Reaction1819
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040518/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008616/Stoichiometry/1.0
right: 4-Ketoifosfamide
spontaneous: false
left: 4-Hydroxyifosfamide
name: 4-Hydroxyifosfamide → 4-Ketoifosfamide
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C009594 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008616 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: 4-Hydroxyifosfamide
right: NADP
spontaneous: false
EC number: 1.14.14.1
left: Ifosfamide
left: Oxygen
left: NADPH
left: Hydrogen Ion
name: Hydrogen Ion + Ifosfamide + NADPH + Oxygen → 4-Hydroxyifosfamide + NADP + Water
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 17215925
type: UnificationXref
id: 17215925
db: ChemSpider

Reference/UniProt P00352
type: UnificationXref
id: P00352
db: UniProt

4-Ketoifosfamide
type: SmallMolecule
entity reference: 4-Ketoifosfamide

Reference/ChemSpider 937
type: UnificationXref
id: 937
db: ChemSpider

ChemicalStructure/PW C008616
type: ChemicalStructure
structure format: SMILES
structure data: OC1CCOP(=O)(NCCCl)N1CCCl

Reference/PubChem-compound 439153
type: UnificationXref
id: 439153
db: PubChem-compound

ChemicalStructure/PW C001420
type: ChemicalStructure
structure format: SMILES
structure data: O

Cytochrome P450 3A4
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 3A4

Isophosphamide mustard
type: SmallMolecule
cellular location: Cytosol
entity reference: Isophosphamide mustard

Acrolein
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0041822
xref: Reference/CAS 107-02-8
xref: Reference/ChEBI CHEBI 15368
xref: Reference/KEGG Compound C01471
xref: Reference/ChemSpider 7559
xref: Reference/PubChem-compound 7847
chemical formula: C3H4O
molecular weight: 56.026215
structure: ChemicalStructure/PW C022605

Cytochrome P450 3A4
type: ProteinReference
xref: Reference/UniProt P08684
organism: BiologicalState10

Cytochrome P450 2B6
type: ProteinReference
xref: Reference/UniProt P20813
organism: BiologicalState10

NADPH
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: NADPH

Cytochrome P450 3A5
type: ProteinReference
xref: Reference/UniProt P20815
organism: BiologicalState10

Reference/ChemSpider 110614
type: UnificationXref
id: 110614
db: ChemSpider

Reference/CAS 53459-52-2
type: UnificationXref
id: 53459-52-2
db: CAS

Acrolein
type: SmallMolecule
cellular location: Cytosol
entity reference: Acrolein

Protein/194 Cytoplasm/Stoichiometry/4.0
type: Stoichiometry
physical entity: Retinal dehydrogenase 1
stoichiometric coefficient: 4.0

Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

Water
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Water

Reference/CAS 120144-70-9
type: UnificationXref
id: 120144-70-9
db: CAS

Reference/ChEBI CHEBI 15846
type: UnificationXref
id: CHEBI:15846
db: ChEBI

Reference/HMDB HMDB0013861
type: UnificationXref
id: HMDB0013861
db: HMDB

Reference/PubChem-compound 3690
type: UnificationXref
id: 3690
db: PubChem-compound

ChemicalStructure/PW C040488
type: ChemicalStructure
structure format: SMILES
structure data: ClCCNP(=O)(NCCCl)OCCC=O

Reference/CAS 53-59-8
type: UnificationXref
id: 53-59-8
db: CAS

Cytochrome P450 2A6
type: ProteinReference
xref: Reference/UniProt P11509
organism: BiologicalState10

Reference/BRENDA TISSUE ONTOLOGY BTO 0000759
type: UnificationXref
id: BTO:0000759
db: BRENDA TISSUE ONTOLOGY

Compound/PW C008616 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Hydroxyifosfamide
stoichiometric coefficient: 1.0

