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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014436
Secondary Accession Numbers
  • HMDB14436
Metabolite Identification
Common NameChlorambucil
DescriptionChlorambucil, also known as ambochlorin or chloraminophen, 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. Chlorambucil is a drug which is used for treatment of chronic lymphatic (lymphocytic) leukemia, childhood minimal-change nephrotic syndrome, and malignant lymphomas including lymphosarcoma, giant follicular lymphoma, hodgkin's disease, non-hodgkin's lymphomas, and waldenström’s macroglobulinemia. Chlorambucil is a moderately basic compound (based on its pKa). Chlorambucil is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.
Structure
Data?1582753179
Synonyms
ValueSource
4-(p-Bis(beta-chloroethyl)aminophenyl)butyric acidChEBI
4-[p-[Bis(2-chloroethyl)amino]phenyl]butyric acidChEBI
AmbochlorinChEBI
ChloraminophenChEBI
gamma-[p-Di(2-chloroethyl)aminophenyl]butyric acidChEBI
LeukeranChEBI
N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyric acidChEBI
Phenylbutyric acid nitrogen mustardChEBI
4-(p-Bis(b-chloroethyl)aminophenyl)butyrateGenerator
4-(p-Bis(b-chloroethyl)aminophenyl)butyric acidGenerator
4-(p-Bis(beta-chloroethyl)aminophenyl)butyrateGenerator
4-(p-Bis(β-chloroethyl)aminophenyl)butyrateGenerator
4-(p-Bis(β-chloroethyl)aminophenyl)butyric acidGenerator
4-[p-[Bis(2-chloroethyl)amino]phenyl]butyrateGenerator
g-[p-Di(2-chloroethyl)aminophenyl]butyrateGenerator
g-[p-Di(2-chloroethyl)aminophenyl]butyric acidGenerator
gamma-[p-Di(2-chloroethyl)aminophenyl]butyrateGenerator
Γ-[p-di(2-chloroethyl)aminophenyl]butyrateGenerator
Γ-[p-di(2-chloroethyl)aminophenyl]butyric acidGenerator
N,N-Di-2-chloroethyl-g-p-aminophenylbutyrateGenerator
N,N-Di-2-chloroethyl-g-p-aminophenylbutyric acidGenerator
N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyrateGenerator
N,N-Di-2-chloroethyl-γ-p-aminophenylbutyrateGenerator
N,N-Di-2-chloroethyl-γ-p-aminophenylbutyric acidGenerator
Phenylbutyrate nitrogen mustardGenerator
ChlocambucilHMDB
ChloraminopheneHMDB
ChlorbutinHMDB
ChlorbutineHMDB
ChloroambucilHMDB
ChlorobutinHMDB
ChlorobutineHMDB
LympholysinHMDB
4-(Bis(2-chloroethyl)amino)benzenebutanoic acidHMDB
AmboclorinHMDB
Glaxo wellcome brand OF chlorambucilHMDB
GlaxoSmithKline brand OF chlorambucilHMDB
N,N-Di-(2-chloroethyl)-p-aminophenylbutyric acidHMDB
Wellcome brand OF chlorambucilHMDB
Chemical FormulaC14H19Cl2NO2
Average Molecular Weight304.212
Monoisotopic Molecular Weight303.079284271
IUPAC Name4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
Traditional Namechlorambucil
CAS Registry Number305-03-3
SMILES
OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl
InChI Identifier
InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)
InChI KeyJCKYGMPEJWAADB-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
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Nitrogen mustard
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl chloride
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.077 g/LNot Available
LogP3.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available168.701http://allccs.zhulab.cn/database/detail?ID=AllCCS00000700
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP3.81ALOGPS
logP3.94ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity79.68 m³·mol⁻¹ChemAxon
Polarizability31.98 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]+165.34130932474
DeepCCS[M-H]-162.98330932474
DeepCCS[M-2H]-195.90530932474
DeepCCS[M+Na]+171.43530932474
AllCCS[M+H]+165.132859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+167.932859911
AllCCS[M+Na]+168.732859911
AllCCS[M-H]-169.232859911
AllCCS[M+Na-2H]-169.632859911
AllCCS[M+HCOO]-170.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorambucilOC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl3575.0Standard polar33892256
ChlorambucilOC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl2477.9Standard non polar33892256
ChlorambucilOC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl2455.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chlorambucil,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C12456.6Semi standard non polar33892256
Chlorambucil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C12706.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlorambucil GC-MS (Non-derivatized) - 70eV, Positivesplash10-066u-2790000000-bf4786edba412b2ccaae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorambucil GC-MS (1 TMS) - 70eV, Positivesplash10-024i-5393000000-3be6fe379684458bfa852017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorambucil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2491000000-ddb7d5da8316562dba362014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorambucil LC-ESI-qTof , Positive-QTOFsplash10-004i-0002900000-472e293a011d716bb5a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorambucil , positive-QTOFsplash10-0zfr-0519000000-1bca00472dfc8c30a4652017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 10V, Positive-QTOFsplash10-0udr-0096000000-3899963778fe2e6e88de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 20V, Positive-QTOFsplash10-08g0-3591000000-6ae3349b3f490c58310d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 40V, Positive-QTOFsplash10-0j4i-6920000000-15483700b73ee5d5c44b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 10V, Negative-QTOFsplash10-0udi-0039000000-b8ff9ca35aa22b00bd352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 20V, Negative-QTOFsplash10-0uxr-1193000000-7606e0823853c0c258ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 40V, Negative-QTOFsplash10-052f-9540000000-f5720e555315984712a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 10V, Negative-QTOFsplash10-001i-9004000000-788a1a6f740556f914412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 20V, Negative-QTOFsplash10-001i-9000000000-724cdb1db65352c21f6c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 40V, Negative-QTOFsplash10-001i-9100000000-58ace4115f9b048a722e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 10V, Positive-QTOFsplash10-0udr-0098000000-d1dce37c9e184d7829de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 20V, Positive-QTOFsplash10-00kr-0091000000-f4d0cc5c505d1414f7cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorambucil 40V, Positive-QTOFsplash10-014m-1920000000-59f8073bfe41e45f2bdb2021-09-24Wishart 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 DB00291 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00291 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 IDDB00291
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2607
KEGG Compound IDC06900
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorambucil
METLIN IDNot Available
PubChem Compound2708
PDB IDNot Available
ChEBI ID28830
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. [PubMed:11114313 ]
  2. Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. doi: 10.1002/14651858.CD006719.pub3. [PubMed:19160296 ]

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular weight:
23355.625
References
  1. Parker LJ, Ciccone S, Italiano LC, Primavera A, Oakley AJ, Morton CJ, Hancock NC, Bello ML, Parker MW: The anti-cancer drug chlorambucil as a substrate for the human polymorphic enzyme glutathione transferase P1-1: kinetic properties and crystallographic characterisation of allelic variants. J Mol Biol. 2008 Jun 27;380(1):131-44. doi: 10.1016/j.jmb.2008.04.066. Epub 2008 May 4. [PubMed:18511072 ]
  2. Zhang J, Lou YJ: Relationship between activation of microsomal glutathione S-transferase and metabolism behavior of chlorambucil. Pharmacol Res. 2003 Dec;48(6):623-30. [PubMed:14527828 ]