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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-15 21:04:29 UTC
HMDB IDHMDB0000292
Secondary Accession Numbers
  • HMDB00292
Metabolite Identification
Common NameXanthine
DescriptionXanthine, also known as 2,6-dioxopurine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Xanthine is also classified as an oxopurine. An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine exists in all living species, ranging from bacteria to plants to humans. In plants, several stimulants can be derived from xanthine, including caffeine, theophylline, and theobromine. Derivatives of xanthine (known collectively as xanthines) are a group of alkaloids commonly used for their effects as mild stimulants and as bronchodilators, notably in the treatment of asthma or influenza symptoms. Within humans, xanthine participates in a number of enzymatic reactions. In particular, xanthine can be biosynthesized from guanine; which is mediated by the enzyme guanine deaminase. In addition, xanthine and ribose 1-phosphate can be biosynthesized from xanthosine through the action of the enzyme purine nucleoside phosphorylase. In humans and other primates, xanthine can be converted to uric acid by the action of the xanthine oxidase enzyme. People with rare genetic disorders, specifically xanthinuria and Lesch-Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. Individuals with xanthinuria have unusually high concentrations of xanthine in their blood and urine, which can lead to health problems such as renal failure and xanthine kidney stones. Individuals with Lesch-Nyhan syndrome have a deficiency of the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT). The HGPRT deficiency causes a build-up of uric acid in all body fluids. This results in both high levels of uric acid in the blood and urine, associated with severe gout and kidney problems. Neurological signs include poor muscle control and moderate intellectual disability.
Structure
Data?1589493092
Synonyms
ValueSource
2,6-DihydroxypurineChEBI
2,6-Dioxo-1,2,3,6-tetrahydropurineChEBI
9H-Purine-2,6-(1H,3H)-dioneChEBI
Purine-2(3H),6(1H)-dioneChEBI
XanChEBI
1H-Purine-2,6-diolHMDB
2,6(1,3)-PurinedionHMDB
2,6-DioxopurineHMDB
3,7-Dihydro-1H-purine-2,6-dioneHMDB
3,7-Dihydropurine-2,6-dioneHMDB
9H-Purine-2,6(1H,3H)-dioneHMDB
9H-Purine-2,6-diolHMDB
DioxopurineHMDB
IsoxanthineHMDB
PseudoxanthineHMDB
Purine-2,6(1H,3H)-dioneHMDB
Purine-2,6-diolHMDB
Xanthic oxideHMDB
XanthinHMDB
Chemical FormulaC5H4N4O2
Average Molecular Weight152.1109
Monoisotopic Molecular Weight152.033425392
IUPAC Name2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namexanthine
CAS Registry Number69-89-6
SMILES
O=C1NC2=C(NC=N2)C(=O)N1
InChI Identifier
InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
InChI KeyLRFVTYWOQMYALW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)MERCK INDEX (1996); Human Metabolome Project (salt)
LogP-0.73HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg119.730932474
[M-H]-Baker124.36530932474
[M-H]-MetCCS_test_neg118.530932474
[M+H]+Baker138.10530932474
[M+H]+Astarita_pos124.330932474
[M+H]+MetCCS_test_pos130.34830932474
[M-H]-Not Available121.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000368
[M+H]+Not Available134.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000368
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.91 g/LALOGPS
logP-0.65ALOGPS
logP-0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.92 m³·mol⁻¹ChemAxon
Polarizability12.7 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]+131.50431661259
DarkChem[M-H]-128.50231661259
AllCCS[M+H]+132.57132859911
AllCCS[M-H]-125.53732859911
DeepCCS[M+H]+130.59830932474
DeepCCS[M-H]-127.23630932474
DeepCCS[M-2H]-164.47830932474
DeepCCS[M+Na]+139.62330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthineO=C1NC2=C(NC=N2)C(=O)N12748.7Standard polar33892256
XanthineO=C1NC2=C(NC=N2)C(=O)N11757.7Standard non polar33892256
XanthineO=C1NC2=C(NC=N2)C(=O)N12200.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthine,1TMS,isomer #1C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]21881.0Semi standard non polar33892256
Xanthine,1TMS,isomer #1C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]22049.2Standard non polar33892256
Xanthine,1TMS,isomer #1C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]22884.1Standard polar33892256
Xanthine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]21932.4Semi standard non polar33892256
Xanthine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]22038.2Standard non polar33892256