Reference/ChemSpider 3562
type: UnificationXref
id: 3562
db: ChemSpider

Reference/PubChem-compound 1038
type: UnificationXref
id: 1038
db: PubChem-compound

Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
stoichiometric coefficient: 1.0

Cytochrome P450 2C8
type: ProteinReference
xref: Reference/UniProt P10632
organism: BiologicalState10

Reference/ChEBI CHEBI 16474
type: UnificationXref
id: CHEBI:16474
db: ChEBI

Hydrogen Ion
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Hydrogen Ion

Reference/ChemSpider 952
type: UnificationXref
id: 952
db: ChemSpider

Reference/GENE ONTOLOGY GO 0005829
type: UnificationXref
id: GO:0005829
db: GENE ONTOLOGY

Aldehyde dehydrogenase, dimeric NADP-preferring
type: ProteinReference
xref: Reference/UniProt P30838
organism: Homo sapiens

Reference/ChemSpider 90740
type: UnificationXref
id: 90740
db: ChemSpider

ChemicalStructure/PW C040491
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CCOP(=O)(NCCCl)NCCCl

Reference/ChEBI CHEBI 16908
type: UnificationXref
id: CHEBI:16908
db: ChEBI

Reference/UniProt P11712
type: UnificationXref
id: P11712
db: UniProt

ChemicalStructure/PW C040497
type: ChemicalStructure
structure format: SMILES
structure data: OP(=O)(NCCCl)NCCCl

Reference/ChEBI CHEBI 18308
type: UnificationXref
id: CHEBI:18308
db: ChEBI

Compound/PW C040488 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Aldoifosfamide
stoichiometric coefficient: 1.0

4-Ketoifosfamide
type: SmallMoleculeReference
xref: Reference/PubChem-compound 99303
xref: Reference/HMDB HMDB0060690
xref: Reference/CAS 42436-20-4
xref: Reference/ChemSpider 89713
xref: Reference/KEGG Compound C16554
chemical formula: C7H13Cl2N2O3P
molecular weight: 274.0041
structure: ChemicalStructure/PW C040518

Cytochrome P450 2C9
type: ProteinReference
xref: Reference/UniProt P11712
organism: BiologicalState10

Reference/ChemSpider 1010
type: UnificationXref
id: 1010
db: ChemSpider

ReactionCatalysis1599
type: Catalysis
controller: Cytochrome P450 3A4
controlled: 1.14.14.1
control type: ACTIVATION

Reference/CAS 3778-73-2
type: UnificationXref
id: 3778-73-2
db: CAS

Transport13641
type: Transport
participant stoichiometry: Compound/PW C040497 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040497 Nucleus/Stoichiometry/1.0
right: Isophosphamide mustard
spontaneous: false
left: Isophosphamide mustard
name: Isophosphamide mustard (→) Transport: Homo sapiens, Cell, Cytosol to Homo sapiens, Cell, Nucleus
conversion direction: LEFT_TO_RIGHT

NADPH
type: SmallMoleculeReference
xref: Reference/CAS 53-57-6
xref: Reference/HMDB HMDB0000221
xref: Reference/PubChem-compound 22833512
xref: Reference/BioCyc NADPH
xref: Reference/ChemSpider 17215925
xref: Reference/KEGG Compound C00005
xref: Reference/ChEBI CHEBI 16474
chemical formula: C21H30N7O17P3
molecular weight: 745.0911
structure: ChemicalStructure/PW C000146

Reaction1820
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040488 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008616 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Aldoifosfamide
spontaneous: false
left: 4-Hydroxyifosfamide
name: 4-Hydroxyifosfamide ↔ Aldoifosfamide
conversion direction: REVERSIBLE

NADP
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00006
xref: Reference/CAS 53-59-8
xref: Reference/BioCyc NAD(P)
xref: Reference/HMDB HMDB0000217
xref: Reference/ChEBI CHEBI 18009
xref: Reference/PubChem-compound 5886
xref: Reference/ChemSpider 5675
chemical formula: C21H28N7O17P3
molecular weight: 743.07544
structure: ChemicalStructure/PW C000143

