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Identification
NameUracil
Accession NumberDB03419  (EXPT03201)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number66-22-8
WeightAverage: 112.0868
Monoisotopic: 112.027277382
Chemical FormulaC4H4N2O2
InChI KeyISAKRJDGNUQOIC-UHFFFAOYSA-N
InChI
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
IUPAC Name
1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
O=C1NC=CC(=O)N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassDiazines
SubclassPyrimidines and Pyrimidine Derivatives
Direct parentPyrimidones
Alternative parentsHydropyrimidines; Polyamines
Substituentshydropyrimidine; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the pyrimidones. These are compounds whose pyrimidine ring bears a ketone.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Beta-Alanine MetabolismMetabolicSMP00007
GABA-Transaminase DeficiencyDiseaseSMP00351
Carnosinuria, carnosinemiaDiseaseSMP00493
Ureidopropionase deficiencyDiseaseSMP00492
Beta Ureidopropionase DeficiencyDiseaseSMP00172
UMP Synthase Deiciency (Orotic Aciduria)DiseaseSMP00219
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)DiseaseSMP00202
Pyrimidine MetabolismMetabolicSMP00046
Dihydropyrimidinase DeficiencyDiseaseSMP00178
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9591
Blood Brain Barrier + 0.9907
Caco-2 permeable - 0.8957
P-glycoprotein substrate Non-substrate 0.785
P-glycoprotein inhibitor I Non-inhibitor 0.9543
P-glycoprotein inhibitor II Non-inhibitor 0.9968
Renal organic cation transporter Non-inhibitor 0.9073
CYP450 2C9 substrate Non-substrate 0.7561
CYP450 2D6 substrate Non-substrate 0.8331
CYP450 3A4 substrate Non-substrate 0.793
CYP450 1A2 substrate Non-inhibitor 0.7271
CYP450 2C9 substrate Non-inhibitor 0.9713
CYP450 2D6 substrate Non-inhibitor 0.9719
CYP450 2C19 substrate Non-inhibitor 0.981
CYP450 3A4 substrate Non-inhibitor 0.9707
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.993
Ames test Non AMES toxic 0.9178
Carcinogenicity Non-carcinogens 0.9471
Biodegradation Ready biodegradable 0.7648
Rat acute toxicity 1.2228 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9614
hERG inhibition (predictor II) Non-inhibitor 0.968
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point338 °CPhysProp
water solubility3600 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.07HANSCH,C ET AL. (1995)
logS-1.48ADME Research, USCD
Caco2 permeability-5.37ADME Research, USCD
pKa9.45MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility26.5ALOGPS
logP-1.2ALOGPS
logP-0.86ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)9.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.97 m3·mol-1ChemAxon
Polarizability9.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Kurt Klemm, Wolfgang Schoetensack, Wolfgang Prusse, “Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production.” U.S. Patent US3957786, issued September, 1951.

US3957786
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00027
KEGG CompoundC00106
PubChem Compound1174
PubChem Substance46504697
ChEBI17568
ChEMBL
HETURA
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Ribosomal small subunit pseudouridine synthase A

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribosomal small subunit pseudouridine synthase A P0AA43 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Uracil-DNA glycosylase

Kind: protein

Organism: HHV-1

Pharmacological action: unknown

Components

Name UniProt ID Details
Uracil-DNA glycosylase P10186 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Uracil-DNA glycosylase

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: unknown

Components

Name UniProt ID Details
Uracil-DNA glycosylase Q8X444 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Dihydropyrimidine dehydrogenase [NADP(+)]

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydropyrimidine dehydrogenase [NADP(+)] Q12882 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Uridine-cytidine kinase-like 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Uridine-cytidine kinase-like 1 Q9NWZ5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

6. Uracil-DNA glycosylase

Kind: protein

Organism: Thermus thermophilus

Pharmacological action: unknown

Components

Name UniProt ID Details
Uracil-DNA glycosylase Q7WYV4 Details

7. Pyrimidine-nucleoside phosphorylase

Kind: protein

Organism: Geobacillus stearothermophilus

Pharmacological action: unknown

Components

Name UniProt ID Details
Pyrimidine-nucleoside phosphorylase P77836 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:21