Grundinformationen
- CAS
68-94-0- Standard-SMILES
O=c1[nH]cnc2nc[nH]c12- InChIKey
FDGQSTZJBFJUBT-UHFFFAOYSA-N- Summenformel
- C5H4N4O
- Durchschnittliche Molmasse
- 136,11 g/mol
Überblick
Hypoxanthine is a purine nucleobase that consists of purine bearing an oxo substituent at position 6. It has a role as a fundamental metabolite. It is an oxopurine, a purine nucleobase and a nucleobase analogue. It is functionally related to an adenine.
Namen und Bezeichner
- Bevorzugter Name
- Hypoxanthine
- IUPAC
- 1,7-dihydropurin-6-one
- Lokaler Name
- Purin-6(1H)-on
- Englischer Name
- 6-Hydroxypurine
- Summenformel
- C5H4N4O
- Molmasse
- 136.11
Namen und Synonyme
hypoxanthine68-94-06-Hydroxypurine9H-Purin-6-ol7H-Purin-6-olSarkin3H-Purin-6-olSarcine1,7-Dihydro-6H-purin-6-one6-OxopurineSarkineHypoxanthine enol
Weitere Namen anzeigen
Hypoxanthine,99%Hypoxanthine-d4Hypoxanthine, 99.5%3,7-dihydropurin-6-oneAzathioprine EP Impurity F6H-Purin-6-one, 1,9-dihydro-
Purin-6(1H)-one6-Hydroxy-1H-purinePurin-6-ol9H-Purin-6(1H)-one6(1H)-PurinonePurin-6(3H)-one6H-Purin-6-one, 1,7-dihydro-Purine-6-ol
Datenbank-Bezeichner
- CAS
68-94-0- PubChem CID
- 135398638
- ChEMBL
CHEMBL1427- ChEBI
CHEBI:17368- UNII
- 2TN51YD919
- EC Number
- 200-697-3
- Nikkaji
- J1.934H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 70,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 190
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP
-1.11
-0.96
Solubility0.7 mg/mL
Melting Point150 °C
Physical Description
Solid; [Merck Index] White powder; [Alfa Aesar MSDS]
Solid
Ionization Efficiency
Positive
2.18
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section
123.66 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 60% (6 of 10) of all reports.
Warning
H315 (40%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 6H-Purin-6-one, 1,7-dihydro-
6H-Purin-6-one, 1,9-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 6H-Purin-6-one, 1,9-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 22-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/25540
6H-Purin-6-one, 1,7-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryTeratogenic in mice at 1,000 mg/kg but not rats at 700 mg/kg; [REPROTOX] May cause irritation; Risk of impaired fertility and harm to the unborn child; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (40%)
Toxikologische Informationen
Treatment
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Under normal circumstances hypoxanthine is readily converted to uric acid. The enzyme xanthine oxidase makes uric acid from xanthine and hypoxanthine, which in turn are produced from other purines. In humans and higher primates, uric acid is the final oxidation (breakdown) product of purine metabolism and is excreted in urine.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Verwendung und Herstellung
Uses
A breakdown product of nucleic acids; [Merck Index]
Naturally produced by the body (endogenous).
U.S. Production2023: <50,000 lb
General Manufacturing Information6H-Purin-6-one, 1,9-dihydro-: ACTIVE
Anwendungen
BeschreibungHypoxanthine is a naturally occurring purine derivative and intermediate in the synthesis of uric acid. It is elevated in the spinal fluid of patients with Lesch-Nyhan syndrome, a metabolic disorder whose symptoms include cerebral palsy, cognitive deficits, motor dysfunction, self-mutilation, and hyperuricemia. Injection of hypoxanthine (10 μM) increases succinate dehydrogenase and complex II activities and decreases cytochrome c oxidase activity, resulting in neuroenergetic impairment, ATP depletion, and cellular apoptosis in rat striatum. It is also used to induce hyperuricemia in mice for use in the development of hypouricemic agents.
Zugehörige Reaktionen
23
Notizen zur Verbindung
Wird geladen…