Xanthine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]22738.5Standard polar33892256
Xanthine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O1878.4Semi standard non polar33892256
Xanthine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O2112.9Standard non polar33892256
Xanthine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O2926.7Standard polar33892256
Xanthine,2TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O1973.3Semi standard non polar33892256
Xanthine,2TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O2121.0Standard non polar33892256
Xanthine,2TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O2493.3Standard polar33892256
Xanthine,2TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C1929.9Semi standard non polar33892256
Xanthine,2TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C2080.9Standard non polar33892256
Xanthine,2TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C2381.9Standard polar33892256
Xanthine,2TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N21956.9Semi standard non polar33892256
Xanthine,2TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N22112.8Standard non polar33892256
Xanthine,2TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N22425.3Standard polar33892256
Xanthine,3TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O2067.7Semi standard non polar33892256
Xanthine,3TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O2081.8Standard non polar33892256
Xanthine,3TMS,isomer #1C[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O2199.8Standard polar33892256
Xanthine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]22096.3Semi standard non polar33892256
Xanthine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]22274.4Standard non polar33892256
Xanthine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C[NH]22853.1Standard polar33892256
Xanthine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]22159.7Semi standard non polar33892256
Xanthine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]22267.8Standard non polar33892256
Xanthine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)[NH]22780.4Standard polar33892256
Xanthine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O2072.9Semi standard non polar33892256
Xanthine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O2293.3Standard non polar33892256
Xanthine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C=N2)C1=O2915.7Standard polar33892256
Xanthine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2285.7Semi standard non polar33892256
Xanthine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2493.9Standard non polar33892256
Xanthine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O2529.4Standard polar33892256
Xanthine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C2327.4Semi standard non polar33892256
Xanthine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C2480.7Standard non polar33892256
Xanthine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C2468.3Standard polar33892256
Xanthine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N22354.7Semi standard non polar33892256
Xanthine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N22509.6Standard non polar33892256
Xanthine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N22525.2Standard polar33892256
Xanthine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2560.5Semi standard non polar33892256
Xanthine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2729.5Standard non polar33892256
Xanthine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O2481.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Xanthine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f6t-0924000000-9b80e0a2a60c73ca01802014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Xanthine GC-EI-TOF (Non-derivatized)splash10-0f6t-0924000000-9b80e0a2a60c73ca01802017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Xanthine GC-EI-TOF (Non-derivatized)splash10-0f6t-0924000000-30dc5892eecde860846a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-7900000000-2dc30b0fc4cff2239dbe2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-2d5ab5d5db8ff49814672014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0900000000-a70539989d121bfacee02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-6900000000-b047b06406308dbaeda82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-9300000000-ed480ed920c3e9b576ec2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0zfr-0900000000-efb049914c9bce5962672012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine