Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:22 UTC
HMDB IDHMDB0015025
Secondary Accession Numbers
  • HMDB15025
Metabolite Identification
Common NameMechlorethamine
DescriptionMechlorethamine is only found in individuals that have used or taken this drug. It is a vesicant and necrotizing irritant destructive to mucous membranes. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem]Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.
Structure
Data?1676999902
Synonyms
ValueSource
2,2'-Dichloro-N-methyldiethylamineChEBI
beta,Beta'-dichlorodiethyl-N-methylamineChEBI
Bis(2-chloroethyl)methylamineChEBI
Bis(beta-chloroethyl)methylamineChEBI
ChlormethineChEBI
Methylbis(2-chloroethyl)amineChEBI
Methylbis(beta-chloroethyl)amineChEBI
N-Methyl-bis(2-chloroethyl)amineChEBI
N-Methyl-bis(beta-chloroethyl)amineChEBI
Nitrogen mustardChEBI
b,Beta'-dichlorodiethyl-N-methylamineGenerator
Β,beta'-dichlorodiethyl-N-methylamineGenerator
Bis(b-chloroethyl)methylamineGenerator
Bis(β-chloroethyl)methylamineGenerator
Methylbis(b-chloroethyl)amineGenerator
Methylbis(β-chloroethyl)amineGenerator
N-Methyl-bis(b-chloroethyl)amineGenerator
N-Methyl-bis(β-chloroethyl)amineGenerator
ChlorethazineHMDB
HN2HMDB
MBAHMDB
MechloroethamineHMDB
MecloretaminaHMDB
MustineHMDB
Mechlorethamine hydrochloride N oxideHMDB
Mechlorethamine hydrochloride N-oxideHMDB
Merck frosst brand OF mechlorethamine hydrochlorideHMDB
NSC-762HMDB
EmbichinHMDB
Hydrochloride N-oxide, mechlorethamineHMDB
Mechlorethamine N oxideHMDB
Mechlorethamine oxideHMDB
Merck brand OF mechlorethamine hydrochlorideHMDB
MitomenHMDB
Nitrogen mustard N oxideHMDB
CaryolysineHMDB
CloraminHMDB
Hydrochloride, mechlorethamineHMDB
MethylchlorethamineHMDB
N-Oxide, mechlorethamine hydrochlorideHMDB
N-Oxide, nitrogen mustardHMDB
Nitrogen mustard N-oxideHMDB
NitrogranulogenHMDB
NitrominHMDB
Mechlorethamine hydrochlorideHMDB
Mechlorethamine N-oxideHMDB
MustargenHMDB
NSC 762HMDB
Chemical FormulaC5H11Cl2N
Average Molecular Weight156.054
Monoisotopic Molecular Weight155.026854771
IUPAC Namebis(2-chloroethyl)(methyl)amine
Traditional Namemechlorethamine
CAS Registry Number51-75-2
SMILES
CN(CCCl)CCCl
InChI Identifier
InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
InChI KeyHAWPXGHAZFHHAD-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 amine
  • Tertiary amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point108 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility33.4 g/LNot Available
LogP1.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP1.31ALOGPS
logP1.52ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.67 m³·mol⁻¹ChemAxon
Polarizability15.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+132.67130932474
DeepCCS[M-H]-129.75230932474
DeepCCS[M-2H]-166.27830932474
DeepCCS[M+Na]+141.39330932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+135.732859911
AllCCS[M+Na]+136.832859911
AllCCS[M-H]-136.132859911
AllCCS[M+Na-2H]-139.632859911
AllCCS[M+HCOO]-143.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MechlorethamineCN(CCCl)CCCl1556.1Standard polar33892256
MechlorethamineCN(CCCl)CCCl1045.2Standard non polar33892256
MechlorethamineCN(CCCl)CCCl1088.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mechlorethamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9400000000-37f4081d8c3fd8e974c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mechlorethamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-66a0ef3007bd03bd93672014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 10V, Positive-QTOFsplash10-0a4i-0900000000-2282bef263bfa8a411232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 20V, Positive-QTOFsplash10-0a4i-7900000000-b0b770790e86670fc2a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 40V, Positive-QTOFsplash10-03di-9000000000-5d96975a96ed8783c02e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 10V, Negative-QTOFsplash10-0udi-1900000000-7801c92cb7dc490c200d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 20V, Negative-QTOFsplash10-0uxr-4900000000-0df7677828ba3d2293ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 40V, Negative-QTOFsplash10-08i3-9100000000-67d0e475a21ed8a44dca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 10V, Positive-QTOFsplash10-0a4i-0900000000-b39c5053cfb605f67e082021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 20V, Positive-QTOFsplash10-08fr-9400000000-9836caddbb3ebb21e8bb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 40V, Positive-QTOFsplash10-03di-9000000000-dcc5bf7c33b77979d5a52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 10V, Negative-QTOFsplash10-0ue9-8900000000-60357d33a598f0fa346f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mechlorethamine 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 DB00888 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00888 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 IDDB00888
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3893
KEGG Compound IDC07115
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMechlorethamine
METLIN IDNot Available
PubChem Compound4033
PDB IDNot Available
ChEBI ID28925
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