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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 19:13:53 UTC

Update Date

2019-07-23 07:14:52 UTC

HMDB ID

HMDB0060691

Secondary Accession Numbers

HMDB60691

Metabolite Identification

Common Name

Isophosphamide mustard

Description

Isophosphamide mustard, also known as palifosfamide-tris or ifosforamide mustard, belongs to the class of organic compounds known as organic phosphoric acid diamides. These are organophosphorus compounds with the general formula RNP(R2)(O)=O (R=alkyl, aryl; R2 = amine group). Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. Isophosphamide mustard is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, isophosphamide mustard is involved in ifosfamide metabolism pathway. Isophosphamide mustard is a metabolite of ifosfamide. It is sometimes abbreviated 'IFO'.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ifosfamide mustard	Kegg
NN'-Bis-(2-chloroethyl)phosphoric acid	HMDB
Zio-201isophosphamide mustard	HMDB
NN'-Bis-(2-chloroethyl)phosphate	HMDB
Palifosfamide-tris	HMDB
Isophosphoramide mustard	HMDB
Ifosforamide mustard	HMDB
IPAM	HMDB
N,N'-di-(2-chloroethyl)phosphorodiamidic acid	HMDB
Iphosphoramide mustard	HMDB
Isophosphamide mustard	MeSH
Palifosfamide	MeSH

Chemical Formula

C₄H₁₁Cl₂N₂O₂P

Average Molecular Weight

221.022

Monoisotopic Molecular Weight

219.993519532

IUPAC Name

bis[(2-chloroethyl)amino]phosphinic acid

Traditional Name

IPAM

CAS Registry Number

Not Available

SMILES

OP(=O)(NCCCl)NCCCl

InChI Identifier

InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)

InChI Key

BKCJZNIZRWYHBN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic phosphoric acid diamides. These are organophosphorus compounds with the general formula RNP(R2)(O)=O (R=alkyl, aryl; R2 = amine group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Organic phosphoramides

Direct Parent

Organic phosphoric acid diamides

Alternative Parents

Substituents

Organic phosphoric acid diamide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphorodiamide (CHEBI:80566 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060691)

Organ

Liver (HMDB: HMDB0060691)
Kidney (HMDB: HMDB0060691)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060691)

Source

Endogenous

Endogenous (HMDB: HMDB0060691)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ifosfamide Action Pathway (PathBank: SMP0000448)

Metabolic pathway

Ifosfamide Metabolism Pathway (PathBank: SMP0000605)

Role

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	8.86 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	-0.39	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	5.43	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	46.2 m³·mol⁻¹	ChemAxon
Polarizability	19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	144.604	30932474
DeepCCS	[M-H]-	141.697	30932474
DeepCCS	[M-2H]-	177.774	30932474
DeepCCS	[M+Na]+	153.31	30932474
AllCCS	[M+H]+	144.2	32859911
AllCCS	[M+H-H2O]+	140.8	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	143.7	32859911
AllCCS	[M+Na-2H]-	145.9	32859911
AllCCS	[M+HCOO]-	148.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isophosphamide mustard	OP(=O)(NCCCl)NCCCl	2714.8	Standard polar	33892256
Isophosphamide mustard	OP(=O)(NCCCl)NCCCl	1632.2	Standard non polar	33892256
Isophosphamide mustard	OP(=O)(NCCCl)NCCCl	1771.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isophosphamide mustard,1TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)NCCCl	1845.8	Semi standard non polar	33892256
Isophosphamide mustard,1TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)NCCCl	1636.4	Standard non polar	33892256
Isophosphamide mustard,1TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)NCCCl	2558.1	Standard polar	33892256
Isophosphamide mustard,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	1890.2	Semi standard non polar	33892256
Isophosphamide mustard,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	1706.3	Standard non polar	33892256
Isophosphamide mustard,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	2703.0	Standard polar	33892256
Isophosphamide mustard,2TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	1844.0	Semi standard non polar	33892256
Isophosphamide mustard,2TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	1797.3	Standard non polar	33892256
Isophosphamide mustard,2TMS,isomer #1	C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2163.6	Standard polar	33892256
Isophosphamide mustard,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C	1902.5	Semi standard non polar	33892256
Isophosphamide mustard,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C	1876.9	Standard non polar	33892256
Isophosphamide mustard,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C	2307.8	Standard polar	33892256
Isophosphamide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	1949.8	Semi standard non polar	33892256
Isophosphamide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	1930.4	Standard non polar	33892256
Isophosphamide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2013.8	Standard polar	33892256
Isophosphamide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl	2092.2	Semi standard non polar	33892256
Isophosphamide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl	1883.3	Standard non polar	33892256
Isophosphamide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl	2619.5	Standard polar	33892256
Isophosphamide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	2147.9	Semi standard non polar	33892256
Isophosphamide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	1989.1	Standard non polar	33892256
Isophosphamide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl	2745.5	Standard polar	33892256
Isophosphamide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2340.4	Semi standard non polar	33892256
Isophosphamide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2225.4	Standard non polar	33892256
Isophosphamide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2343.2	Standard polar	33892256
Isophosphamide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C	2365.8	Semi standard non polar	33892256
Isophosphamide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C	2300.4	Standard non polar	33892256
Isophosphamide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C	2481.6	Standard polar	33892256
Isophosphamide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2586.6	Semi standard non polar	33892256
Isophosphamide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2456.9	Standard non polar	33892256
Isophosphamide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2332.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isophosphamide mustard GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g3-6910000000-53a3ebd8119a9d7c12be	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isophosphamide mustard 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 - Isophosphamide mustard 10V, Positive-QTOF	splash10-00e9-6090000000-28910cc262fc920160d6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Positive-QTOF	splash10-03ec-9300000000-53d6095d0fd353a7d7e9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Positive-QTOF	splash10-03di-9000000000-7cab03f69a1bc707e1a9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Negative-QTOF	splash10-066r-5890000000-e9d8316ea01b6f710a85	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Negative-QTOF	splash10-03di-9220000000-866eaf3137df6ba4df53	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Negative-QTOF	splash10-004l-9000000000-399fa980332aaff6d259	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Positive-QTOF	splash10-0006-0900000000-648a2ec89fc0f64efb3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Positive-QTOF	splash10-01po-7900000000-967a41020240370616d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Positive-QTOF	splash10-03di-9000000000-f1751c47be60b7d124c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Negative-QTOF	splash10-014i-0090000000-0e92f2f71d4e7fd82840	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Negative-QTOF	splash10-004i-9210000000-021eb4b0e46c0edb4d81	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Negative-QTOF	splash10-004i-9000000000-44e5373925906348e041	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

C16559

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100427

PDB ID

Not Available

ChEBI ID

80566

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

Not Available

Showing metabocard for Isophosphamide mustard (HMDB0060691)

MOL for HMDB0060691 (Isophosphamide mustard)

3D MOL for HMDB0060691 (Isophosphamide mustard)

3D SDF for HMDB0060691 (Isophosphamide mustard)

3D-SDF for HMDB0060691 (Isophosphamide mustard)

PDB for HMDB0060691 (Isophosphamide mustard)

3D PDB for HMDB0060691 (Isophosphamide mustard)

SMILES for HMDB0060691 (Isophosphamide mustard)

INCHI for HMDB0060691 (Isophosphamide mustard)

Structure for HMDB0060691 (Isophosphamide mustard)

3D Structure for HMDB0060691 (Isophosphamide mustard)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra