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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:56:06 UTC
HMDB IDHMDB0001366
Secondary Accession Numbers
  • HMDB01366
Metabolite Identification
Common NamePurine
DescriptionPurine, also known as purine base or 1H-purine, 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. 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. Purine is a moderately basic compound (based on its pKa). Purine exists in all living species, ranging from bacteria to humans. 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. In humans, purine is involved in thioguanine action pathway. Outside of the human body, Purine is found, on average, in the highest concentration within cocoa beans. Purine has also been detected, but not quantified in, several different foods, such as rapinis, plains prickly pears, blackcurrants, radish, and parsley. This could make purine a potential biomarker for the consumption of these foods. Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring.
Structure
Data?1582752195
Synonyms
ValueSource
Purine baseChEBI
1H-PurineHMDB
6H-Imidazo[4,5-D]pyrimidineHMDB
7-MethyltheophyllineHMDB
7H-Imidazo(4,5-D)pyrimidineHMDB
7H-PurineHMDB
9H-PurineHMDB
beta-PurineHMDB
CaffedrineHMDB
CaffeinHMDB
CafipelHMDB
CoffeineHMDB
DasinHMDB
DexitacHMDB
DiurexHMDB
DurvitanHMDB
Imidazo(4,5-D)pyrimidineHMDB
IsopurineHMDB
KoffeinHMDB
MateinaHMDB
MethyltheobromineHMDB
PhensalHMDB
Propoxyphene compound 65HMDB
{6h-imidazo[4,5-D]pyrimidine}HMDB
{7h-imidazo[4,} 5-D]pyrimidineHMDB
{Imidazo[4,5-D]pyrimidine}HMDB
Chemical FormulaC5H4N4
Average Molecular Weight120.1121
Monoisotopic Molecular Weight120.043596148
IUPAC Name7H-purine
Traditional 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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 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)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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00bc-2900000000-8bbe14cf4058a9bc9420Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a17Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00bc-2900000000-8bbe14cf4058a9bc9420Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9700000000-9fde562178115fccca67Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-1bb6bb439d7ee74dcf96Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00r6-9300000000-674d58077d0065232da1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-ab847650cb6ad59c196cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-ff62b6d92894668a0307Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-d8026e115fe2859351aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dl-9800000000-be78a482ed145df398c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014l-9100000000-42d536cf067b538a1919Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-3932e029462a9f1d2b5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-84e32e7931ca8e4fb0b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-ff62b6d92894668a0307Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-d8026e115fe2859351aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9800000000-be78a482ed145df398c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9100000000-42d536cf067b538a1919Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-3932e029462a9f1d2b5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-74590b66ceba02ef2152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-a2b7838df1b649a1e748Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-360e26c74400d9eb73a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-272193771fe6094752a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c6feace15cc66f5a4157Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-028e110d0b58e5cc3f3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-a67a6fbb82af8e2a8be0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007311
KNApSAcK IDNot Available
Chemspider ID1015
KEGG Compound IDC15587
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPurine
METLIN ID6193
PubChem Compound1044
PDB IDNot Available
ChEBI ID17258
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  6. Burnstock G: Purine-mediated signalling in pain and visceral perception. Trends Pharmacol Sci. 2001 Apr;22(4):182-8. [PubMed:11282418 ]
  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 ]
  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 ]
  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

General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Nebularine + Phosphate → Purine + Ribose 1-phosphatedetails