Basic information
- CAS
69-93-2- Standard SMILES
O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1- InChIKey
LEHOTFFKMJEONL-UHFFFAOYSA-N- Molecular formula
- C5H4N4O3
- Average molar mass
- 168.11 g/mol
- Monoisotopic mass
- 168.02833999
Overview
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.
Names & identifiers
- Preferred name
- Uric Acid
- IUPAC
- 7,9-dihydro-3H-purine-2,6,8-trione
- English name
- Uric acid
- Molecular formula
- C5H4N4O3
- Molecular weight
- 168.11
Names & synonyms
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
Show more names
TRIKETOPURINEUric aciNSC 3975URIC OXIDEUricAcidGrURIC ACID(RG)
2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneUricum acidumIdelalisib metabolite m54trioxopurineDTXSID3042508NSC-3975268B43MJ25DTXCID1022508
Database identifiers
- CAS
69-93-2- PubChem CID
- 1175
- DTXSID
DTXSID3042508- ChEMBL
CHEMBL792- ChEBI
CHEBI:17775- UNII
- 268B43MJ25
- EC Number
- 200-720-7
- Nikkaji
- J2.372H
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 99.3 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 332
Experimental & physicochemical properties
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]+
Physicochemical properties
- Melting point
- 300 °C · >300 °C (lit.)
- Boiling point
- 297.02 °C · 297.02°C (rough estimate)
- Density
- 1 · 1,9 g/cm3
- refractive index
- 1.99 · 1.9900 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Aqueous Base (Sparingly, Heated)
- pka
- 3.89 · 3.89(at 12℃)
- form
- crystalline
- color
- White to off-white
- Odor
- Odorless
- biological source
- animal (seabird feces (guano))
- Water Solubility
- 1 M · Soluble in 1M sodium hydroxide solution. Slightly soluble in water. Insoluble in ether and alcohol.
- Specific Heat Capacity
- 0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
- Merck
- 14 · 14,9875
- BRN
- 156158 · 156158
- Stability
- Stable. Incompatible with acids, bases, oxidising agents.
- Cosmetics Ingredients Functions
- 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 DataBase Reference
- 69 · 69-93-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- uric acid
- FDA UNII
- 268 B43MJ25 · 268B43MJ25
- EPA Substance Registry System
- Uric acid (69-93-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 55 · NA.55
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 33 · 33-36/37/38
- Safety Statements
- 24 · 24/25-36-26
- WGK Germany
- 3 · 3
- RTECS
- 7050080 · YU7050080
- TSCA
- TSCA listed
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 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.
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
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
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YU7050080
- hs_code
- 29339900
- Toxicity
- 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.
- risk_code
- 33-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H332-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Pharmacology
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)
Uses & manufacturing
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
Applications
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.
UsesUric 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.
Upstream & downstream products
Downstream products
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Additional notes
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.
Definitionuric acid: The end product of purinebreakdown in most primates, birds,terrestrial reptiles, and insects andalso (except in primates) the majorform in which metabolic nitrogen isexcreted. Being fairly insoluble, uricacid can be expelled in solid form,which conserves valuable water inarid environments. The accumulationof uric acid in the synovial uidof joints causes gout.
Related reactions
10 records
Compound notes
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