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Purine (M2MDB000356)

Record Information
Version2.0
Creation Date2012-05-31 13:50:54 -0600
Update Date2015-09-13 15:15:23 -0600
Secondary Accession Numbers
  • ECMDB01366
Identification
Name:Purine
DescriptionPurine is a member of the chemical class known as Purines and Purine Derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. A purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature. Purines and pyrimidines make up the two groups of nitrogenous bases, including the two groups of nucleotide bases. Two of the four deoxyribonucleotides and two of the four ribonucleotides, the respective building-blocks of DNA and RNA, are purines. Purine is invovled in microbial metabolism in diverse environments.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1,3,7-Trimethyl-2,6-dioxopurine
  • 1,3,7-Trimethylxanthine
  • 1H-Purine
  • 3,5, 7-Triazaindole
  • 3,7-Dihydro-1,3,7-trimethyl-1H-Purine-2,6-dione
  • 6H-Imidazo[4,5-D]pyrimidine
  • 7-Methyltheophylline
  • 7H-Imidazo(4,5-D)pyrimidine
  • 7H-Purine
  • 9H-Purine
  • 9H-Purine (VAN)
  • Alert-Pep
  • b-Purine
  • Beta-Purine
  • Cafeina
  • Caffedrine
  • Caffein
  • Caffeine
  • Cafipel
  • CFF
  • Coffeine
  • Dasin
  • Dexitac
  • DHCplus
  • Diurex
  • Durvitan
  • Guaranine
  • Hycomine
  • Imidazo(4,5-D)pyrimidine
  • Isopurine
  • Koffein
  • Mateina
  • Methyltheobromine
  • Miudol
  • No-Doz
  • Phensal
  • Propoxyphene Compound 65
  • Purine
  • Refresh'N
  • SK 65 Compound
  • Thein
  • {6H-Imidazo[4,5-D]pyrimidine}
  • {7H-Imidazo[4,} 5-D]pyrimidine
  • {Imidazo[4,5-D]pyrimidine}
  • β-Purine
Chemical Formula:C5H4N4
Weight:Average: 120.1121
Monoisotopic: 120.043596148
InChI Key:KDCGOANMDULRCW-UHFFFAOYSA-N
InChI:InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)
CAS number:120-73-0
IUPAC Name:7H-purine
Traditional IUPAC Name:purine
SMILES:N1C=NC2=C1C=NC=N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:214 °C
Experimental Properties:
PropertyValueSource
Water Solubility:500.0 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-0.123PhysProp
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)2.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.21 m³·mol⁻¹ChemAxon
Polarizability10.9 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Purine nucleoside + Inorganic phosphate > Purine + Ribose-1-phosphate
Purine nucleoside + Phosphate + Purine deoxyribonucleoside <> Purine + Ribose-1-phosphate + Deoxyribose 1-phosphate
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00bc-2900000000-8bbe14cf4058a9bc9420View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a17View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00bc-2900000000-8bbe14cf4058a9bc9420View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a17View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9700000000-9fde562178115fccca67View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-1bb6bb439d7ee74dcf96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00r6-9300000000-674d58077d0065232da1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-ab847650cb6ad59c196cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-ff62b6d92894668a0307View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-d8026e115fe2859351aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dl-9800000000-be78a482ed145df398c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014l-9100000000-42d536cf067b538a1919View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-3932e029462a9f1d2b5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-84e32e7931ca8e4fb0b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-ff62b6d92894668a0307View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-d8026e115fe2859351aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9800000000-be78a482ed145df398c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9100000000-42d536cf067b538a1919View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-3932e029462a9f1d2b5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-74590b66ceba02ef2152View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-6900000000-968f8ed9b4c995077241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-d39bf7e036895fda8985View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7f69f5e742fdd45ce4b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-5900000000-f80e72eda92e7ca69c38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-a2b7838df1b649a1e748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-360e26c74400d9eb73a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-272193771fe6094752a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c6feace15cc66f5a4157View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-028e110d0b58e5cc3f3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-a67a6fbb82af8e2a8be0View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Burnstock G: Purine-mediated signalling in pain and visceral perception. Trends Pharmacol Sci. 2001 Apr;22(4):182-8. Pubmed: 11282418
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
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
External Links:
ResourceLink
CHEBI ID17258
HMDB IDHMDB01366
Pubchem Compound ID1044
Kegg IDC15587
ChemSpider ID1015
WikipediaPurine
BioCyc IDPURINE-RING
EcoCyc IDPURINE-RING

Enzymes

Protein Details
1. Purine nucleoside phosphorylase deoD-type
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular weight:
25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate.

Transporters

Protein Details
1. Putative purine permease ybbY
General function:
Involved in transporter activity
Specific function:
Specific function unknown
Gene Name:
ybbY
Uniprot ID:
P77328
Molecular weight:
47239
Protein Details
2. Putative purine permease ygfU
General function:
Involved in transport
Specific function:
Specific function unknown
Gene Name:
ygfU
Uniprot ID:
Q46821
Molecular weight:
51758