Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:33 UTC
HMDB IDHMDB00034
Secondary Accession NumbersNone
Metabolite Identification
Common NameAdenine
DescriptionAdenine 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 , 229600 , 603027 , 232400 , 232600 , 232800 , 201450 , 220150 , 232200 , 162000 , 164050 , 278300 ). (PMID: 17052198 , 17520339 ).
Structure
Thumb
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 FormulaC5H5N5
Average Molecular Weight135.1267
Monoisotopic Molecular Weight135.054495185
IUPAC Name7H-purin-6-amine
Traditional IUPAC Nameadenine
CAS Registry Number73-24-5
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 KeyGFFGJBXGBJISGV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazopyrimidines
Sub ClassN/A
Other Descriptors
  • 6-aminopurines(ChEBI)
  • Purines and Purine Derivatives
  • Purines(KEGG)
  • a ring(Cyc)
  • purine nucleobase(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Pyrimidine
Direct ParentImidazopyrimidines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • DNA component
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.03 mg/mLNot Available
LogP-0.09HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility11.5 g/LALOGPS
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (strongest acidic)10.29ChemAxon
pKa (strongest basic)5.32ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area80.48ChemAxon
rotatable bond count0ChemAxon
refractivity38.22ChemAxon
polarizability12.29ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
  • Lysosome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.3 +/- 0.1 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified 0.64 +/- 0.15 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.2 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.65 (0.52-0.85) umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified2.9 (1.4-5.1) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified1.17 umol/mmol creatinineAdult (>18 years old)MaleCommentNormal
  • Shaykhutdino...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.5 +/- 0.3 uMAdult (>18 years old)BothSolid tumors
Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0 - 18.0) uMChildren (1-13 year old)Not SpecifiedCommentMeningitis
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 (0 - 23.4) uMChildren (1-13 year old)Not SpecifiedTuberculous meningitis
Cerebrospinal Fluid (CSF)Detected and Quantified0.96 (0 - 12.0) uMChildren (1-13 year old)Not SpecifiedCommentMeningitis
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
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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012266
KNApSAcK IDC00001490
Chemspider ID185
KEGG Compound IDC00147
BioCyc IDADENINE
BiGG ID34039
Wikipedia LinkAdenine
NuGOwiki LinkHMDB00034
Metagene LinkHMDB00034
METLIN ID85
PubChem Compound190
PDB IDADE
ChEBI ID16708
References
Synthesis ReferenceBaddiley, 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)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. Rolfes RJ: Regulation of purine nucleotide biosynthesis: in yeast and beyond. Biochem Soc Trans. 2006 Nov;34(Pt 5):786-90. Pubmed: 17052198
  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

Enzymes

Gene Name:
XDH
Uniprot ID:
P47989
Gene Name:
MTAP
Uniprot ID:
Q13126
Reactions
5'-Methylthioadenosine + Phosphoric acid unknown Adenine + 5-Methylthioribose 1-phosphatedetails
Gene Name:
APRT
Uniprot ID:
P07741
Reactions
Adenosine monophosphate + Pyrophosphate unknown Adenine + Phosphoribosyl pyrophosphatedetails
Gene Name:
HPRT1
Uniprot ID:
P00492
Reactions
Adenosine monophosphate + Pyrophosphate unknown Adenine + Phosphoribosyl pyrophosphatedetails
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Gene Name:
SLC29A3
Uniprot ID:
Q9BZD2
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Adenosine + Phosphoric acid unknown Adenine + Ribose 1-phosphatedetails
Deoxyadenosine + Phosphoric acid unknown Adenine + Deoxyribose 1-phosphatedetails