LC-ESI-QTOF , negative-QTOFsplash10-0zfr-0900000000-efb049914c9bce5962672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine , negative-QTOFsplash10-0udi-0900000000-5fee91293851bb02193e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine LC-ESI-IT , positive-QTOFsplash10-000i-0900000000-4568a814903ff411923a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 40V, Negative-QTOFsplash10-00kf-9000000000-e078a358156f5a04d4c12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 20V, Negative-QTOFsplash10-0a4i-3900000000-250f7dc30d6fd96a4ef62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 20V, Positive-QTOFsplash10-0ik9-0900000000-3a6dad2473c1654789f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 10V, Negative-QTOFsplash10-0udi-0900000000-a4e9443b51c3ac2fc58b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 40V, Negative-QTOFsplash10-00kf-9000000000-d23801a49488b1a5f0a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 20V, Negative-QTOFsplash10-0a4i-4900000000-b177a2a36043e5e87efc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 35V, Negative-QTOFsplash10-0udi-0900000000-cb3b35c3117b7f36bf5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 10V, Negative-QTOFsplash10-0zfr-0900000000-8d2a19e7c37d2cb7658f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 30V, Negative-QTOFsplash10-05mo-9300000000-33d00ab2288aaa0555172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 20V, Positive-QTOFsplash10-0ik9-1900000000-3a6dad2473c1654789f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 40V, Positive-QTOFsplash10-001i-9000000000-37e76df2401a85967caa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthine 35V, Negative-QTOFsplash10-0udi-0900000000-4132da06dda895afc3ab2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 10V, Positive-QTOFsplash10-0udi-0900000000-2e9e069e2df414aed0372015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 20V, Positive-QTOFsplash10-0w29-0900000000-fa52193346bc456d89e82015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 40V, Positive-QTOFsplash10-0a5i-9400000000-bbf70998e8b7515cb4402015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 10V, Negative-QTOFsplash10-0udi-0900000000-566d663553ce4f0ec2072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 20V, Negative-QTOFsplash10-0zfr-1900000000-d0a5d2c0f89f8d42d9032015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthine 40V, Negative-QTOFsplash10-0006-9000000000-351d9f8ee3470f9118292015-05-27Wishart 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)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)2022-02-11FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<1.00 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.7 +/- 0.2 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.9 +/- 0.1 uMAdult (>18 years old)Male
normal
details
BloodDetected and Quantified0.700 +/- 0.200 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.3-3 uMChildren (1-13 years old)Not SpecifiedNormal details
BloodDetected and Quantified1.27 +/- 0.78 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.289 +/- 9.211 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified4.5(2.7-8.0) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified<2 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified4.9 +/- 1.5 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.91 +/- 0.45 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified200 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified5.20 (4.33-6.07) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.5 +/- 0.7 uMChildren (1 - 13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified13 +/- 7 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified1.32 +/- 1.72 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified0.88 +/- 0.31 uMAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified1.81+/- 0.58 uMAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified1.58 +/- 0.39 uMAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified<40 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0 -30 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified15.6 +/- 1.1 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified3.279 +/- 1.0175 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified3.4 +/- 1.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.522 +/- 1.131 umol/mmol creatinineAdult (>18 years old)Male
normal
details
UrineDetected and Quantified275.753 +/- 65.914 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<30 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified<80 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified2.6 (2.2-3.75) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified3-62 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified2.667 (2.267-3.800) umol/mmol creatinineNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified52.591 +/- 67.878 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified4.3 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified<40 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified0-43 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.2 +/- 0.3 uMAdult (>18 years old)BothLesch-Nyhan syndrome details
BloodDetected and Quantified6.8 uMAdult (>18 years old)Female
Xanthinuria type 1
details
BloodDetected and Quantified12.4 uMChildren (1-13 years old)Male
Xanthinuria type 1
details
BloodDetected and Quantified118 uMAdult (>18 years old)Male
Lesch-Nyhan syndrome
details
BloodDetected and Quantified2.7 +/- 1.6 uMAdult (>18 years old)Male
Lesch-Nyhan syndrome
details
BloodDetected and Quantified9-14 uMChildren (1-13 years old)Both
Xanthinuria type 1
details
BloodDetected and Quantified1.1 uMAdult (>18 years old)FemalePhosphoribosylpyrophosphate Synthetase Superactivity details
BloodDetected and Quantified40 uMChildren (1-13 years old)MaleXanthinuria type II details
BloodDetected and Quantified51.2 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified6.37 +/- 1.95 uMAdult (>18 years old)BothCanavan disease details
BloodDetected and Quantified9.868 +/- 5.263 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified18 uMInfant (0-1 year old)FemaleMolybdenium co-factor deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified5.17 (3.64-6.70) uMAdult (>18 years old)Both
Hydrocephalus
details
Cerebrospinal Fluid (CSF)Detected and Quantified9.90 (7.46-12.3) uMChildren (1-13 years old)Both
Hydrocephalus
details
Cerebrospinal Fluid (CSF)Detected and Quantified19.6 uMChildren (1 - 13 years old)Not SpecifiedIsolated 3-Methylcrotonyl-CoA Carboxylase Deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified2.30 (2.10-2.50) uMAdult (>18 years old)BothDegenerative disc disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
SweatDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specifiedscreen-positive CF details
UrineDetected and Quantified146.978 umol/mmol creatinineAdult (>18 years old)Female
Xanthinuria type 1
details
UrineDetected and Quantified192.202 umol/mmol creatinineChildren (1-13 years old)Male
Xanthinuria type 1
details
UrineDetected and Quantified193 umol/mmol creatinineAdult (>18 years old)Male
Xanthinuria type 1
details
UrineDetected and Quantified228 umol/mmol creatinineChildren (1-13 years old)Not Specified
Molybdenum cofactor deficiency
details
UrineDetected and Quantified991 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Molybdenum cofactor deficiency
details
UrineDetected and Quantified1.6-3 umol/mmol creatinineInfant (0-1 year old)BothSulfite oxidase deficiency details
UrineDetected and Quantified12.9-34.9 umol/mmol creatinineChildren (1-13 years old)BothSulfite oxidase deficiency details
UrineDetected and Quantified164.5-349.3 umol/mmol creatinineChildren (1-13 years old)Both
Xanthinuria type 1
details
UrineDetected and Quantified31.657 +/- 19.220 umol/mmol creatinineAdult (>18 years old)Male
Lesch-Nyhan syndrome
details
UrineDetected and Quantified529-1713 umol/mmol creatinineInfant (0-1 year old)BothMolybdenum cofactor deficiency details
UrineDetected and Quantified524.146 umol/mmol creatinineAdult (>18 years old)FemalePhosphoribosylpyrophosphate Synthetase Superactivity details
UrineDetected and Quantified4.9 umol/mmol creatinineAdolescent (13-18 years old)Female
Adenosine kinase deficiency
details
UrineDetected and Quantified6.8 umol/mmol creatinineAdult (>18 years old)Male
Adenosine kinase deficiency
details
UrineDetected and Quantified37.779 +/- 61.348 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified48 umol/mmol creatinineInfant (0-1 year old)FemaleMolybdenium co-factor deficiency details
UrineDetected and Quantified259 umol/mmol creatinineChildren (1-13 years old)MaleMolybdenium co-factor deficiency details
Associated Disorders and Diseases
Disease References
Lesch-Nyhan syndrome
  1. Harkness RA, McCreanor GM, Watts RW: Lesch-Nyhan syndrome and its pathogenesis: purine concentrations in plasma and urine with metabolite profiles in CSF. J Inherit Metab Dis. 1988;11(3):239-52. [PubMed:3148065 ]
