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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-04-01 19:18:30 UTC
HMDB IDHMDB0000157
Secondary Accession Numbers
  • HMDB00157
Metabolite Identification
Common NameHypoxanthine
DescriptionHypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. Lesch-Nyhan disease, an inborn error of metabolism, is caused by deficiency of the purine salvage enzyme hypoxanthine-guanine phosphoribosyltransferase (OMIN 308000). Hypoxanthine is also found to be associated with xanthinuria type 1, which is an inborn error of metabolism.
Structure
Data?1547234046
Synonyms
ValueSource
6(1H)-PurinoneChEBI
6-OxopurineChEBI
9H-Purin-6(1H)-oneChEBI
HypChEBI
Purin-6(1H)-oneChEBI
Purine-6-olChEBI
1,7-Dihydro-6H-purin-6-oneHMDB
1,7-Dihydro-6H-purine-6-oneHMDB
1H,7H-HypoxanthineHMDB
3H-Purin-6-olHMDB
4-Hydroxy-1H-purineHMDB
6-Hydroxy-1H-purineHMDB
6-HydroxypurineHMDB
7H-Purin-6-olHMDB
9H-Purin-6-olHMDB
Hypoxanthine enolHMDB
Purin-6(3H)-oneHMDB
Purin-6-olHMDB
SarcineHMDB
SarkinHMDB
SarkineHMDB
Chemical FormulaC5H4N4O
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
IUPAC Name7H-purin-6-ol
Traditional Name6-hydroxypurine
CAS Registry Number68-94-0
SMILES
OC1=NC=NC2=C1NC=N2
InChI Identifier
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyFDGQSTZJBFJUBT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-1.11HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP-0.55ALOGPS
logP-0.048ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)2.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.5 m³·mol⁻¹ChemAxon
Polarizability11.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0159-3970000000-0d844fae4a1ffe158823JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1790000000-ae93bf8bf07b30b65e1aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9340000000-1184c503fb61344c4853JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3590000000-a419976950afe7934cbcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9800000000-9c266d6963658e9d2cf1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-3970000000-0d844fae4a1ffe158823JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1790000000-ae93bf8bf07b30b65e1aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9340000000-1184c503fb61344c4853JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3590000000-a419976950afe7934cbcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2890000000-3be4d08be45781881bc1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1590000000-bb6f003bfa7bd04628a1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-8900000000-e20eb5d939a2c406a6e2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0613-5900000000-be0624b928ba71cc797dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2b36c20acd9973b317f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0api-9800000000-fb4e3cccb7d27d119febJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aor-9200000000-33c2f9eedf9a878530beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000i-9800000000-9c266d6963658e9d2cf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-4da64abddc3ac8ab573aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-859f61101b12be0b2978JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-f5d899e7988568d5bcabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-e19e6d04568d3560eb4aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-8def0d2ec82152826763JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-2900000000-a8361951a2f702a217c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-3f653a7c81b328e46cb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0080290000-be98ce43421dbf9007faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0930030000-56ea204dcb077bc174c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-4c2d1980f9e5e4b720a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-26b3c93bc9dea5a88032JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c367cd4c23aea0f74ecbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000l-8900000000-91e35cdcc11d357119f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-4fb8f4ee2d35aa874617JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-9000000000-7934b3037f39d69fc40aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-ad93e267446292bf247bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-9000000000-4b8f9e13ed7adf0888c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-9000000000-f295755f591e27bb9f07JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-aee48a44f42a4b767844JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-f5ebd92e86cf00f28cf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-9a1ad1aa2d8fb621b608JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-ebf57ea530a2d4e31ffaJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Peroxisome
Biospecimen Locations
  • Amniotic Fluid
  • Blood
  • Breast Milk
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.086 +/- 0.044 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.300 +/- 1.100 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified11.02 +/- 3.67 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.7 +/- 0.4 uMAdult (>18 years old)Male
normal
details
BloodDetected and Quantified2.2 +/- 1.1 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified8.14 +/- 2.86 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified4.22 +/- 1.61 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.66 +/- 0.38 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified5.6 (3.1-7.1) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.0 +/-0.9 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.87 +/- 0.36 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.0 +/- 0.9 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified5.6 (3.1-7.1) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.38 +/- 0.18 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified34.2 +/- 10.3 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified2.3 +/- 1.5 uMAdult (>18 years old)Female
Normal
details
Cellular CytoplasmDetected and Quantified2 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.94 (5.20-6.68) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.6+/-0.6 uMChildren (1 - 13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.6 (1.8-5.5) uMNewborn (0-30 days old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.4 (0.6-4.1) uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.8 (0.6-5.1) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified1242 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified1540 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified1363 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified3.72 +/- 2.50 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified5.83 +/- 5.65 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected and Quantified1.55 +/- 0.973 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.57 +/- 1.14 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified2.12 +/- 1.17 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.91 +/- 0.37 uMAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified2.15 +/- 0.34 uMAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified1.11 +/- 0.20 uMAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified28.15 +/- 11.95 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified6.63 +/- 6.938 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.957 +/- 1.470 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified4.67 (2.8-6.38) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified4-60 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified7.2 (1.8-24.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified0-25 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified17.1 +/- 1.0 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified5.314 +/- 1.583 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified7.2 +/- 3.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.78 +/- 3.99 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified4.82 +/- 2.20 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified2.30 +/- 2.48 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.7 +/- 0.4 uMAdult (>18 years old)BothLesch-Nyhan syndrome details
BloodDetected and Quantified3.1 uMAdult (>18 years old)FemalePhosphoribosylpyrophosphate Synthetase Superactivity details
BloodDetected and Quantified52.3 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified18.88 +/- 8.30 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified5.56 +/- 1.74 uMAdult (>18 years old)BothCanavan disease details
BloodDetected and Quantified1.6 uMChildren (1-13 years old)Male
Xanthinuria type 1
details
BloodDetected and Quantified3.6 uMAdult (>18 years old)Female
Xanthinuria type 1
details
BloodDetected and Quantified0-31 uMChildren (1-13 years old)BothXanthinuria type 1 details
BloodDetected and Quantified7.0 +/- 3.2 uMAdult (>18 years old)Male
Lesch-Nyhan syndrome
details
BloodDetected and Quantified4.8 +/- 1.0 uMAdult (>18 years old)BothSolid tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified5.71 (3.99-7.43) uMAdult (>18 years old)Both
Hydrocephalus
details
Cerebrospinal Fluid (CSF)Detected and Quantified9.91 (8.01-11.8) uMAdult (>18 years old)Both
Hydrocephalus
details
Cerebrospinal Fluid (CSF)Detected and Quantified5.2 uMChildren (1 - 13 years old)Not SpecifiedIsolated 3-Methylcrotonyl-CoA Carboxylase Deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified2.50 (2.00-3.00) uMAdult (>18 years old)BothDegenerative disc disease details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not Quantified Adult (>18 years old)Femalerheumatoid arthritis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not Quantified Adult (>18 years old)BothOral cancer details
SalivaDetected but not Quantified Adult (>18 years old)FemaleBreast cancer details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPeriodontal diseases details
SalivaDetected and Quantified2.60 +/- 1.07 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified2.99 +/- 1.49 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified3.53 +/- 3.84 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified9.434 +/- 6.582 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified16.846 umol/mmol creatinineAdult (>18 years old)FemalePhosphoribosylpyrophosphate Synthetase Superactivity details
UrineDetected and Quantified6.8 +/- 4.8 umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified46 umol/mmol creatinineChildren (1-13 years old)Not Specified
Molybdenum cofactor deficiency
details
UrineDetected and Quantified65 umol/mmol creatinineAdult (>18 years old)Male
Xanthinuria type 1
details
UrineDetected and Quantified74.846 umol/mmol creatinineAdult (>18 years old)Male
Lesch-Nyhan syndrome
details
UrineDetected and Quantified88 umol/mmol creatinineNewborn (0-30 days old)Not Specified
Molybdenum cofactor deficiency
details
UrineDetected and Quantified4.3-53.0 umol/mmol creatinineChildren (1-13 years old)BothSulfite oxidase deficiency details
UrineDetected and Quantified61.8-138.0 umol/mmol creatinineChildren (1-13 years old)BothXanthinuria type 1 details
UrineDetected but not Quantified Adult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified15.12 +/- 17.44 umol/mmol creatinineAdult (>18 years old)BothCanavan disease details
UrineDetected but not Quantified Adult (>18 years old)Male
Hepatocellular carcinoma
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. 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 ]
Thymidine treatment
  1. Leyva A, Schornagel JH, Kraal I, Wadman SK, Pinedo HM: Clinical and biochemical studies of high-dose thymidine treatment in patients with solid tumors. J Cancer Res Clin Oncol. 1984;107(3):211-6. [PubMed:6736109 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
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 ]
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 ]
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
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 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Hepatocellular carcinoma
  1. Wu H, Xue R, Dong L, Liu T, Deng C, Zeng H, Shen X: Metabolomic profiling of human urine in hepatocellular carcinoma patients using gas chromatography/mass spectrometry. Anal Chim Acta. 2009 Aug 19;648(1):98-104. doi: 10.1016/j.aca.2009.06.033. Epub 2009 Jun 21. [PubMed:19616694 ]
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 ]
Sulfite oxidase deficiency, ISOLATED
  1. 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 ]
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 IDDB04076
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003949
KNApSAcK IDC00001502
Chemspider ID768
KEGG Compound IDC00262
BioCyc IDHYPOXANTHINE
BiGG ID34434
Wikipedia LinkHypoxanthine
METLIN ID83
PubChem Compound790
PDB IDNot Available
ChEBI ID17368
References
Synthesis Reference Shaw, Elliott.New synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. Journal of Biological Chemistry (1950), 185 439-47.
Material Safety Data Sheet (MSDS)Not Available
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. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  4. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  5. Bullo B, Marlewski M, Smolenski RT, Rutkowski B, Swierczynski J, Manitius J: Erythrocyte nucleotides and blood hypoxanthine in patients with uremia evaluated immediately and 24 hours after hemodialysis. Ren Fail. 1996 Mar;18(2):247-52. [PubMed:8723362 ]
  6. 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 ]
  7. Inokuchi T, Moriwaki Y, Takahashi S, Tsutsumi Z, Ka T, Yamamoto A, Cheng J, Hashimoto-Tamaoki T, Hada T, Yamamoto T: Identification of a new point mutation in hypoxanthine phosphoribosyl transferase responsible for hyperuricemia in a female patient. Metabolism. 2004 Nov;53(11):1500-2. [PubMed:15536609 ]
  8. 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 ]
  9. Pietz J, Guttenberg N, Gluck L: Hypoxanthine: a marker for asphyxia. Obstet Gynecol. 1988 Nov;72(5):762-6. [PubMed:3140152 ]
  10. Saari H: Oxygen derived free radicals and synovial fluid hyaluronate. Ann Rheum Dis. 1991 Jun;50(6):389-92. [PubMed:1711835 ]
  11. 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 ]
  12. Storm H, Rognum TO, Saugstad OD, Skullerud K, Reichelt KL: Beta-endorphin immunoreactivity in spinal fluid and hypoxanthine in vitreous humour related to brain stem gliosis in sudden infant death victims. Eur J Pediatr. 1994 Sep;153(9):675-81. [PubMed:7957429 ]
  13. Koellner G, Luic M, Shugar D, Saenger W, Bzowska A: Crystal structure of calf spleen purine nucleoside phosphorylase in a complex with hypoxanthine at 2.15 A resolution. J Mol Biol. 1997 Jan 17;265(2):202-16. [PubMed:9020983 ]
  14. 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 ]
  15. Smolenska Z, Kaznowska Z, Zarowny D, Simmonds HA, Smolenski RT: Effect of methotrexate on blood purine and pyrimidine levels in patients with rheumatoid arthritis. Rheumatology (Oxford). 1999 Oct;38(10):997-1002. [PubMed:10534552 ]
  16. Saiki S, Sato T, Kohzuki M, Kamimoto M, Yosida T: Changes in serum hypoxanthine levels by exercise in obese subjects. Metabolism. 2001 Jun;50(6):627-30. [PubMed:11398135 ]
  17. 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 ]
  18. Saiki S, Sato T, Hiwatari M, Harada T, Oouchi M, Kamimoto M: Relation between changes in serum hypoxanthine levels by exercise and daily physical activity in the elderly. Tohoku J Exp Med. 1999 May;188(1):71-4. [PubMed:10494902 ]

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
Hypoxanthine + NAD + Water → Xanthine + NADH + Hydrogen Iondetails
Hypoxanthine + Oxygen + Water → Xanthine + Hydrogen peroxidedetails
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
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Molecular weight:
50112.3
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
Inosine + Phosphoric acid → Hypoxanthine + Ribose 1-phosphatedetails
Deoxyinosine + Phosphoric acid → Hypoxanthine + Deoxyribose 1-phosphatedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]