Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014672
Secondary Accession Numbers
  • HMDB14672
Metabolite Identification
Common NameCyclophosphamide
DescriptionCyclophosphamide, also known as cytoxan or cytophosphan, 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. In humans, cyclophosphamide is involved in the cyclophosphamide action pathway. Cyclophosphamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Cyclophosphamide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Cyclophosphamide.
Structure
Data?1582753206
Synonyms
ValueSource
(+-)-CyclophosphamideChEBI
(RS)-CyclophosphamideChEBI
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxideChEBI
Bis(2-chloroethyl)phosphoramide cyclic propanolamide esterChEBI
Cyclophosphamide anhydrousChEBI
N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxideChEBI
CytoxanKegg
Cyclophosphamide monohydrateHMDB
CytophosphanHMDB
SendoxanHMDB
Anhydrous, cyclophosphamideHMDB
Cyclophosphamide, (S)-isomerHMDB
CyclophosphaneHMDB
CytophosphaneHMDB
EndoxanHMDB
NeosarHMDB
Cyclophosphamide, (R)-isomerHMDB
Monohydrate, cyclophosphamideHMDB
ProcytoxHMDB
(+,-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrateHMDB
Chemical FormulaC7H15Cl2N2O2P
Average Molecular Weight261.086
Monoisotopic Molecular Weight260.02481966
IUPAC Name2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
Traditional Name2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
CAS Registry Number6055-19-2
SMILES
ClCCN(CCCl)P1(=O)NCCCO1
InChI Identifier
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChI KeyCMSMOCZEIVJLDB-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
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Oxazaphosphinane
  • Organic phosphoric acid amide
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl chloride
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 - 45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.1 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available146.525http://allccs.zhulab.cn/database/detail?ID=AllCCS00000702
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.1 g/LALOGPS
logP0.76ALOGPS
logP0.097ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.43ChemAxon
pKa (Strongest Basic)0.084ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.48 m³·mol⁻¹ChemAxon
Polarizability23.72 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]+154.38430932474
DeepCCS[M-H]-151.2330932474
DeepCCS[M-2H]-187.76730932474
DeepCCS[M+Na]+163.4330932474
AllCCS[M+H]+152.432859911
AllCCS[M+H-H2O]+148.932859911
AllCCS[M+NH4]+155.632859911
AllCCS[M+Na]+156.532859911
AllCCS[M-H]-150.432859911
AllCCS[M+Na-2H]-151.532859911
AllCCS[M+HCOO]-152.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclophosphamideClCCN(CCCl)P1(=O)NCCCO12753.1Standard polar33892256
CyclophosphamideClCCN(CCCl)P1(=O)NCCCO11805.4Standard non polar33892256
CyclophosphamideClCCN(CCCl)P1(=O)NCCCO12041.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl2041.3Semi standard non polar33892256
Cyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl1917.6Standard non polar33892256
Cyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl2667.1Standard polar33892256
Cyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl2272.9Semi standard non polar33892256
Cyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl2163.3Standard non polar33892256
Cyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl2799.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-2930000000-a5e2529d99bd261703f02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-08fr-9470000000-53f4a8ff83c415492e032014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOFsplash10-0059-1490000000-36d8ebdb421248c38c7b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOFsplash10-03di-1390000000-b8dc1a824ec33e3882132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOFsplash10-03di-0390000000-66983035d1db7ac36bd62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-001l-0970000000-939110a705ed71803ab82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-2bdfe4296c2bdf8d4a992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0190000000-1e8e017f8e39fa5d73cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0930000000-d7459c8d20a8fc59f6f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-33cb20e845200f9d26182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-2900000000-09d33a8387b9d152f24a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-01ox-6900000000-cdebe09ff6df7c25b4772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-d749f27c3144da2c431c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0190000000-a6fa921df18384671a7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0930000000-abdb40162fc8a44200f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-8c0705ee62a5f9c7d44e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-2900000000-a299026342c77e92c48c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-01ox-6900000000-fc2845c75bbccc83ad992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-001l-0970000000-83e0f5b88b6fbe0a1ea72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-5490a2b493bfde967fa32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-456626f46e480e0ac6702017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Positive-QTOFsplash10-0006-9150000000-28408c9f0486cc7568f22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Positive-QTOFsplash10-052f-9600000000-fd85ba5646421fb4dd682016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Positive-QTOFsplash10-0006-9100000000-dc67f093f2419f82cb182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Negative-QTOFsplash10-0002-1920000000-ef90686fe8c9da71ccd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Negative-QTOFsplash10-0a4i-9000000000-c974342f3a086d037df62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Negative-QTOFsplash10-002u-9600000000-142aeef910da3ef2f6b32016-08-03Wishart 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00531 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00531 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>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 IDDB00531
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2804
KEGG Compound IDC07888
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclophosphamide
METLIN IDNot Available
PubChem Compound2907
PDB IDNot Available
ChEBI ID4027
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 References
  1. Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. [PubMed:2491747 ]
  2. Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. [PubMed:8697402 ]
  3. (). FDA label . .