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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-11-03 18:13:50 UTC
HMDB IDHMDB00157
Secondary Accession NumbersNone
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 is caused by deficiency of the purine salvage enzyme hypoxanthine-guanine phosphoribosyltransferase. (OMIN 308000).
Structure
Thumb
Synonyms
  1. 1,7-Dihydro-6H-purin-6-one
  2. 1,7-Dihydro-6H-purine-6-one
  3. 1H,7H-Hypoxanthine
  4. 3H-Purin-6-ol
  5. 4-Hydroxy-1H-purine
  6. 6(1H)-Purinone
  7. 6-Hydroxy-1H-purine
  8. 6-Hydroxypurine
  9. 6-Oxopurine
  10. 7H-Purin-6-ol
  11. 9H-Purin-6(1H)-one
  12. 9H-Purin-6-ol
  13. Hypoxanthine enol
  14. Purin-6(1H)-one
  15. Purin-6(3H)-one
  16. Purin-6-ol
  17. Purine-6-ol
  18. Sarcine
  19. Sarkin
  20. Sarkine
Chemical FormulaC5H4N4O
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
IUPAC Name7H-purin-6-ol
Traditional Name7H-purin-6-ol
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazopyrimidines
Sub ClassPurines and Purine Derivatives
Other Descriptors
  • Organic Compounds
  • Purine alkaloids(KEGG)
  • a purine base(Cyc)
  • a purine-related compound(Cyc)
  • oxopurine(ChEBI)
  • purine nucleobase(ChEBI)
Substituents
  • Imidazole
  • Pyrimidine
Direct ParentHypoxanthines
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Peroxisome
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 Solubility13.0ALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.5 m3·mol-1ChemAxon
Polarizability11.82 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Peroxisome
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.086 +/- 0.044 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified11.02 +/- 3.67 uMAdult (>18 years old)BothNormal 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 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)Not SpecifiedNormal 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 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
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 QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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
    • Dame, ZT. et al. ...
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 Quantified7.2 (1.8-24.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.7 +/- 0.4 uMAdult (>18 years old)BothLesch-Nyhan syndrome details
BloodDetected and Quantified52.3 uMAdult (>18 years old)Not SpecifiedHeart 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 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 Quantified2.50 (2.00-3.00) uMAdult (>18 years old)BothDegenerative disc disease details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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 Quantified6.8 +/- 4.8 umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
Associated Disorders and Diseases
Disease References
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
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
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
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. 2008 Oct 25. Pubmed: 18953024
Associated OMIM IDs
DrugBank IDDB04076
DrugBank Metabolite IDDBMET00493
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003949
KNApSAcK IDNot Available
Chemspider ID768
KEGG Compound IDC00262
BioCyc IDHYPOXANTHINE
BiGG ID34434
Wikipedia LinkHypoxanthine
NuGOwiki LinkHMDB00157
Metagene LinkHMDB00157
METLIN ID83
PubChem Compound790
PDB IDHPA
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. 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(1):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