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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 19:13:46 UTC

Update Date

2019-07-23 07:14:52 UTC

HMDB ID

HMDB0060689

Secondary Accession Numbers

HMDB60689

Metabolite Identification

Common Name

Phosphoramide mustard

Description

Phosphoramide mustard is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia)

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Friedman acid	ChEBI
Phosphamide mustard	ChEBI
Phosphorodiamidic mustard	ChEBI

Chemical Formula

C₄H₁₁Cl₂N₂O₂P

Average Molecular Weight

221.022

Monoisotopic Molecular Weight

219.993519532

IUPAC Name

amino[bis(2-chloroethyl)amino]phosphinic acid

Traditional Name

phosphoramide mustard

CAS Registry Number

Not Available

SMILES

NP(O)(=O)N(CCCl)CCCl

InChI Identifier

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

InChI Key

RJXQSIKBGKVNRT-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Organic phosphoric acid amide
Organic phosphoric acid diamide
Organic phosphoric acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nitrogen mustard (CHEBI:8163 )
phosphorodiamide (CHEBI:8163 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060689)

Organ

Liver (HMDB: HMDB0060689)
Kidney (HMDB: HMDB0060689)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060689)

Source

Endogenous

Endogenous (HMDB: HMDB0060689)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cyclophosphamide Action Pathway (PathBank: SMP0000447)

Metabolic pathway

Cyclophosphamide Metabolism Pathway (PathBank: SMP0000604)

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	26.3 g/L	ALOGPS
logP	0.3	ALOGPS
logP	-0.39	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	5.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	46.2 m³·mol⁻¹	ChemAxon
Polarizability	18.75 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]+	133.328	30932474
DeepCCS	[M-H]-	130.403	30932474
DeepCCS	[M-2H]-	166.629	30932474
DeepCCS	[M+Na]+	142.167	30932474
AllCCS	[M+H]+	144.5	32859911
AllCCS	[M+H-H2O]+	141.0	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.6	32859911
AllCCS	[M-H]-	141.8	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	146.5	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.	2.48 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8433 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	583.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	308.8 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	288.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	530.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	673.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	134.2 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	770.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	541.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	448.9 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	69.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphoramide mustard	NP(O)(=O)N(CCCl)CCCl	2520.4	Standard polar	33892256
Phosphoramide mustard	NP(O)(=O)N(CCCl)CCCl	1621.5	Standard non polar	33892256
Phosphoramide mustard	NP(O)(=O)N(CCCl)CCCl	1839.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphoramide mustard,1TMS,isomer #1	C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	1802.4	Semi standard non polar	33892256
Phosphoramide mustard,1TMS,isomer #1	C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	1704.8	Standard non polar	33892256
Phosphoramide mustard,1TMS,isomer #1	C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	3132.8	Standard polar	33892256
Phosphoramide mustard,1TMS,isomer #2	C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	1852.2	Semi standard non polar	33892256
Phosphoramide mustard,1TMS,isomer #2	C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	1718.6	Standard non polar	33892256
Phosphoramide mustard,1TMS,isomer #2	C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	2603.4	Standard polar	33892256
Phosphoramide mustard,2TMS,isomer #1	C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl	1846.8	Semi standard non polar	33892256
Phosphoramide mustard,2TMS,isomer #1	C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl	1806.7	Standard non polar	33892256
Phosphoramide mustard,2TMS,isomer #1	C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl	2106.6	Standard polar	33892256
Phosphoramide mustard,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl	1946.0	Semi standard non polar	33892256
Phosphoramide mustard,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl	1948.5	Standard non polar	33892256
Phosphoramide mustard,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl	2365.1	Standard polar	33892256
Phosphoramide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	1983.9	Semi standard non polar	33892256
Phosphoramide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	1999.3	Standard non polar	33892256
Phosphoramide mustard,3TMS,isomer #1	C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2041.9	Standard polar	33892256
Phosphoramide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	2058.3	Semi standard non polar	33892256
Phosphoramide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	1927.3	Standard non polar	33892256
Phosphoramide mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl	3265.9	Standard polar	33892256
Phosphoramide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	2125.4	Semi standard non polar	33892256
Phosphoramide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	1999.8	Standard non polar	33892256
Phosphoramide mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl	2660.4	Standard polar	33892256
Phosphoramide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2333.7	Semi standard non polar	33892256
Phosphoramide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2244.7	Standard non polar	33892256
Phosphoramide mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2319.5	Standard polar	33892256
Phosphoramide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl	2385.4	Semi standard non polar	33892256
Phosphoramide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl	2365.5	Standard non polar	33892256
Phosphoramide mustard,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl	2478.3	Standard polar	33892256
Phosphoramide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2618.9	Semi standard non polar	33892256
Phosphoramide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2551.4	Standard non polar	33892256
Phosphoramide mustard,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2319.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphoramide mustard GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9800000000-9972fd7a6e0c1422d231	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphoramide 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 - Phosphoramide mustard 10V, Positive-QTOF	splash10-00di-0290000000-25ff81c3728c97ca3c79	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Positive-QTOF	splash10-0gvo-6890000000-829ce130e33191766175	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Positive-QTOF	splash10-03fr-9200000000-9bb5c816df0fb9b6d5c8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Negative-QTOF	splash10-0a4i-2920000000-c8f586cd1a182aa03251	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Negative-QTOF	splash10-01t9-9110000000-3c16b08c4682a336aba3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Negative-QTOF	splash10-056s-9200000000-320fe847d1c97b4d2d64	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Positive-QTOF	splash10-00dr-0590000000-6100597620b7eda157e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Positive-QTOF	splash10-00dl-4970000000-76b0fe2ec1924e262a1a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Positive-QTOF	splash10-03di-9500000000-d00884a1a3f1a0ae5875	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Negative-QTOF	splash10-014i-1090000000-3898894eceeeafe3be0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Negative-QTOF	splash10-00pi-9450000000-dbf00c87965fd13c5766	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Negative-QTOF	splash10-03fr-9000000000-e4d1785ffbced7da2a23	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
Cyclophosphamide Action Pathway		Not Available
Cyclophosphamide 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

C07647

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

96356

PDB ID

Not Available

ChEBI ID

8163

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 Phosphoramide mustard (HMDB0060689)

MOL for HMDB0060689 (Phosphoramide mustard)

3D MOL for HMDB0060689 (Phosphoramide mustard)

3D SDF for HMDB0060689 (Phosphoramide mustard)

3D-SDF for HMDB0060689 (Phosphoramide mustard)

PDB for HMDB0060689 (Phosphoramide mustard)

3D PDB for HMDB0060689 (Phosphoramide mustard)

SMILES for HMDB0060689 (Phosphoramide mustard)

INCHI for HMDB0060689 (Phosphoramide mustard)

Structure for HMDB0060689 (Phosphoramide mustard)

3D Structure for HMDB0060689 (Phosphoramide mustard)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra