Link_out
      BiGG ID 34039 Link_out
      Wikipedia Link Adenine Link_out
      NuGOwiki Link HMDB00034 Link_out
      Metagene Link HMDB00034 Link_out
      METLIN ID 85 Link_out
      PubChem Compound 190 Link_out
      PDB ID ADE Link_out
      ChEBI ID 16708 Link_out
      References
      Synthesis Reference Baddiley, J.; Lythgoe, B.; Todd, A. R. Synthesis of purine nucleosides. II. A new and convenient synthesis of adenine. Journal of the Chemical Society (1943), 386-7.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Moriyama H, Iizuka T, Nagai M, Hoshi K: Adenine, an inhibitor of platelet aggregation, from the leaves of Cassia alata. Biol Pharm Bull. 2003 Sep;26(9):1361-4. Pubmed: 12951489 Link_out
      2. Liu Y, Xu G, Xu C, Garcia L, Lin CC, Yeh LT: Ultra sensitive method for the determination of 9-(2-phosphonylmethoxyethyl)adenine in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 25;803(2):293-8. Pubmed: 15063338 Link_out
      3. Terry KL, De Vivo I, Titus-Ernstoff L, Shih MC, Cramer DW: Androgen receptor cytosine, adenine, guanine repeats, and haplotypes in relation to ovarian cancer risk. Cancer Res. 2005 Jul 1;65(13):5974-81. Pubmed: 15994977 Link_out
      4. Steiner MC, Evans R, Deacon SJ, Singh SJ, Patel P, Fox J, Greenhaff PL, Morgan MD: Adenine nucleotide loss in the skeletal muscles during exercise in chronic obstructive pulmonary disease. Thorax. 2005 Nov;60(11):932-6. Epub 2005 Jul 29. Pubmed: 16055624 Link_out
      5. Di Pietro V, Perruzza I, Amorini AM, Balducci A, Ceccarelli L, Lazzarino G, Barsotti P, Giardina B, Tavazzi B: Clinical, biochemical and molecular diagnosis of a compound homozygote for the 254 bp deletion-8 bp insertion of the APRT gene suffering from severe renal failure. Clin Biochem. 2006 Oct 19;. Pubmed: 17126311 Link_out
      6. Whitehead JW, Lee GP, Gharagozloo P, Hofer P, Gehrig A, Wintergerst P, Smyth D, McCoull W, Hachicha M, Patel A, Kyle DJ: 8-Substituted analogues of 3-(3-cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-adenine: highly potent and selective PDE4 inhibitors. J Med Chem. 2005 Feb 24;48(4):1237-43. Pubmed: 15715490 Link_out
      7. Reimers HJ, Packham MA, Mustard JF: Labeling of the releasable adenine nucleotides of washed human platelets. Blood. 1977 Jan;49(1):89-99. Pubmed: 401462 Link_out
      8. Hartmann S, Okun JG, Schmidt C, Langhans CD, Garbade SF, Burgard P, Haas D, Sass JO, Nyhan WL, Hoffmann GF: Comprehensive detection of disorders of purine and pyrimidine metabolism by HPLC with electrospray ionization tandem mass spectrometry. Clin Chem. 2006 Jun;52(6):1127-37. Epub 2006 Apr 13. Pubmed: 16613999 Link_out
      9. 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
      10. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
      11. Ruiz-Stewart I, Kazerounian S, Pitari GM, Schulz S, Waldman SA: Soluble guanylate cyclase is allosterically inhibited by direct interaction with 2-substituted adenine nucleotides. Eur J Biochem. 2002 Apr;269(8):2186-93. Pubmed: 11985597 Link_out
      12. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
      13. Rolfes RJ: Regulation of purine nucleotide biosynthesis: in yeast and beyond. Biochem Soc Trans. 2006 Nov;34(Pt 5):786-90. Pubmed: 17052198 Link_out
      14. Simoni RE, Gomes LN, Scalco FB, Oliveira CP, Aquino Neto FR, de Oliveira ML: Uric acid changes in urine and plasma: an effective tool in screening for purine inborn errors of metabolism and other pathological conditions. J Inherit Metab Dis. 2007 Jun;30(3):295-309. Epub 2007 May 19. Pubmed: 17520339 Link_out
      Enzymes
      Name: Xanthine dehydrogenase/oxidase
      Reactions: Not Available
      Gene Name: XDH
      Uniprot ID: P47989 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: S-methyl-5'-thioadenosine phosphorylase
      Reactions:
      5'-Methylthioadenosine + Phosphoric acid unknown Adenine + 5-Methylthioribose 1-phosphate details
      Gene Name: MTAP
      Uniprot ID: Q13126 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenine phosphoribosyltransferase
      Reactions:
      Adenosine monophosphate + Pyrophosphate unknown Adenine + Phosphoribosyl pyrophosphate details
      Gene Name: APRT
      Uniprot ID: P07741 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Hypoxanthine-guanine phosphoribosyltransferase
      Reactions:
      Adenosine monophosphate + Pyrophosphate unknown Adenine + Phosphoribosyl pyrophosphate details
      Gene Name: HPRT1
      Uniprot ID: P00492 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Peroxisomal trans-2-enoyl-CoA reductase
      Reactions: Not Available
      Gene Name: PECR
      Uniprot ID: Q9BY49 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Equilibrative nucleoside transporter 2
      Reactions: Not Available
      Gene Name: SLC29A2
      Uniprot ID: Q14542 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Equilibrative nucleoside transporter 3
      Reactions: Not Available
      Gene Name: SLC29A3
      Uniprot ID: Q9BZD2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Purine nucleoside phosphorylase
      Reactions:
      Adenosine + Phosphoric acid unknown Adenine + Ribose 1-phosphate details
      Deoxyadenosine + Phosphoric acid unknown Adenine + Deoxyribose 1-phosphate details
      Gene Name: PNP
      Uniprot ID: P00491 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA