5-Bromouracil (T3D1790)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2014-12-24 20:24:38 UTC
Accession NumberT3D1790
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.
Compound Type
  • Amide
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,2,3,4-tetrahydro-5-bromo-2,4-pyrimidinedione
2,4-Pyrimidinedione, 1,2,3,4-tetrahydro-5-bromo
5-Bromo-2,4(1H,3H)-pyrimidinedione
5-Bromo-2,4-dihydroxypyrimidine
5-Bromo-2,4-pyrimidinediol
5-bromopyrimidine-2,4(1H,3H)-dione
Bromouracil
Bromuracil
C4H3BrN2O2
Uracil, 5-bromo-
URB
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 KeyInChIKey=LQLQRFGHAALLLE-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)]
LogPNot Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-3a083d7a254f02ae1d662016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-c7659146e2d62891c1412016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-5900000000-6c9736365d3f4619558f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-6900000000-2859f1a95bc39decb00d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-0c7a53d2d2416a9c85642016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-84558ca4912270154af22016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-3900000000-c3f1f4cbe37bd2041f682014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
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. (4)
Toxicity ValuesLD50: 1700 mg/kg (Rat, Intraperitoneal); LD50 1400 mg/kg (Mouse, Intraperitoneal) (1)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5802
ChEMBL IDCHEMBL144730
ChemSpider ID5597
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID20552
BioCyc IDNot Available
CTD IDD001976
Stitch ID5-Bromouracil
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1790.pdf
General References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. Wikipedia. 5-Bromouracil. Last Updated 21 May 2009. [Link]
  4. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. Wikipedia. 5-Bromouracil. Last Updated 21 May 2009. [Link]
Target Details
2. Thymidine phosphorylase
General Function:
Transferase activity, transferring pentosyl groups
Specific Function:
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro.Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
TYMP
Uniprot ID:
P19971
Molecular Weight:
49954.965 Da
References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. Wikipedia. 5-Bromouracil. Last Updated 21 May 2009. [Link]
Target Details
3. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]