Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:24 UTC
HMDB IDHMDB01366
Secondary Accession NumbersNone
Metabolite Identification
Common NamePurine
DescriptionPurine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Two of the bases in nucleic acids, adenine and guanine, are purines. Purines from food (or from tissue turnover) are metabolised by several enzymes, including xanthine oxidase, into uric acid. High levels of uric acid can predispose to gout when the acid crystalises in joints; this phenomenon only happens in humans and some animal species (e.g. dogs) that lack an intrinsic uricase enzyme that can further degrade uric acid.
Structure
Thumb
Synonyms
  1. 1H-Purine
  2. 6H-Imidazo[4,5-D]pyrimidine
  3. 7-Methyltheophylline
  4. 7H-Imidazo(4,5-D)pyrimidine
  5. 7H-Purine
  6. 9H-Purine
  7. beta-Purine
  8. Caffedrine
  9. Caffein
  10. Cafipel
  11. Coffeine
  12. Dasin
  13. Dexitac
  14. Diurex
  15. Durvitan
  16. Imidazo(4,5-D)pyrimidine
  17. Isopurine
  18. Koffein
  19. Mateina
  20. Methyltheobromine
  21. Phensal
  22. Propoxyphene Compound 65
  23. Purine
  24. {6H-Imidazo[4,5-D]pyrimidine}
  25. {7H-Imidazo[4,} 5-D]pyrimidine
  26. {Imidazo[4,5-D]pyrimidine}
Chemical FormulaC5H4N4
Average Molecular Weight120.1121
Monoisotopic Molecular Weight120.043596148
IUPAC Name7H-purine
Traditional IUPAC Namepurine
CAS Registry Number120-73-0
SMILES
N1C=NC2=C1C=NC=N2
InChI Identifier
InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)
InChI KeyKDCGOANMDULRCW-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazopyrimidines
Sub ClassN/A
Other Descriptors
  • Purines and Purine Derivatives
  • a ring(Cyc)
  • purine(ChEBI)
Substituents
  • Imidazole
  • Pyrimidine
Direct ParentImidazopyrimidines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
  • Component of Purine metabolism
  • Component of Pyrimidine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500.0 mg/mLNot Available
LogP-0.37HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility53.5 g/LALOGPS
logP-0.19ALOGPS
logP-0.34ChemAxon
logS-0.35ALOGPS
pKa (strongest acidic)9.31ChemAxon
pKa (strongest basic)4.24ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area54.46ChemAxon
rotatable bond count0ChemAxon
refractivity33.21ChemAxon
polarizability10.9ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fetus
  • Fibroblasts
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB007311
KNApSAcK IDNot Available
Chemspider ID1015
KEGG Compound IDC15587
BioCyc IDPurine-Related
BiGG IDNot Available
Wikipedia LinkPurine
NuGOwiki LinkHMDB01366
Metagene LinkHMDB01366
METLIN ID6193
PubChem Compound1044
PDB IDNot Available
ChEBI ID17258
References
Synthesis ReferenceBeaman, Alden G. New synthesis of purine. Journal of the American Chemical Society (1954), 76 5633-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gudbjornsson B, Zak A, Niklasson F, Hallgren R: Hypoxanthine, xanthine, and urate in synovial fluid from patients with inflammatory arthritides. Ann Rheum Dis. 1991 Oct;50(10):669-72. Pubmed: 1958086
  2. Yamamoto T, Moriwaki Y, Cheng J, Takahashi S, Tsutsumi Z, Ka T, Hada T: Effect of inosine on the plasma concentration of uridine and purine bases. Metabolism. 2002 Apr;51(4):438-42. Pubmed: 11912550
  3. van Os S, de Abreu R, Hopman J, Wethly K, Liem D, van de Bor M: Purine and pyrimidine metabolism and electrocortical brain activity during hypoxemia in near-term lambs. Pediatr Res. 2004 Jun;55(6):1018-25. Epub 2004 Mar 17. Pubmed: 15028845
  4. Yegutkin GG, Samburski SS, Jalkanen S: Soluble purine-converting enzymes circulate in human blood and regulate extracellular ATP level via counteracting pyrophosphatase and phosphotransfer reactions. FASEB J. 2003 Jul;17(10):1328-30. Epub 2003 May 20. Pubmed: 12759341
  5. Nakashima K, Inoue K, Mayahara K, Kuroda N, Hamachi Y, Akiyama S: Use of 3-(1,8-naphthalimido)propyl-modified silyl silica gel as a stationary phase for the high-performance liquid chromatographic separation of purine derivatives. J Chromatogr A. 1996 Jan 26;722(1-2):107-13. Pubmed: 9019292
  6. Schmidt H, Siems WG, Grune T, Grauel EL: Concentration of purine compounds in the cerebrospinal fluid of infants suffering from sepsis, convulsions and hydrocephalus. J Perinat Med. 1995;23(3):167-74. Pubmed: 8568608
  7. Lyoo IK, Demopulos CM, Hirashima F, Ahn KH, Renshaw PF: Oral choline decreases brain purine levels in lithium-treated subjects with rapid-cycling bipolar disorder: a double-blind trial using proton and lithium magnetic resonance spectroscopy. Bipolar Disord. 2003 Aug;5(4):300-6. Pubmed: 12895208
  8. Burnstock G: Purine-mediated signalling in pain and visceral perception. Trends Pharmacol Sci. 2001 Apr;22(4):182-8. Pubmed: 11282418
  9. Witte DP, Wiginton DA, Hutton JJ, Aronow BJ: Coordinate developmental regulation of purine catabolic enzyme expression in gastrointestinal and postimplantation reproductive tracts. J Cell Biol. 1991 Oct;115(1):179-90. Pubmed: 1918135
  10. Shore PM, Jackson EK, Wisniewski SR, Clark RS, Adelson PD, Kochanek PM: Vascular endothelial growth factor is increased in cerebrospinal fluid after traumatic brain injury in infants and children. Neurosurgery. 2004 Mar;54(3):605-11; discussion 611-2. Pubmed: 15028134

Enzymes

Gene Name:
PYGL
Uniprot ID:
P06737
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Nebularine + Phosphoric acid unknown Purine + Ribose 1-phosphatedetails