  2. Gregoric A, Rabelink GM, Kokalj Vokac N, Varda NM, Zagradisnik B: Eighteen-year follow-up of a patient with partial hypoxanthine phosphoribosyltransferase deficiency and a new mutation. Pediatr Nephrol. 2005 Sep;20(9):1346-8. Epub 2005 Jun 18. [PubMed:15965771 ]
  3. Puig JG, Torres RJ, Mateos FA, Ramos TH, Arcas JM, Buno AS, O'Neill P: The spectrum of hypoxanthine-guanine phosphoribosyltransferase (HPRT) deficiency. Clinical experience based on 22 patients from 18 Spanish families. Medicine (Baltimore). 2001 Mar;80(2):102-12. [PubMed:11307586 ]
Canavan disease
  1. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
Xanthinuria type 1
  1. Mateos FA, Puig JG, Jimenez ML, Fox IH: Hereditary xanthinuria. Evidence for enhanced hypoxanthine salvage. J Clin Invest. 1987 Mar;79(3):847-52. [PubMed:3818951 ]
  2. Mraz M, Hurba O, Bartl J, Dolezel Z, Marinaki A, Fairbanks L, Stiburkova B: Modern diagnostic approach to hereditary xanthinuria. Urolithiasis. 2015 Feb;43(1):61-7. doi: 10.1007/s00240-014-0734-4. Epub 2014 Nov 6. [PubMed:25370766 ]
  3. Eggermann T, Spengler S, Denecke B, Zerres K, Mache CJ: Multi-exon deletion in the XDH gene as a cause of classical xanthinuria. Clin Nephrol. 2013 Jan;79(1):78-80. [PubMed:23249873 ]
Xanthinuria type II
  1. Zannolli R, Micheli V, Mazzei MA, Sacco P, Piomboni P, Bruni E, Miracco C, de Santi MM, Terrosi Vagnoli P, Volterrani L, Pellegrini L, Livi W, Lucani B, Gonnelli S, Burlina AB, Jacomelli G, Macucci F, Pucci L, Fimiani M, Swift JA, Zappella M, Morgese G: Hereditary xanthinuria type II associated with mental delay, autism, cortical renal cysts, nephrocalcinosis, osteopenia, and hair and teeth defects. J Med Genet. 2003 Nov;40(11):e121. [PubMed:14627688 ]
Molybdenium co-factor deficiency
  1. Aukett A, Bennett MJ, Hosking GP: Molybdenum co-factor deficiency: an easily missed inborn error of metabolism. Dev Med Child Neurol. 1988 Aug;30(4):531-5. [PubMed:3169394 ]
  2. Nagappa M, Bindu PS, Taly AB, Sinha S, Bharath RD: Child Neurology: Molybdenum cofactor deficiency. Neurology. 2015 Dec 8;85(23):e175-8. doi: 10.1212/WNL.0000000000002194. [PubMed:26644055 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Degenerative disc disease
  1. Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
Hydrocephalus
  1. Castro-Gago M, Rodriguez IN, Rodriguez-Nunez A, Guitian JP, Rocamonde SL, Rodriguez-Segade S: Therapeutic criteria in hydrocephalic children. Childs Nerv Syst. 1989 Dec;5(6):361-3. [PubMed:2611770 ]
3-Methyl-crotonyl-glycinuria
  1. de Kremer RD, Latini A, Suormala T, Baumgartner ER, Larovere L, Civallero G, Guelbert N, Paschini-Capra A, Depetris-Boldini C, Mayor CQ: Leukodystrophy and CSF purine abnormalities associated with isolated 3-methylcrotonyl-CoA carboxylase deficiency. Metab Brain Dis. 2002 Mar;17(1):13-8. [PubMed:11893004 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Molybdenum cofactor deficiency
  1. van Gennip AH, Abeling NG, Stroomer AE, Overmars H, Bakker HD: The detection of molybdenum cofactor deficiency: clinical symptomatology and urinary metabolite profile. J Inherit Metab Dis. 1994;17(1):142-5. [PubMed:8051926 ]
  2. Zaki MS, Selim L, El-Bassyouni HT, Issa MY, Mahmoud I, Ismail S, Girgis M, Sadek AA, Gleeson JG, Abdel Hamid MS: Molybdenum cofactor and isolated sulphite oxidase deficiencies: Clinical and molecular spectrum among Egyptian patients. Eur J Paediatr Neurol. 2016 Sep;20(5):714-22. doi: 10.1016/j.ejpn.2016.05.011. Epub 2016 May 30. [PubMed:27289259 ]
Sulfite oxidase deficiency, ISOLATED
  1. Zaki MS, Selim L, El-Bassyouni HT, Issa MY, Mahmoud I, Ismail S, Girgis M, Sadek AA, Gleeson JG, Abdel Hamid MS: Molybdenum cofactor and isolated sulphite oxidase deficiencies: Clinical and molecular spectrum among Egyptian patients. Eur J Paediatr Neurol. 2016 Sep;20(5):714-22. doi: 10.1016/j.ejpn.2016.05.011. Epub 2016 May 30. [PubMed:27289259 ]
  2. Rashed MS, Saadallah AA, Rahbeeni Z, Eyaid W, Seidahmed MZ, Al-Shahwan S, Salih MA, Osman ME, Al-Amoudi M, Al-Ahaidib L, Jacob M: Determination of urinary S-sulphocysteine, xanthine and hypoxanthine by liquid chromatography-electrospray tandem mass spectrometry. Biomed Chromatogr. 2005 Apr;19(3):223-30. [PubMed:15558695 ]
Adenosine kinase deficiency
  1. Bjursell MK, Blom HJ, Cayuela JA, Engvall ML, Lesko N, Balasubramaniam S, Brandberg G, Halldin M, Falkenberg M, Jakobs C, Smith D, Struys E, von Dobeln U, Gustafsson CM, Lundeberg J, Wedell A: Adenosine kinase deficiency disrupts the methionine cycle and causes hypermethioninemia, encephalopathy, and abnormal liver function. Am J Hum Genet. 2011 Oct 7;89(4):507-15. doi: 10.1016/j.ajhg.2011.09.004. Epub 2011 Sep 28. [PubMed:21963049 ]
