ContaminantDB: 2-Dechloroethylifosfamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:17:04 UTC

Update Date

2016-11-09 01:17:24 UTC

Accession Number

CHEM021966

Identification

Common Name

2-Dechloroethylifosfamide

Class

Small Molecule

Description

2-Dechloroethylifosfamide is a metabolite of the antitumor, alkylating drug Ifosfamide. 2-dechloroethylifosfamide is a member of the compound class known as oxazaphosphorines. Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. 2-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of cytochrome P450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221). 2-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-DClIF	HMDB
2-DCE-iff	HMDB
2-Amino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazophosphorine-2-O-xide	HMDB
Dechloroethylifosfamide, (+-)-isomer	HMDB
Dechloroethylifosfamide, (R)-isomer	HMDB
Dechloroethylifosfamide, (S)-isomer	HMDB
Dechloroethylifosfamide	HMDB

Chemical Formula

C₅H₁₂ClN₂O₂P

Average Molecular Mass

198.588 g/mol

Monoisotopic Mass

198.032 g/mol

CAS Registry Number

53459-55-5

IUPAC Name

2-amino-3-(2-chloroethyl)-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

dechloroethylifosfamide

SMILES

NP1(=O)OCCCN1CCCl

InChI Identifier

InChI=1S/C5H12ClN2O2P/c6-2-4-8-3-1-5-10-11(8,7)9/h1-5H2,(H2,7,9)

InChI Key

ROGLJLJCDSTWBN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Organic phosphoramides

Direct Parent

Phosphoric monoester diamides

Alternative Parents

Substituents

Phosphoric monoester diamide
Oxazaphosphinane
Organoheterocyclic compound
Azacycle
Oxacycle
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organonitrogen heterocyclic compound (CHEBI:80562 )
organophosphorus compound (CHEBI:80562 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	46.3 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	-0.79	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Acidic)	14.73	ChemAxon
pKa (Strongest Basic)	0.0061	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.24 m³·mol⁻¹	ChemAxon
Polarizability	17.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-5900000000-0197e550072c40b50073	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9600000000-d7aaece789b967cf6d49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01wf-7900000000-5e5fda28174d2f38e034	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-f851ecebf6b0ccd4c523	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2900000000-ecfabfb83bc9e1fffb60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7900000000-8ef68b55534d7b1f386e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-14e8ca9900631824076f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-30ab82031d48f66f45ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-4573dc12b33bcf32df76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9100000000-bd289a1212000ffd9b33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-d67a78722745354ea944	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-5900000000-baad3afa942ca9d191c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9200000000-81ded39078c95bc7eeba	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013859

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Aleksa K, Matsell D, Krausz K, Gelboin H, Ito S, Koren G: Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr Nephrol. 2005 Jul;20(7):872-85. doi: 10.1007/s00467-004-1807-3. Epub 2005 May 4.

2-Dechloroethylifosfamide (CHEM021966)

Structure for CHEM021966: 2-Dechloroethylifosfamide