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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 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 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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogP-0.37HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker117.69630932474
[M+H]+Baker125.40430932474
[M+H]+MetCCS_train_pos121.82130932474
[M-H]-Not Available114.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000470
[M+H]+Not Available122.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000470
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.66531661259
DarkChem[M-H]-119.85231661259
AllCCS[M+H]+124.87332859911
AllCCS[M-H]-118.98732859911
DeepCCS[M+H]+121.70230932474
DeepCCS[M-H]-119.55230932474
DeepCCS[M-2H]-155.71130932474
DeepCCS[M+Na]+130.4130932474
AllCCS[M+H]+124.932859911
AllCCS[M+H-H2O]+119.932859911
AllCCS[M+NH4]+129.532859911
AllCCS[M+Na]+130.932859911
AllCCS[M-H]-119.032859911
AllCCS[M+Na-2H]-120.632859911
AllCCS[M+HCOO]-122.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PurineN1C=NC2=C1C=NC=N21880.0Standard polar33892256
PurineN1C=NC2=C1C=NC=N21468.9Standard non polar33892256
PurineN1C=NC2=C1C=NC=N21510.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Purine,1TMS,isomer #1C[Si](C)(C)N1C=NC2=NC=NC=C211633.8Semi standard non polar33892256
Purine,1TMS,isomer #1C[Si](C)(C)N1C=NC2=NC=NC=C211513.0Standard non polar33892256
Purine,1TMS,isomer #1C[Si](C)(C)N1C=NC2=NC=NC=C212203.8Standard polar33892256
Purine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC=C211864.3Semi standard non polar33892256
Purine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC=C211702.0Standard non polar33892256
Purine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC2=NC=NC=C212313.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Purine GC-MS (1 TMS)splash10-00bc-2900000000-8bbe14cf4058a9bc94202014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Purine GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a172014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Purine GC-MS (Non-derivatized)splash10-00bc-2900000000-8bbe14cf4058a9bc94202017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Purine GC-MS (Non-derivatized)splash10-00di-3900000000-6b8938d2bbbee40f6a172017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Purine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9700000000-9fde562178115fccca672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Purine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Purine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-1bb6bb439d7ee74dcf962012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00r6-9300000000-674d58077d0065232da12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9200000000-ab847650cb6ad59c196c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-00di-0900000000-ff62b6d92894668a03072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-0900000000-d8026e115fe2859351ae2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00dl-9800000000-be78a482ed145df398c12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-014l-9100000000-42d536cf067b538a19192012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-9000000000-3932e029462a9f1d2b5b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine , negative-QTOFsplash10-014i-0900000000-84e32e7931ca8e4fb0b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-ff62b6d92894668a03072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-d8026e115fe2859351ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ , positive-QTOFsplash10-00dl-9800000000-be78a482ed145df398c12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ , positive-QTOFsplash10-014l-9100000000-42d536cf067b538a19192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine LC-ESI-QQ , positive-QTOFsplash10-014i-9000000000-3932e029462a9f1d2b5b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine , positive-QTOFsplash10-00di-0900000000-74590b66ceba02ef21522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine 20V, Positive-QTOFsplash10-00dl-6900000000-968f8ed9b4c9950772412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine 40V, Positive-QTOFsplash10-014l-9000000000-d39bf7e036895fda89852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine 10V, Positive-QTOFsplash10-00di-0900000000-7f69f5e742fdd45ce4b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Purine 35V, Positive-QTOFsplash10-00di-5900000000-f80e72eda92e7ca69c382021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 10V, Positive-QTOFsplash10-00di-2900000000-a2b7838df1b649a1e7482015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 20V, Positive-QTOFsplash10-00di-3900000000-360e26c74400d9eb73a42015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 40V, Positive-QTOFsplash10-00kf-9000000000-272193771fe6094752a52015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 10V, Negative-QTOFsplash10-014i-0900000000-c6feace15cc66f5a41572015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 20V, Negative-QTOFsplash10-014i-1900000000-028e110d0b58e5cc3f3a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purine 40V, Negative-QTOFsplash10-00kf-9100000000-a67a6fbb82af8e2a8be02015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>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 IDC00000095
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
MarkerDB IDNot Available
Good Scents IDrw1279341
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

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