Phosphoribosylpyrophosphate Synthetase Superactivity
  1. Garcia-Pavia P, Torres RJ, Rivero M, Ahmed M, Garcia-Puig J, Becker MA: Phosphoribosylpyrophosphate synthetase overactivity as a cause of uric acid overproduction in a young woman. Arthritis Rheum. 2003 Jul;48(7):2036-41. doi: 10.1002/art.11058. [PubMed:12847698 ]
Associated OMIM IDs
DrugBank IDDB02134
Phenol Explorer Compound IDNot Available
FooDB IDFDB001977
KNApSAcK IDC00019660
Chemspider ID1151
KEGG Compound IDC00385
BioCyc IDXANTHINE
BiGG ID34825
Wikipedia LinkXanthine
METLIN ID82
PubChem Compound1188
PDB IDNot Available
ChEBI ID17712
Food Biomarker OntologyNot Available
VMH IDXAN
MarkerDB IDMDB00000137
Good Scents IDNot Available
References
Synthesis ReferenceProcedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
  3. Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. [PubMed:7677251 ]
  4. Ihara H, Shino Y, Morita Y, Kawaguchi E, Hashizume N, Yoshida M: Is skeletal muscle damaged by the oxidative stress following anaerobic exercise? J Clin Lab Anal. 2001;15(5):239-43. [PubMed:11574951 ]
  5. Niklasson F: Simultaneous liquid-chromatographic determination of hypoxanthine, xanthine, urate, and creatinine in cerebrospinal fluid, with direct injection. Clin Chem. 1983 Aug;29(8):1543-6. [PubMed:6872216 ]
  6. Castro-Gago M, Rodriguez IN, Rodriguez-Nunez A, Guitian JP, Rocamonde SL, Rodriguez-Segade S: Therapeutic criteria in hydrocephalic children. Childs Nerv Syst. 1989 Dec;5(6):361-3. [PubMed:2611770 ]
  7. Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. [PubMed:16324927 ]
  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. Teeuwen HW, Elbers EL, van Rossum JM: Rapid and sensitive gas-chromatographic determination of caffeine in blood plasma, saliva, and xanthine beverages. Mol Biol Rep. 1991 Feb;15(1):1-7. [PubMed:1875916 ]
  10. Becker MA, Kisicki J, Khosravan R, Wu J, Mulford D, Hunt B, MacDonald P, Joseph-Ridge N: Febuxostat (TMX-67), a novel, non-purine, selective inhibitor of xanthine oxidase, is safe and decreases serum urate in healthy volunteers. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1111-6. [PubMed:15571211 ]
  11. Kawasaki N, Tanimoto T, Tanaka A, Hayakawa T, Miyasaka N: Determination of non-protein-bound iron in human synovial fluid by high-performance liquid chromatography with electrochemical detection. J Chromatogr B Biomed Appl. 1994 Jun 17;656(2):436-40. [PubMed:7987499 ]
  12. Cooper N, Khosravan R, Erdmann C, Fiene J, Lee JW: Quantification of uric acid, xanthine and hypoxanthine in human serum by HPLC for pharmacodynamic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jun 6;837(1-2):1-10. Epub 2006 May 2. [PubMed:16631418 ]
  13. Kiss A, Barenyi M, Csontai A: Xanthine stone in the urinary bladder of a male child. Urol Int. 1999;63(4):242-4. [PubMed:10743702 ]
  14. Kjaergaard N, Moller-Petersen JF, Kristiansen FV, Petersen PL, Ekelund S, Skovbo P: Xanthine and hypoxanthine in amniotic fluid during pregnancy. Dan Med Bull. 1990 Dec;37(6):559-60. [PubMed:2127397 ]
  15. Wiley DM, Szabo I, Maguire MH, Finley BE, Bennett TL: Measurement of hypoxanthine and xanthine in late-gestation human amniotic fluid by reversed-phase high-performance liquid chromatography with photodiode-array detection. J Chromatogr. 1990 Nov 30;533:73-86. [PubMed:2081781 ]
  16. Ginsburg I: Could synergistic interactions among reactive oxygen species, proteinases, membrane-perforating enzymes, hydrolases, microbial hemolysins and cytokines be the main cause of tissue damage in infectious and inflammatory conditions? Med Hypotheses. 1998 Oct;51(4):337-46. [PubMed:9824842 ]
  17. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
Hypoxanthine + NAD + Water → Xanthine + NADHdetails
Xanthine + Water + Oxygen → Uric acid + Hydrogen peroxidedetails
Hypoxanthine + NAD + Water → Xanthine + NADH + Hydrogen Iondetails
Hypoxanthine + Oxygen + Water → Xanthine + Hydrogen peroxidedetails
Xanthine + NAD + Water → Uric acid + NADH + Hydrogen Iondetails
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Reactions
Xanthylic acid + Pyrophosphate → Xanthine + Phosphoribosyl pyrophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia (By similarity).
Gene Name:
GDA
Uniprot ID:
Q9Y2T3
Molecular weight:
52836.65
Reactions
Guanine + Water → Xanthine + Ammoniadetails
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
Xanthosine + Phosphate → Xanthine + Ribose 1-phosphatedetails