Human Metabolome Database Version 3.5

Showing metabocard for Purine (HMDB01366)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:24 -0700
HMDB ID HMDB01366
Secondary Accession Numbers None
Metabolite Identification
Common Name Purine
Description Purine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C5H4N4
Average Molecular Weight 120.1121
Monoisotopic Molecular Weight 120.043596148
IUPAC Name 7H-purine
Traditional IUPAC Name purine
CAS Registry Number 120-73-0
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 Key KDCGOANMDULRCW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class N/A
Other Descriptors
  • Purines and Purine Derivatives
  • a ring(Cyc)
  • purine(ChEBI)
Substituents
  • Imidazole
  • Pyrimidine
Direct Parent Imidazopyrimidines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
  • Component of Purine metabolism
  • Component of Pyrimidine metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 214 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 500.0 mg/mL Not Available
LogP -0.37 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 53.5 g/L ALOGPS
LogP -0.19 ALOGPS
LogP -0.34 ChemAxon
LogS -0.35 ALOGPS
pKa (strongest acidic) 9.31 ChemAxon
pKa (strongest basic) 4.24 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.46 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 33.21 ChemAxon
Polarizability 10.9 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
13C NMR 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-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 GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Epidermis
  • Brain
  • Myelin
  • Prostate
  • Fetus
  • Adipose Tissue
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Spleen
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
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 FDB007311
KNApSAcK ID Not Available
Chemspider ID 1015 Link_out
KEGG Compound ID C15587 Link_out
BioCyc ID Purine-Related Link_out
BiGG ID Not Available
Wikipedia Link Purine Link_out
NuGOwiki Link HMDB01366 Link_out
Metagene Link HMDB01366 Link_out
METLIN ID 6193 Link_out
PubChem Compound 1044 Link_out
PDB ID Not Available
ChEBI ID 17258 Link_out
References
Synthesis Reference Beaman, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. Burnstock G: Purine-mediated signalling in pain and visceral perception. Trends Pharmacol Sci. 2001 Apr;22(4):182-8. Pubmed: 11282418 Link_out
  7. 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 Link_out
  8. 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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Glycogen phosphorylase, liver form
Reactions: Not Available
Gene Name: PYGL
Uniprot ID: P06737 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Purine nucleoside phosphorylase
Reactions:
Nebularine + Phosphoric acid unknown Purine + Ribose 1-phosphate details
Gene Name: PNP
Uniprot ID: P00491 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA