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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014929
Secondary Accession Numbers
  • HMDB14929
Metabolite Identification
Common NameUracil mustard
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. [PubChem]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.
Structure
Data?1582753236
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 Weight252.098
Monoisotopic Molecular Weight251.022832025
IUPAC Name5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nameuracil mustard
CAS Registry Number66-75-1
SMILES
ClCCN(CCCl)C1=CNC(=O)NC1=O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point206 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.32 g/LNot Available
LogP1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+147.14630932474
DeepCCS[M-H]-143.31430932474
DeepCCS[M-2H]-180.77830932474
DeepCCS[M+Na]+156.44330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Uracil mustardClCCN(CCCl)C1=CNC(=O)NC1=O2735.1Standard polar33892256
Uracil mustardClCCN(CCCl)C1=CNC(=O)NC1=O2182.9Standard non polar33892256
Uracil mustardClCCN(CCCl)C1=CNC(=O)NC1=O2428.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Uracil mustard,1TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O2197.3Semi standard non polar33892256
Uracil mustard,1TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O2319.7Standard non polar33892256
Uracil mustard,1TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O3072.2Standard polar33892256
Uracil mustard,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O2187.4Semi standard non polar33892256
Uracil mustard,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O2279.3Standard non polar33892256
Uracil mustard,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O3026.2Standard polar33892256
Uracil mustard,2TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O2262.3Semi standard non polar33892256
Uracil mustard,2TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O2376.8Standard non polar33892256
Uracil mustard,2TMS,isomer #1C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O2713.9Standard polar33892256
Uracil mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O2475.2Semi standard non polar33892256
Uracil mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O2553.8Standard non polar33892256
Uracil mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O3061.6Standard polar33892256
Uracil mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O2423.0Semi standard non polar33892256
Uracil mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O2514.6Standard non polar33892256
Uracil mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O2999.9Standard polar33892256
Uracil mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2717.6Semi standard non polar33892256
Uracil mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2811.5Standard non polar33892256
Uracil mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2783.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Uracil mustard GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frf-1930000000-b082a72f43cd6ef8d8652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uracil mustard GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uracil mustard GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0w29-9730000000-047cc283312feb25a4ed2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 10V, Positive-QTOFsplash10-0udi-0190000000-ee3938fb1cac655b67502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 20V, Positive-QTOFsplash10-0r00-3690000000-e3d7d6c32273a27ea4522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 40V, Positive-QTOFsplash10-02t9-4900000000-c141e19ee451b1467b292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 10V, Negative-QTOFsplash10-0k96-6290000000-93d545f0c9fde44350d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 20V, Negative-QTOFsplash10-0006-9220000000-ee1cf7bef8946f7dc9fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 40V, Negative-QTOFsplash10-0006-9400000000-5577de19673152e348b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 10V, Positive-QTOFsplash10-0udi-0090000000-5f08b1b5a345ae125a3f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 20V, Positive-QTOFsplash10-0udi-0490000000-86e8889e895d31e6b5a42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 40V, Positive-QTOFsplash10-0w4i-3900000000-73fd22078502352231062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 10V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 20V, Negative-QTOFsplash10-001i-9310000000-abaab02ed488d29cc3392021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uracil mustard 40V, Negative-QTOFsplash10-001i-9500000000-fffdc9aec429e51493802021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00791 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00791 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00791
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5959
KEGG Compound IDC11686
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUramustine
METLIN IDNot Available
PubChem Compound6194
PDB IDNot Available
ChEBI ID9884
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available