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Identification
NameUracil
Accession NumberDB03419  (EXPT03201)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number66-22-8
WeightAverage: 112.0868
Monoisotopic: 112.027277382
Chemical FormulaC4H4N2O2
InChI KeyInChIKey=ISAKRJDGNUQOIC-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9591
Blood Brain Barrier+0.9907
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.785
P-glycoprotein inhibitor INon-inhibitor0.9543
P-glycoprotein inhibitor IINon-inhibitor0.9968
Renal organic cation transporterNon-inhibitor0.9073
CYP450 2C9 substrateNon-substrate0.7561
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.793
CYP450 1A2 substrateNon-inhibitor0.7271
CYP450 2C9 inhibitorNon-inhibitor0.9713
CYP450 2D6 inhibitorNon-inhibitor0.9719
CYP450 2C19 inhibitorNon-inhibitor0.981
CYP450 3A4 inhibitorNon-inhibitor0.9707
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.993
Ames testNon AMES toxic0.9178
CarcinogenicityNon-carcinogens0.9471
BiodegradationReady biodegradable0.7648
Rat acute toxicity1.2228 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9614
hERG inhibition (predictor II)Non-inhibitor0.968
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility26.5 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-kzl0000000-18425875415ad150c4fcView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-zrg0000000-e884a4b98e7e9dc75e5fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-utz0000000-026cb6beb5cde6a61b80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-cz00000000-e422eda255a4b6414f86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z300000000-130eb5f4414426e03667View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z500000000-c096d08ca715d97cd732View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-z900000000-83a0a6ad4fc1b407e570View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-zf00000000-acd0cfd54af7d6a55283View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0z00000000-309fe212c929f3c6a930View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-oz00000000-55a7de75a40eab61da8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-1c3caab26eb7e359db92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-7494d4e611a73ecb79eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-z000000000-ed4046b040337db620d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-2z00000000-ff54f3083ce4ccccfd95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0z00000000-6728c1eb6f68b40c09f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-5z00000000-0029cbdcaa1377a4d03eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-zh00000000-c227e1deb392170cb323View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-z000000000-3cf6f9fc3ab6890266acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-iz00000000-67a3d94ab649e28bda13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-z400000000-bbf50de54fc413b6588eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-z000000000-98042b91f1087b0c2563View in MoNA
MSMass Spectrum (Electron Ionization)splash10-zf00000000-d7ffe72f606f1af3349bView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 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

2. 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

3. 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

4. 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

5. 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

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