Grundinformationen
- Standard-SMILES
O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1- InChIKey
LEHOTFFKMJEONL-UHFFFAOYSA-N- Summenformel
- C5H4N4O3
- Durchschnittliche Molmasse
- 168,11 g/mol
- Monoisotopische Masse
- 168,02833999
Überblick
7,9-dihydro-1H-purine-2,6,8(3H)-trione is an oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a tautomer of a 2,6-dihydroxy-7,9-dihydro-8H-purin-8-one, a 9H-purine-2,6,8-triol, a 7H-purine-2,6,8-triol, a 1H-purine-2,6,8-triol and a 5,7-dihydro-1H-purine-2,6,8(9H)-trione.
Namen und Bezeichner
- Bevorzugter Name
- Uric Acid
- IUPAC
- 7,9-dihydro-3H-purine-2,6,8-trione
- Lokaler Name
- Harnsure
- Englischer Name
- Uric acid
- Summenformel
- C5H4N4O3
- Molmasse
- 168.11
Namen und Synonyme
uric acid69-93-2urateLithic acid2,6,8-trioxypurine2,6,8-trihydroxypurine7,9-Dihydro-1H-purine-2,6,8(3H)-trione2,6,8-Trioxopurine1H-Purine-2,6,8-triol1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-Purine-2,6,8(1H,3H,9H)-trione7,9-dihydro-3H-purine-2,6,8-trione
Weitere Namen anzeigen
TRIKETOPURINEUric aciNSC 3975URIC OXIDEUricAcidGrURIC ACID(RG)
2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneUricum acidumIdelalisib metabolite m54trioxopurineDTXSID3042508NSC-3975268B43MJ25DTXCID1022508
Datenbank-Bezeichner
- CAS
69-93-2- PubChem CID
- 1175
- DTXSID
DTXSID3042508- ChEMBL
CHEMBL792- ChEBI
CHEBI:17775- UNII
- 268B43MJ25
- EC Number
- 200-720-7
- Nikkaji
- J2.372H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,9
- Polarare Oberfläche (TPSA)
- 99,3 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 332
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning; Buffering
SpringerMaterials PropertiesCrystal structure
LogP-2.17
Solubility0.06 mg/mL
Melting Point
Greater than 300 °C
> 300 °C
Physical Description
White odorless solid; [Merck Index] Beige powder; [Sigma-Aldrich MSDS]
Solid
Dissociation Constants5.4
Collision Cross Section
126.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3042508]
126.93 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
127.08 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
125.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
142.6 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 °C · >300 °C (lit.)
- Siedepunkt
- 297.02 °C · 297.02°C (rough estimate)
- Dichte
- 1 · 1,9 g/cm3
- Brechungsindex
- 1.99 · 1.9900 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- Aqueous Base (Sparingly, Heated)
- pka
- 3.89 · 3.89(at 12℃)
- Aggregatzustand
- crystalline
- Farbe
- White to off-white
- Geruch (Odor)
- Odorless
- Biologische Quelle
- animal (seabird feces (guano))
- Wasserlöslichkeit
- 1 M · Soluble in 1M sodium hydroxide solution. Slightly soluble in water. Insoluble in ether and alcohol.
- Spezifische Wärmekapazität
- 0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
- Merck
- 14 · 14,9875
- BRN
- 156158 · 156158
- Stabilität
- Stable. Incompatible with acids, bases, oxidising agents.
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONINGBUFFERING
- InChI
- 1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
- InChIKey
- LEHOTFFKMJEONL-UHFFFAOYSA-N
- SMILES
- O=C1NC(=O)C2=C(N1)NC(=O)N2
- LogP
- -1.73 · -1.730 (est)
- CAS Datenbank
- 69 · 69-93-2(CAS DataBase Reference)
- EPA chemische Informationen
- Uric acid (69-93-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 96.8% (30 of 31) of all reports.
Not Classified
Aggregated GHS information provided per 31 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: 1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-
Status: Active Update: 12-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23478
1H-Purine-2,6,8(3H)-trione, 7,9-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 SummaryMay cause irritation; Reproductive effects observed in rats; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339900
- RTECS-Nr.
- YU7050080
- risk_code
- 33-36/37/38
- Toxizität
- A nitrogenous end product and the principal excretory product of purine metabolism in mammals. In birds and reptiles, it is the principal end product of nitrogen metabolism in general. Defects in uric acid metabolism and excretion appear to be associated with a number of disease states, and it frequently occurs as a component of renal calculi. It has not been associated closely with toxic insults except in the case of lead poisoning. Lead causes an elevation in blood uric acid concentration (uric acidemia) and a decrease in uric acid excretion.
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Uric acid is a strong reducing agent (donates electrons) and an antioxidant. Normally in humans, one of the main antioxidants in plasma is uric acid. Several animal studies have found that animals given exogenous uric acid within 3 hours after a stroke had decreased infarct volume, improved neurologic function, and diminished inflammatory responses providing evidence for the neuroprotective effects of uric acid. In some early human studies, uric acid has so far shown similar neuroprotective effects, in both the cortex and subcortex areas, due to its antioxidant effects such as decreased lipid peroxidation, and there appears to be no significant toxicities.
Mechanism of ActionThe exact mechanism of action for uric acid's antioxidant effects have not yet been elucidated.
Metabolism/MetabolitesIn higher primates and humans, the enzyme, uricase, is absent, and thus uric acid is not further metabolized and is excreted. In all other mammals, uric acid is metabolized by uricase to allantoin, which is then excreted.
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Absorption, Distribution and ExcretionUric acid is eliminated by the kidneys.
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Verwendung und Herstellung
UsesFound in the urine of all carnivores; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Use ClassificationCosmetics -> Skin conditioning; Buffering
General Manufacturing Information1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-: ACTIVE
Anwendungen
OccurrenceUric acid is found in the urine, blood, and muscle juices of carnivorous animals (herbivorous animals secrete hippuric acid), in the excrement of birds, serpents and insects, and is an oxidation product of the complex nitrogenous compounds of the animal organism.
VerwendenUric Acid is a heterocyclcic compound that is created when purine nucleotides are broken down of by the human body. High blood concetration of Uric Acid is known as hyperuricemia and is often associated with a wide range of disorders and medical conditions such as gout, diabetes and metabolic syndrome. Uric acid may be a marker of oxidative stress and may have a potential therapeutic role as an antioxidant.
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Ergänzende Hinweise
DefinitionA nitrogen compound produced from purines. In certain animals (e.g. birds and reptiles), it is the main excretory product resulting from breakdown of amino acids. In humans, uric acid crystals in the joints are the cause of gout.
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