ReactionCatalysis1595
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.14.1
control type: ACTIVATION

ReactionCatalysis1594
type: Catalysis
controller: Cytochrome P450 2C8
controlled: 1.14.14.1
control type: ACTIVATION

ReactionCatalysis1597
type: Catalysis
controller: Cytochrome P450 2B6
controlled: 1.14.14.1
control type: ACTIVATION

Aldoifosfamide
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Aldoifosfamide

Reference/BioCyc NADPH
type: UnificationXref
id: NADPH
db: BioCyc

Compound/PW C040034 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 1.0

Aldoifosfamide
type: SmallMoleculeReference
xref: Reference/CAS 120144-70-9
xref: Reference/ChemSpider 164793
xref: Reference/PubChem-compound 189733
xref: Reference/HMDB HMDB0060588
xref: Reference/KEGG Compound C16556
chemical formula: C7H15Cl2N2O3P
molecular weight: 276.01974
structure: ChemicalStructure/PW C040488

Retinal dehydrogenase 1
type: Complex
component stoichiometry: Protein/194 Cytoplasm/Stoichiometry/4.0
cellular location: Cytoplasm
component: Retinal dehydrogenase 1

Transport13637
type: Transport
participant stoichiometry: Compound/PW C040488 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040488 Extracellular Space/Stoichiometry/1.0
right: Aldoifosfamide
spontaneous: false
left: Aldoifosfamide
name: Aldoifosfamide (→) Transport: Homo sapiens, Liver, Cell, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

Cytosol
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005829

Reference/BioCyc CPD-6641
type: UnificationXref
id: CPD-6641
db: BioCyc

Transport13638
type: Transport
participant stoichiometry: Compound/PW C040488 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040488 Cytosol/Stoichiometry/1.0
right: Aldoifosfamide
spontaneous: false
left: Aldoifosfamide
name: Aldoifosfamide (→) Transport: Homo sapiens, Blood Vessel, Cell, Extracellular Space to Homo sapiens, Cell, Cytosol
conversion direction: LEFT_TO_RIGHT

Reference/PubChem-compound 308171
type: UnificationXref
id: 308171
db: PubChem-compound

Cytochrome P450 3A5
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 3A5

Reference/CAS 58-68-4
type: UnificationXref
id: 58-68-4
db: CAS

Reference/HMDB HMDB0000217
type: UnificationXref
id: HMDB0000217
db: HMDB

Carboxyifosfamide
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0060692
xref: Reference/KEGG Compound C16557
xref: Reference/ChemSpider 110614
xref: Reference/CAS 53459-52-2
xref: Reference/PubChem-compound 124143
chemical formula: C7H15Cl2N2O4P
molecular weight: 292.01465
structure: ChemicalStructure/PW C040491

Reference/KEGG Compound C00007
type: UnificationXref
id: C00007
db: KEGG Compound

Oxygen
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Oxygen

Isophosphamide mustard
type: SmallMoleculeReference
xref: Reference/CAS 31645-39-3
xref: Reference/HMDB HMDB0060691
xref: Reference/ChemSpider 90740
xref: Reference/KEGG Compound C16559
xref: Reference/PubChem-compound 100427
chemical formula: C4H11Cl2N2O2P
molecular weight: 219.99352
structure: ChemicalStructure/PW C040497

Reference/KEGG Compound C00006
type: UnificationXref
id: C00006
db: KEGG Compound

Carboxyifosfamide
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Carboxyifosfamide

Reference/ChEBI CHEBI 18009
type: UnificationXref
id: CHEBI:18009
db: ChEBI

Compound/PW C040488 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Aldoifosfamide
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00001
type: UnificationXref
id: C00001
db: KEGG Compound

