Human Metabolome Database Version 3.5

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 | PDB | 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
  • Drug metabolite
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • Waste products
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
  • Kidney
  • Liver
  • 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 Reference
Amniotic Fluid Detected and Quantified
0.086 +/- 0.044 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
8.14 +/- 2.86 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
4.22 +/- 1.61 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
1.66 +/- 0.38 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
4.87 +/- 0.36 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
1.0 +/- 0.9 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
5.6 (3.1-7.1) uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
0.38 +/- 0.18 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
34.2 +/- 10.3 uM Adult (>18 years old) Not Specified Normal
Cellular Cytoplasm Detected and Quantified
2 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
5.94 (5.20-6.68) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
3.6 (1.8-5.5) uM Newborn (0-30 days old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.4 (0.6-4.1) uM Children (1-13 year old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
1.8 (0.6-5.1) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
4.67 (2.8-6.38) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
7.2 (1.8-24.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
5.78 +/- 3.99 umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
4.82 +/- 2.20 umol/mmol creatinine Adolescent (13-18 years old) Both Normal
Urine Detected and Quantified
2.30 +/- 2.48 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 5.7 +/- 0.4 uM Adult (>18 years old) Both Lesch-Nyhan syndrome
Blood Detected and Quantified 52.3 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 5.56 +/- 1.74 uM Adult (>18 years old) Both Canavan disease
Blood Detected and Quantified 4.8 +/- 1.0 uM Adult (>18 years old) Both Solid tumors
Cerebrospinal Fluid (CSF) Detected and Quantified 5.71 (3.99-7.43) uM Adult (>18 years old) Both Comment Hydrocephalus
Cerebrospinal Fluid (CSF) Detected and Quantified 9.91 (8.01-11.8) uM Adult (>18 years old) Both Comment Hydrocephalus
Cerebrospinal Fluid (CSF) Detected and Quantified 2.50 (2.00-3.00) uM Adult (>18 years old) Both Degenerative disc disease
Urine Detected and Quantified 6.8 +/- 4.8 umol/mmol creatinine Not Specified Both Lung cancer
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Autosomal dominant polycystic kidney disease
Urine Detected and Quantified 15.12 +/- 17.44 umol/mmol creatinine Adult (>18 years old) Both Canavan disease
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
      • 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 Link_out
          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
                      DrugBank Metabolite ID DBMET00493 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:
                      Hypoxanthine + NAD + Water unknown Xanthine + NADH details
                      Hypoxanthine + NAD + Water unknown Xanthine + NADH + Hydrogen Ion details
                      Hypoxanthine + Oxygen + Water unknown Xanthine + Hydrogen peroxide details
                      Gene Name: XDH
                      Uniprot ID: P47989 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Hypoxanthine-guanine phosphoribosyltransferase
                      Reactions:
                      Inosinic acid + Pyrophosphate unknown Hypoxanthine + Phosphoribosyl pyrophosphate details
                      Gene Name: HPRT1
                      Uniprot ID: P00492 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Equilibrative nucleoside transporter 2
                      Reactions: Not Available
                      Gene Name: SLC29A2
                      Uniprot ID: Q14542 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Purine nucleoside phosphorylase
                      Reactions:
                      Inosine + Phosphoric acid unknown Hypoxanthine + Ribose 1-phosphate details
                      Deoxyinosine + Phosphoric acid unknown Hypoxanthine + Deoxyribose 1-phosphate details
                      Gene Name: PNP
                      Uniprot ID: P00491 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA