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Human Metabolome Database Version 3.5

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Showing metabocard for Hypoxanthine (HMDB00157)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:59 -0700
HMDB ID HMDB00157
Secondary Accession Numbers None
Metabolite Identification
Common Name Hypoxanthine
Description Hypoxanthine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C5H4N4O
Average Molecular Weight 136.1115
Monoisotopic Molecular Weight 136.03851077
IUPAC Name 7H-purin-6-ol
Traditional IUPAC Name 7H-purin-6-ol
CAS Registry Number 68-94-0
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 Key FDGQSTZJBFJUBT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class Purines 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 Parent Hypoxanthines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 150 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.7 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP -1.11 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 13 g/L ALOGPS
LogP -0.55 ALOGPS
LogP -0.048 ChemAxon
LogS -1.02 ALOGPS
pKa (strongest acidic) 8.72 ChemAxon
pKa (strongest basic) 2.66 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.69 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 35.5 ChemAxon
Polarizability 11.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Peroxisome
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Intestine
  • Placenta
  • Testes
  • Erythrocyte
  • Epidermis
  • Prostate
  • Adipose Tissue
  • Platelet
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Amniotic Fluid Detected and Quantified
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0.086 +/- 0.044 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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8.14 +/- 2.86 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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4.22 +/- 1.61 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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1.66 +/- 0.38 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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4.87 +/- 0.36 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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1.0 +/- 0.9 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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5.6 (3.1-7.1) uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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0.38 +/- 0.18 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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34.2 +/- 10.3 uM Adult (>18 years old) Not Specified Normal Not Available
Cellular Cytoplasm Detected and Quantified
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2 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5.94 (5.20-6.68) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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3.6 (1.8-5.5) uM Newborn (0-30 days old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.4 (0.6-4.1) uM Children (1-13 year old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.8 (0.6-5.1) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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4.67 (2.8-6.38) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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7.2 (1.8-24.1) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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5.78 +/- 3.99 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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4.82 +/- 2.20 umol/mmol creatinine Adolescent (13-18 years old) Both Normal Not Available
Urine Detected and Quantified
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2.30 +/- 2.48 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
5.7 +/- 0.4 uM Adult (>18 years old) Both Lesch-Nyhan syndrome Not Available
Blood Detected and Quantified
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52.3 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
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5.56 +/- 1.74 uM Adult (>18 years old) Both Canavan disease Not Available
Blood Detected and Quantified
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4.8 +/- 1.0 uM Adult (>18 years old) Both Solid tumors Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5.71 (3.99-7.43) uM Adult (>18 years old) Both Hydrocephalus Self-compensated hydrocephalics
Cerebrospinal Fluid (CSF) Detected and Quantified
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9.91 (8.01-11.8) uM Adult (>18 years old) Both Hydrocephalus Non-compensated hydrocephalics (pre-shunt...
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.50 (2.00-3.00) uM Adult (>18 years old) Both Degenerative disc disease Not Available
Urine Detected and Quantified
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6.8 +/- 4.8 umol/mmol creatinine Not Specified Both Lung cancer Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Autosomal dominant polycystic kidney disease Not Available
Urine Detected and Quantified
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15.12 +/- 17.44 umol/mmol creatinine Adult (>18 years old) Both Canavan disease Not Available
Associated Disorders and Diseases
Disease References
Degenerative disc disease
  • 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 Link_out
    Lung Cancer
      • HMP experimental
      Hydrocephalus
      • 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 Link_out
        Lesch-Nyhan syndrome
        • 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 Link_out
          Canavan disease
          • 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 Link_out
            Associated OMIM IDs
            DrugBank ID DB04076 Link_out
            Phenol Explorer Compound ID Not Available
            Phenol Explorer Metabolite ID Not Available
            FoodDB ID FDB003949
            KNApSAcK ID Not Available
            Chemspider ID 768 Link_out
            KEGG Compound ID C00262 Link_out
            BioCyc ID HYPOXANTHINE Link_out
            BiGG ID 34434 Link_out
            Wikipedia Link Hypoxanthine Link_out
            NuGOwiki Link HMDB00157 Link_out
            Metagene Link HMDB00157 Link_out
            METLIN ID 83 Link_out
            PubChem Compound 790 Link_out
            PDB ID HPA Link_out
            ChEBI ID 17368 Link_out
            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. 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 Link_out
            2. 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 Link_out
            3. 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 Link_out
            4. 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 Link_out
            5. Pietz J, Guttenberg N, Gluck L: Hypoxanthine: a marker for asphyxia. Obstet Gynecol. 1988 Nov;72(5):762-6. Pubmed: 3140152 Link_out
            6. Saari H: Oxygen derived free radicals and synovial fluid hyaluronate. Ann Rheum Dis. 1991 Jun;50(6):389-92. Pubmed: 1711835 Link_out
            7. 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 Link_out
            8. 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 Link_out
            9. 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 Link_out
            10. 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 Link_out
            11. 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 Link_out
            12. 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 Link_out
            13. 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 Link_out
            14. 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 Link_out
            15. 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 Link_out
            16. 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 Link_out
            17. 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 Link_out
            18. 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 Link_out
            Enzymes
            Name: Xanthine dehydrogenase/oxidase
            Reactions:
            • xanthine + H2O + O2 = urate + H2O2 [RN:R02107]
            Gene Name: XDH
            Uniprot ID: P47989 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Hypoxanthine-guanine phosphoribosyltransferase
            Reactions:
            • IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01132]
            Gene Name: HPRT1
            Uniprot ID: P00492 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Equilibrative nucleoside transporter 2
            Reactions:
              Gene Name: SLC29A2
              Uniprot ID: Q14542 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Purine nucleoside phosphorylase
              Reactions:
              • purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate [RN:R08368]
              Gene Name: PNP
              Uniprot ID: P00491 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA