Metabolite Carboxyphosphamide

Name

Carboxyphosphamide

Description

n contrast to previous adult studies on urinary metabolites, plasma carboxyphosphamide concentrations did not support the existence of polymorphic metabolism. Plasma concentrations of dechlorethylcyclophosphamide and carboxyphosphamide were correlated in individual patients, suggesting that the activity of both aldehyde dehydrogenase and cytochrome P450 enzyme(s) determine carboxyphosphamide production in vivo. (PMID: 7850793 ) Detoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. (PMID: 9394035 ) A key finding was the detection of a metabolite, most likely carboxyphosphamide, that is formed only by cytosols from cells expressing either class 3 or class 1 ALDH. (PMID: 8662659 )

Structure

Similar Structures

Synonyms

Not Available

UNII

DP4677AX41

CAS number

Not Available

Weight

Average: 293.085
Monoisotopic: 292.014648904

Chemical Formula

C₇H₁₅Cl₂N₂O₄P

InChI Key

QLAKAJLYYGOZQL-UHFFFAOYSA-N

InChI

InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13)

IUPAC Name

3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid

SMILES

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

Reactions

Cyclophosphamide

4-Hydroxycyclophosphamide
- 4-Hydroxycyclophosphamide
  
  4-Ketocyclophosphamide
- 4-Hydroxycyclophosphamide
  
  Aldophosphamide

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-6950000000-ed4ce5a2a1fd50084a35
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a6u-0190000000-f03aba2afa8ffc2974cd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-2090000000-13bafd34ea0537c7d224
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0920000000-96ce618237ecb4118d83
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-4790000000-87ef3425bcc22f582a1e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052u-4900000000-420cd00c423e14dd3f02
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-9000000000-e5a6ecffe0bde085a0e6

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	153.9047179	predicted	DarkChem Lite v0.1.0
[M-H]-	158.9375179	predicted	DarkChem Lite v0.1.0
[M-H]-	152.04263	predicted	DeepCCS 1.0 (2019)
[M+H]+	154.6814179	predicted	DarkChem Lite v0.1.0
[M+H]+	158.4482179	predicted	DarkChem Lite v0.1.0
[M+H]+	154.40063	predicted	DeepCCS 1.0 (2019)
[M+Na]+	153.7679179	predicted	DarkChem Lite v0.1.0
[M+Na]+	158.2243179	predicted	DarkChem Lite v0.1.0
[M+Na]+	160.82947	predicted	DeepCCS 1.0 (2019)

External Links

Human Metabolome Database: HMDB0060449
KEGG Compound: C07646
ChemSpider: 29229
ChEBI: 3410
ChEMBL: CHEMBL3544547
Wikipedia: Carboxycyclophosphamide

Predicted Properties

Property	Value	Source
Water Solubility	13.6 mg/mL	ALOGPS
logP	0.37	ALOGPS
logP	-0.3	Chemaxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.49	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	92.86 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	61.47 m³·mol^-1	Chemaxon
Polarizability	25.75 Å³	Chemaxon
Number of Rings	0	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite Carboxyphosphamide

Structure for Carboxyphosphamide

Collision Cross Sections (CCS)