ChemFOnt: Showing chemical card for 4-Hydroxyifosfamide (CFc000008614)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:28 UTC

Chemfont ID

CFc000008614

Molecule Identification

Common Name

4-Hydroxyifosfamide

Definition

4-Hydroxyifosfamide is the active metabolite of the bifunctional alkylating cytostatic drug known as ifosfamide. 4-Hydroxyifosfamide 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. 4-Hydroxyifosfamide is very unstable in plasma and a stabilization procedure by adding citric acid has been developed (PMID: 9172103 ). 4-Hydroxyifosfamide is known to pass through the blood-brain barrier, and can reach cerebrospinal fluid concentrations that are almost as high as plasma concentrations (PMID: 9677448 ). 4-Hydroxyifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-ifosfamide	HMDB
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinan-4-ol 2-oxide	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₃P

Average Molecular Weight

277.085

Monoisotopic Molecular Weight

276.019734282

IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

4-hydroxyifosfamide

CAS Registry Number

67292-64-2

SMILES

OC1CCOP(=O)(NCCCl)N1CCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)

InChI Key

JHUJMHKRHQPBRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazaphosphinanes

Sub Class

Isofamides

Direct Parent

Isofamides

Alternative Parents

Substituents

Isofamide
Phosphoric monoester diamide
Organic phosphoric acid derivative
Organic phosphoric acid amide
Alkanolamine
Azacycle
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:80560 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013861)
Kidney (HMDB: HMDB0013861)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013861)

Source

Endogenous

Endogenous (HMDB: HMDB0013861)

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

Predicted Properties

Property	Value	Source
Water Solubility	22.2 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	-0.057	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.09 m³·mol⁻¹	ChemAxon
Polarizability	24.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013861

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

272429

KEGG Compound ID

C16553

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

308171

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-Hydroxyifosfamide (CFc000008614)

MOL for CFc000008614 (4-Hydroxyifosfamide)

3D MOL for CFc000008614 (4-Hydroxyifosfamide)

3D SDF for CFc000008614 (4-Hydroxyifosfamide)

3D-SDF for CFc000008614 (4-Hydroxyifosfamide)

PDB for CFc000008614 (4-Hydroxyifosfamide)

3D PDB for CFc000008614 (4-Hydroxyifosfamide)

SMILES for CFc000008614 (4-Hydroxyifosfamide)

INCHI for CFc000008614 (4-Hydroxyifosfamide)

Structure for CFc000008614 (4-Hydroxyifosfamide)

3D Structure for CFc000008614 (4-Hydroxyifosfamide)