Human Metabolome Database: Showing metabocard for Phosphoramide mustard (HMDB0060689)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2013-06-18 19:13:46 UTC

Update Date

2017-12-20 20:30:54 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 SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

This compound belongs to the class of organic compounds known as nitrogen mustard compounds. These 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

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Organ and components:

Process

Naturally occurring process:

Physical Properties

State

Not Available

Experimental 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

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9800000000-9972fd7a6e0c1422d231	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0290000000-25ff81c3728c97ca3c79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gvo-6890000000-829ce130e33191766175	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-9200000000-9bb5c816df0fb9b6d5c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2920000000-c8f586cd1a182aa03251	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-9110000000-3c16b08c4682a336aba3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056s-9200000000-320fe847d1c97b4d2d64	View in MoNA