Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2022-01-23 17:28:30 UTC |
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NP-MRD ID | NP0000434 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Hypoxanthine |
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Description | Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as purines. Purines are a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Hypoxanthine is also classified as an oxopurine, 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 nucleotide salvage pathway. Hypoxanthine exists in all living species, ranging from bacteria to plants to humans. Hypoxanthine has been detected, but not quantified in, several different foods, such as radish (var.), Mountain yams, welsh onions, greenthread tea, and common beets. Hypoxanthine is occasionally found as a constituent of nucleic acids, where it is present in the anticodon of tRNA in the form of its nucleoside inosine. Biologically, hypoxanthine can be formed a number of ways. For instance, it is one of the products of the action of xanthine oxidase on xanthine. However, more frequently xanthine is formed from oxidation of hypoxanthine by xanthine oxidoreductase. The enzyme hypoxanthine-guanine phosphoribosyltransferase converts hypoxanthine into IMP in the nucleotide salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. Under normal circumstances hypoxanthine is readily converted to uric acid. In this process, hypoxanthine is first oxidized to xanthine, which is further oxidized to uric acid by xanthine oxidase. Molecular oxygen, the oxidant in both reactions, is reduced to H2O2 and other reactive oxygen species. In humans, uric acid is the final product of purine degradation and is excreted in the urine. Within humans, hypoxanthine participates in a number of other enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine through its interaction with the enzyme purine nucleoside phosphorylase. Hypoxanthine is also involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency. Purine nucleoside phosphorylase (PNP) deficiency is a disorder of the immune system (primary immunodeficiency) characterized by recurrent infections, neurologic symptoms, and autoimmune disorders. PNP deficiency causes a shortage of white blood cells, called T-cells, that help fight infection. Affected individuals develop neurologic symptoms, such as stiff or rigid muscles (spasticity), uncoordinated movements (ataxia), developmental delay, and intellectual disability. PNP deficiency is associated with an increased risk to develop autoimmune disorders, such as autoimmune hemolytic anemia, idiopathic thrombocytopenic purpura (ITP), autoimmune neutropenia, thyroiditis, and lupus. |
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Structure | InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) |
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Synonyms | Value | Source |
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6(1H)-Purinone | ChEBI | 6-Oxopurine | ChEBI | 9H-Purin-6(1H)-one | ChEBI | Hyp | ChEBI | Purin-6(1H)-one | ChEBI | Purine-6-ol | ChEBI | 1,7-Dihydro-6H-purin-6-one | HMDB | 1,7-Dihydro-6H-purine-6-one | HMDB | 1H,7H-Hypoxanthine | HMDB | 3H-Purin-6-ol | HMDB | 4-Hydroxy-1H-purine | HMDB | 6-Hydroxy-1H-purine | HMDB | 6-Hydroxypurine | HMDB | 7H-Purin-6-ol | HMDB | 9H-Purin-6-ol | HMDB | Hypoxanthine enol | HMDB | Purin-6(3H)-one | HMDB | Purin-6-ol | HMDB | Sarcine | HMDB | Sarkin | HMDB | Sarkine | HMDB |
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Chemical Formula | C5H4N4O |
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Average Mass | 136.1115 Da |
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Monoisotopic Mass | 136.03851 Da |
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IUPAC Name | 7H-purin-6-ol |
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Traditional Name | 6-hydroxypurine |
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CAS Registry Number | 68-94-0 |
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SMILES | OC1=NC=NC2=C1NC=N2 |
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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) |
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InChI Key | FDGQSTZJBFJUBT-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | Hypoxanthines |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 150 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.7 mg/mL | Yalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189. | LogP | -1.11 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Pietz J, Guttenberg N, Gluck L: Hypoxanthine: a marker for asphyxia. Obstet Gynecol. 1988 Nov;72(5):762-6. [PubMed:3140152 ]
- Saari H: Oxygen derived free radicals and synovial fluid hyaluronate. Ann Rheum Dis. 1991 Jun;50(6):389-92. [PubMed:1711835 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Dogan HO, Senol O, Bolat S, Yildiz SN, Buyuktuna SA, Sariismailoglu R, Dogan K, Hasbek M, Hekim SN: Understanding the pathophysiological changes via untargeted metabolomics in COVID-19 patients. J Med Virol. 2021 Apr;93(4):2340-2349. doi: 10.1002/jmv.26716. Epub 2020 Dec 17. [PubMed:33300133 ]
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