| Common Name |
1,3-Dimethyluracil
| Description |
1,3-Dimethyluracil is a methyl derivative of uric acid, found occasionally in human urine. 1,3-Dimethyluracil is one of the purine component in urinary calclii. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calclii colid be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general popliation, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. (PMID: 11712316 , 15833286 , 3506820 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2,4-Dihydroxy-1,3-dimethylpyrimidineChEBI
N,N'-dimethyluracilChEBI
N1,N3-DimethyluracilChEBI
1, 3-Dimethyl-2,4(1H,3H)-pyrimidinedioneHMDB
1,3-Dimethyl-2,4(1H,3H)-pyrimidinedioneHMDB
| Chemical Formlia |
C6H8N2O2
| Average Molecliar Weight |
140.1399
| Monoisotopic Molecliar Weight |
140.05857751
| IUPAC Name |
1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
| Traditional Name |
1,3-dimethyluracil
| CAS Registry Number |
874-14-6
| SMILES |
CN1C=CC(=O)N(C)C1=O
| InChI Identifier |
InChI=1S/C6H8N2O2/c1-7-4-3-5(9)8(2)6(7)10/h3-4H,1-2H3
| InChI Key |
JSDBKAHWADVXFU-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Diazines
| Direct Parent |
Pyrimidones
| Alternative Parents |
Hydropyrimidines
Vinylogous amides
Heteroaromatic compounds
Ureas
Lactams
Azacyclic compounds
Organopnictogen compounds
Organooxygen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Pyrimidone
Hydropyrimidine
Heteroaromatic compound
Vinylogous amide
Urea
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
pyrimidone (CHEBI:74763 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point120 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.54HANSCH,C ET AL. (1995)
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility270.0 mg/mLALOGPS
logP-0.81ALOGPS
logP-0.41ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.76 m3·mol-1ChemAxon
Polarizability13.45 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022866
| KNApSAcK ID |
Not Available
| Chemspider ID |
63310
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02144
| Metagene Link |
HMDB02144
| METLIN ID |
Not Available
| PubChem Compound |
70122
| PDB ID |
Not Available
| ChEBI ID |
108884
Product: Mutant IDH1-IN-2
References |
| Synthesis Reference |
Harada, Kaoru; Suzuki, Shinnichiro. The new synthesis of uracil and 1,3-dimethyluracil. Tetrahedron Letters (1976), (27), 2321-2. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
- Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
- Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
|
PMID: 15525762