5-Bromouracil (CHEM001540)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2016-11-09 01:08:34 UTC
Accession NumberCHEM001540
Identification
Common Name5-Bromouracil
ClassSmall Molecule
Description5-bromouracil is brominated derivative of uracil that acts as an antimetabolite or base analog, substituting for thymine in DNA. It can induce DNA mutations in the same way as 2-aminopurine. It is used mainly as an experimental mutagen, but its deoxyriboside derivative (5-bromo-2-deoxyuridine) is used to treat neoplasms. 5-bromouracil can be generated naturally, within the body, from uracil by either eosinophil peroxidase or myeloperoxidase. These enzymes preferentially brominate uracil at plasma concentrations of bromine and under moderately acidic conditions.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-Tetrahydro-5-bromo-2,4-pyrimidinedioneChEBI
5-Bromo-2,4(1H,3H)-pyrimidinedioneChEBI
5-BrUChEBI
5-BUChEBI
BromouracilChEBI
5 BromouracilMeSH
BromuracilMeSH
Chemical FormulaC4H3BrN2O2
Average Molecular Mass190.983 g/mol
Monoisotopic Mass189.938 g/mol
CAS Registry Number51-20-7
IUPAC Name5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namebromouracil
SMILESBrC1=CNC(=O)NC1=O
InChI IdentifierInChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI KeyLQLQRFGHAALLLE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. 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 ParentHalopyrimidines
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Halopyrimidine
  • Aryl halide
  • Aryl bromide
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point310°C
Boiling PointNot Available
Solubility0.815 mg/mL [GUNTHER,FA et al. (1968)]
Predicted Properties
PropertyValueSource
Water Solubility4.75 g/LALOGPS
logP-0.1ALOGPS
logP-0.03ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.13ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.58 m³·mol⁻¹ChemAxon
Polarizability12.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-3a083d7a254f02ae1d66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-c7659146e2d62891c141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-5900000000-6c9736365d3f4619558fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-6900000000-2859f1a95bc39decb00dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-0c7a53d2d2416a9c8564Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-84558ca4912270154af2Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-3900000000-c3f1f4cbe37bd2041f68Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityThymidine phosphorylase, a pyrimidine salvage enzyme, transforms 5-bromouracil to 5-bromodeoxyuridine, a mutagenic analogue of thymidine. Ultimately, 5-bromouracil acts on DNA. It induces a random DNA point mutation via base substitution. The base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles, depending on whether 5-BrU is within the DNA molecule or is an incoming base when it is enolized or ionized. 5-Bromouracil normally pairs with adenine. However, the proportion of 5-bromouracil in the enol tautomer is higher than that of thymine because the bromine atom is more electronegative than is a methyl group on the C-5 atom. Thus, the incorporation of 5-bromouracil is especially likely to cause altered base-pairing in a subsequent round of DNA replication.
Metabolism5-bromouracil is metabolized into 5-bromodeoxyuridine via thymidine phosphorylase. (1)
Toxicity ValuesLD50: 1700 mg/kg (Rat, Intraperitoneal); LD50 1400 mg/kg (Mouse, Intraperitoneal) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. May cause heritable genetic damage.
Uses/SourcesLaboratory chemical used as a mutagen in many mutagenesis experiments.
Minimum Risk LevelNot Available
Health Effects 5-bromouracil is a mutagen (causes mutations) and a carcinogen. It can cause respiratory tract irritation if inhaled, skin irritation if it contacts the skin and eye irritation if it contacts the eyes.
Symptoms5-bromouracil can cause hypermotility, diarrhea, weight loss and possibly death if large amounts are repeatedly ingested.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link5-Bromouracil
Chemspider IDNot Available
ChEBI ID20552
PubChem Compound ID5802
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14522043
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28320905
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3950402