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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:15 UTC

Update Date

2023-02-21 17:18:05 UTC

HMDB ID

HMDB0013859

Secondary Accession Numbers

HMDB13859

Metabolite Identification

Common Name

2-Dechloroethylifosfamide

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

198.588

Monoisotopic Molecular Weight

198.032491857

IUPAC Name

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

Traditional Name

dechloroethylifosfamide

CAS Registry Number

53459-55-5

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 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.831	30932474
DeepCCS	[M-H]-	130.138	30932474
DeepCCS	[M-2H]-	166.033	30932474
DeepCCS	[M+Na]+	141.223	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.2	32859911
AllCCS	[M+NH4]+	145.0	32859911
AllCCS	[M+Na]+	146.1	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	141.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.71 minutes	32390414
Predicted by Siyang on May 30, 2022	9.346 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	199.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	597.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	284.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	282.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	449.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	657.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	180.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	771.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	238.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	508.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	358.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	110.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Dechloroethylifosfamide	NP1(=O)OCCCN1CCCl	2327.0	Standard polar	33892256
2-Dechloroethylifosfamide	NP1(=O)OCCCN1CCCl	1477.7	Standard non polar	33892256
2-Dechloroethylifosfamide	NP1(=O)OCCCN1CCCl	1736.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Dechloroethylifosfamide,1TMS,isomer #1	C[Si](C)(C)NP1(=O)OCCCN1CCCl	1719.3	Semi standard non polar	33892256
2-Dechloroethylifosfamide,1TMS,isomer #1	C[Si](C)(C)NP1(=O)OCCCN1CCCl	1644.2	Standard non polar	33892256
2-Dechloroethylifosfamide,1TMS,isomer #1	C[Si](C)(C)NP1(=O)OCCCN1CCCl	2509.5	Standard polar	33892256
2-Dechloroethylifosfamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl	1844.7	Semi standard non polar	33892256
2-Dechloroethylifosfamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl	1845.8	Standard non polar	33892256
2-Dechloroethylifosfamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl	2333.6	Standard polar	33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl	1985.6	Semi standard non polar	33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl	1910.9	Standard non polar	33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl	2686.5	Standard polar	33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl	2262.8	Semi standard non polar	33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl	2284.0	Standard non polar	33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl	2505.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-5900000000-0197e550072c40b50073	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Positive-QTOF	splash10-0006-9600000000-d7aaece789b967cf6d49	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Positive-QTOF	splash10-01wf-7900000000-5e5fda28174d2f38e034	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Positive-QTOF	splash10-0006-9100000000-f851ecebf6b0ccd4c523	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Negative-QTOF	splash10-000i-2900000000-ecfabfb83bc9e1fffb60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Negative-QTOF	splash10-014i-7900000000-8ef68b55534d7b1f386e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Negative-QTOF	splash10-004i-9000000000-14e8ca9900631824076f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Positive-QTOF	splash10-0002-0900000000-30ab82031d48f66f45ce	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Positive-QTOF	splash10-0002-0900000000-4573dc12b33bcf32df76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Positive-QTOF	splash10-03di-9100000000-bd289a1212000ffd9b33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Negative-QTOF	splash10-0002-0900000000-d67a78722745354ea944	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Negative-QTOF	splash10-0002-5900000000-baad3afa942ca9d191c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Negative-QTOF	splash10-01t9-9200000000-81ded39078c95bc7eeba	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Ifosfamide Action Pathway		Not Available
Ifosfamide Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106420

KEGG Compound ID

C16555

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119105

PDB ID

Not Available

ChEBI ID

80562

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:15875221 ]

Showing metabocard for 2-Dechloroethylifosfamide (HMDB0013859)

MOL for HMDB0013859 (2-Dechloroethylifosfamide)

3D MOL for HMDB0013859 (2-Dechloroethylifosfamide)

3D SDF for HMDB0013859 (2-Dechloroethylifosfamide)

3D-SDF for HMDB0013859 (2-Dechloroethylifosfamide)

PDB for HMDB0013859 (2-Dechloroethylifosfamide)

3D PDB for HMDB0013859 (2-Dechloroethylifosfamide)

SMILES for HMDB0013859 (2-Dechloroethylifosfamide)

INCHI for HMDB0013859 (2-Dechloroethylifosfamide)

Structure for HMDB0013859 (2-Dechloroethylifosfamide)

3D Structure for HMDB0013859 (2-Dechloroethylifosfamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra