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Record Information
Version2.0
Creation Date2014-09-11 02:06:17 UTC
Update Date2014-12-24 20:26:56 UTC
Accession NumberT3D4718
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.
Compound Type
  • Amide
  • Amine
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
5-(Di-2-chloroethyl)aminouracil
5-Aminouracil mustard
5-N,N-Bis(2-chloroethyl)aminouracil
5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione
5-[Di(beta-chloroethyl)amino]uracil
Aminouracil mustard
Uracil nitrogen mustard
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
SMILESOC1=NC=C(N(CCCl)CCCl)C(O)=N1
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 KeyInChIKey=IDPUKCWIGUEADI-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
LogP1.2
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frf-1930000000-b082a72f43cd6ef8d865JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-ee3938fb1cac655b6750JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r00-3690000000-e3d7d6c32273a27ea452JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-4900000000-c141e19ee451b1467b29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k96-6290000000-93d545f0c9fde44350d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9220000000-ee1cf7bef8946f7dc9feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-5577de19673152e348b9JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0w29-9730000000-047cc283312feb25a4edJSpectraViewer | MoNA
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00791
HMDB IDHMDB14929
PubChem Compound ID6194
ChEMBL IDCHEMBL1488
ChemSpider ID5959
KEGG IDC11686
UniProt IDNot Available
OMIM ID
ChEBI ID9884
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkUracil_mustard
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  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. [17016423 ]
  3. Hartley JA, Forrow SM, Souhami RL: Effect of ionic strength and cationic DNA affinity binders on the DNA sequence selective alkylation of guanine N7-positions by nitrogen mustards. Biochemistry. 1990 Mar 27;29(12):2985-91. [2337578 ]