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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:21:36 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060449
Secondary Accession Numbers
  • HMDB60449
Metabolite Identification
Common NameCarboxyphosphamide
DescriptionIn contrast to previous adult studies on urinary metabolites, plasma carboxyphosphamide concentrations did not support the existence of polymorphic metabolism. Plasma concentrations of dechlorethylcyclophosphamide and carboxyphosphamide were correlated in individual patients, suggesting that the activity of both aldehyde dehydrogenase and cytochrome P450 enzyme(s) determine carboxyphosphamide production in vivo. (PMID: 7850793 ) Detoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. (PMID: 9394035 ) A key finding was the detection of a metabolite, most likely carboxyphosphamide, that is formed only by cytosols from cells expressing either class 3 or class 1 ALDH. (PMID: 8662659 )
Structure
Data?1563866061
Synonyms
ValueSource
CarboxycyclophosphamideKegg
Carboxyphosphamide, (S)-isomerHMDB
Carboxyphosphamide, (R)-isomerHMDB
Chemical FormulaC7H15Cl2N2O4P
Average Molecular Weight293.085
Monoisotopic Molecular Weight292.014648904
IUPAC Name3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
Traditional Namecarboxyphosphamide
CAS Registry NumberNot Available
SMILES
NP(=O)(OCCC(O)=O)N(CCCl)CCCl
InChI Identifier
InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13)
InChI KeyQLAKAJLYYGOZQL-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
  • Phosphoric acid ester
  • Organic phosphoric acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Alkyl chloride
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.6 g/LALOGPS
logP0.37ALOGPS
logP-0.3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-0.069ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.86 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity61.47 m³·mol⁻¹ChemAxon
Polarizability25.75 ųChemAxon
Number of Rings0ChemAxon
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]+154.40130932474
DeepCCS[M-H]-152.04330932474
DeepCCS[M-2H]-186.0830932474
DeepCCS[M+Na]+160.8330932474
AllCCS[M+H]+158.032859911
AllCCS[M+H-H2O]+155.132859911
AllCCS[M+NH4]+160.732859911
AllCCS[M+Na]+161.432859911
AllCCS[M-H]-156.232859911
AllCCS[M+Na-2H]-157.332859911
AllCCS[M+HCOO]-158.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarboxyphosphamideNP(=O)(OCCC(O)=O)N(CCCl)CCCl3170.5Standard polar33892256
CarboxyphosphamideNP(=O)(OCCC(O)=O)N(CCCl)CCCl2022.3Standard non polar33892256
CarboxyphosphamideNP(=O)(OCCC(O)=O)N(CCCl)CCCl2183.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carboxyphosphamide,1TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl2254.1Semi standard non polar33892256
Carboxyphosphamide,1TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl2254.1Semi standard non polar33892256
Carboxyphosphamide,1TMS,isomer #2C[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl2286.6Semi standard non polar33892256
Carboxyphosphamide,1TMS,isomer #2C[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl2286.6Semi standard non polar33892256
Carboxyphosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl2264.9Semi standard non polar33892256
Carboxyphosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl2223.7Standard non polar33892256
Carboxyphosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl2881.3Standard polar33892256
Carboxyphosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl2394.4Semi standard non polar33892256
Carboxyphosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl2283.7Standard non polar33892256
Carboxyphosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl2974.6Standard polar33892256
Carboxyphosphamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2382.7Semi standard non polar33892256
Carboxyphosphamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2367.0Standard non polar33892256
Carboxyphosphamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2688.2Standard polar33892256
Carboxyphosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl2492.2Semi standard non polar33892256
Carboxyphosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl2492.2Semi standard non polar33892256
Carboxyphosphamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl2549.9Semi standard non polar33892256
Carboxyphosphamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl2549.9Semi standard non polar33892256
Carboxyphosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl2726.8Semi standard non polar33892256
Carboxyphosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl2633.5Standard non polar33892256
Carboxyphosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl3015.3Standard polar33892256
Carboxyphosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl2843.7Semi standard non polar33892256
Carboxyphosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl2645.9Standard non polar33892256
Carboxyphosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl3039.2Standard polar33892256
Carboxyphosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3046.1Semi standard non polar33892256
Carboxyphosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2868.2Standard non polar33892256
Carboxyphosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2883.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyphosphamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6950000000-ed4ce5a2a1fd50084a352017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyphosphamide GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9772000000-53be230f9ae27309a3c82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyphosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyphosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 10V, Positive-QTOFsplash10-004l-1090000000-a27d29f972437e499a042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 20V, Positive-QTOFsplash10-00di-9100000000-1e40a921ab23651791ff2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 40V, Positive-QTOFsplash10-01tc-9300000000-c25908f5c29c9ca8e9da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 10V, Negative-QTOFsplash10-004l-0190000000-a3cf2ab879262b59f4d72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 20V, Negative-QTOFsplash10-0j4i-9340000000-bcee68a2131ae01dbe362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 40V, Negative-QTOFsplash10-0udr-2910000000-53f914fcb1ee1ee017252017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 10V, Positive-QTOFsplash10-0006-0190000000-fca492ac2f0abff7a2032021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 20V, Positive-QTOFsplash10-00dl-0690000000-1d6bf5ada33e90cdb0aa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 40V, Positive-QTOFsplash10-08fr-9300000000-7e1a8c601be5439454ec2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 10V, Negative-QTOFsplash10-0006-0090000000-715bfb25b2641d2aa3112021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 20V, Negative-QTOFsplash10-00lu-1390000000-ddf7c49ccb61308735b32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyphosphamide 40V, Negative-QTOFsplash10-014i-4790000000-1f7d600b70ef82e0163f2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07646
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarboxycyclophosphamide
METLIN IDNot Available
PubChem Compound31515
PDB IDNot Available
ChEBI ID3410
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Dockham PA, Sreerama L, Sladek NE: Relative contribution of human erythrocyte aldehyde dehydrogenase to the systemic detoxification of the oxazaphosphorines. Drug Metab Dispos. 1997 Dec;25(12):1436-41. [PubMed:9394035 ]
  3. Yule SM, Boddy AV, Cole M, Price L, Wyllie R, Tasso MJ, Pearson AD, Idle JR: Cyclophosphamide metabolism in children. Cancer Res. 1995 Feb 15;55(4):803-9. [PubMed:7850793 ]
  4. Bunting KD, Townsend AJ: Protection by transfected rat or human class 3 aldehyde dehydrogenase against the cytotoxic effects of oxazaphosphorine alkylating agents in hamster V79 cell lines. Demonstration of aldophosphamide metabolism by the human cytosolic class 3 isozyme. J Biol Chem. 1996 May 17;271(20):11891-6. [PubMed:8662659 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails