Uracil mustard (CHEM003676)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-11 02:06:17 UTC
Update Date2026-04-04 10:40:05 UTC
Accession NumberCHEM003676
Identification
Common NameUracil mustard
ClassSmall Molecule
DescriptionUracil mustard is only found in individuals that have used or taken this drug. It is a nitrogen mustard derivative of uracil. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage. After activation, uracil mustard binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
Contaminant Sources
  • Clean Air Act Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-(Di-2-chloroethyl)aminouracilChEBI
5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedioneChEBI
5-[Di(beta-chloroethyl)amino]uracilChEBI
5-Aminouracil mustardChEBI
5-N,N-Bis(2-chloroethyl)aminouracilChEBI
Aminouracil mustardChEBI
Uracil nitrogen mustardChEBI
UramustineKegg
5-[Di(b-chloroethyl)amino]uracilGenerator
5-[Di(β-chloroethyl)amino]uracilGenerator
Mustard, uracilHMDB
5-(Bis(2-chloroethyl)amino)-2,4-(1H,3H)pyrimidinedioneHMDB
Uracil mustardChEBI
Chemical FormulaC8H11Cl2N3O2
Average Molecular Mass252.098 g/mol
Monoisotopic Mass251.023 g/mol
CAS Registry Number66-75-1
IUPAC Name5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nameuracil mustard
SMILESClCCN(CCCl)C1=CNC(=O)NC1=O
InChI IdentifierInChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
InChI KeyIDPUKCWIGUEADI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Tertiary amine
  • Urea
  • Organoheterocyclic compound
  • Azacycle
  • Alkyl halide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl chloride
  • Organopnictogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point206°C
Boiling PointNot Available
Solubility1070 mg/L
Predicted Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
logP0.79ALOGPS
logP0.41ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)1.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.35 m³·mol⁻¹ChemAxon
Polarizability22.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frf-1930000000-b082a72f43cd6ef8d865Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-ee3938fb1cac655b6750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r00-3690000000-e3d7d6c32273a27ea452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-4900000000-c141e19ee451b1467b29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k96-6290000000-93d545f0c9fde44350d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9220000000-ee1cf7bef8946f7dc9feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-5577de19673152e348b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-5f08b1b5a345ae125a3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0490000000-86e8889e895d31e6b5a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w4i-3900000000-73fd2207850235223106Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9310000000-abaab02ed488d29cc339Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9500000000-fffdc9aec429e5149380Spectrum
MSMass Spectrum (Electron Ionization)splash10-0w29-9730000000-047cc283312feb25a4edSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAfter activation, it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesUsed for its antineoplastic properties.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00791
HMDB IDHMDB0014929
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkUramustine
Chemspider ID5959
ChEBI ID9884
PubChem Compound ID6194
Kegg Compound IDC11686
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available