Reference/ChemSpider 89713
type: UnificationXref
id: 89713
db: ChemSpider

Reference/KEGG Compound C00005
type: UnificationXref
id: C00005
db: KEGG Compound

Reference/KEGG Compound C00004
type: UnificationXref
id: C00004
db: KEGG Compound

Reference/KEGG Compound C00003
type: UnificationXref
id: C00003
db: KEGG Compound

Liver
type: TissueVocabulary
xref: Reference/BRENDA TISSUE ONTOLOGY BTO 0000759

ChemicalStructure/PW C000143
type: ChemicalStructure
structure format: SMILES

Reference/HMDB HMDB0000221
type: UnificationXref
id: HMDB0000221
db: HMDB

ChemicalStructure/PW C000146
type: ChemicalStructure
structure format: SMILES

Reference/GENE ONTOLOGY GO 0005634
type: UnificationXref
id: GO:0005634
db: GENE ONTOLOGY

Reference/CAS 53-57-6
type: UnificationXref
id: 53-57-6
db: CAS

NAD
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 15846
xref: Reference/HMDB HMDB0000902
xref: Reference/CAS 53-84-9
xref: Reference/KEGG Compound C00003
xref: Reference/PubChem-compound 5893
xref: Reference/BioCyc NAD
xref: Reference/ChemSpider 5682
chemical formula: C21H27N7O14P2
molecular weight: 663.10913
structure: ChemicalStructure/PW C000721

Reference/HMDB HMDB0000902
type: UnificationXref
id: HMDB0000902
db: HMDB

Isophosphamide mustard
type: SmallMolecule
cellular location: Nucleus
entity reference: Isophosphamide mustard

Extracellular Space
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005615

Reference/ChemSpider 272429
type: UnificationXref
id: 272429
db: ChemSpider

Reference/BioCyc NAD(P)
type: UnificationXref
id: NAD(P)
db: BioCyc

Reference/KEGG Compound C01471
type: UnificationXref
id: C01471
db: KEGG Compound

NADH
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0001487
xref: Reference/CAS 58-68-4
xref: Reference/PubChem-compound 439153
xref: Reference/BioCyc NADH
xref: Reference/ChemSpider 388299
xref: Reference/KEGG Compound C00004
xref: Reference/ChEBI CHEBI 16908
chemical formula: C21H29N7O14P2
molecular weight: 665.12476
structure: ChemicalStructure/PW C001144

Reference/ChEBI CHEBI 5864
type: UnificationXref
id: CHEBI:5864
db: ChEBI

Compound/PW C001420 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Water
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0031647
type: UnificationXref
id: HMDB0031647
db: HMDB

1.2.1.36
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040488 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000721 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040491 Cytoplasm/Stoichiometry/1.0
right: Hydrogen Ion
right: Carboxyifosfamide
right: NADH
spontaneous: false
EC number: 1.2.1.36
left: Aldoifosfamide
left: Water
left: NAD
name: Aldoifosfamide + NAD + Water → Carboxyifosfamide + Hydrogen Ion + NADH
conversion direction: LEFT_TO_RIGHT

Cytochrome P450 2B6
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2B6

Acrylic acid
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 18308
xref: Reference/HMDB HMDB0031647
xref: Reference/PubChem-compound 19966351
xref: Reference/ChemSpider 6333
xref: Reference/KEGG Compound C00511
xref: Reference/CAS 9003-01-4
chemical formula: C3H4O2
molecular weight: 72.021126
structure: ChemicalStructure/PW C012827

Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

Hydrogen Ion
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00080
xref: Reference/ChEBI CHEBI 15378
xref: Reference/HMDB HMDB0059597
xref: Reference/PubChem-compound 1038
xref: Reference/ChemSpider 1010
chemical formula: H
molecular weight: 1.007825
structure: ChemicalStructure/PW C040034

Reference/SMPDB SMP0124478
type: UnificationXref
id: SMP0124478
db: SMPDB

Retinal dehydrogenase 1
type: Protein
cellular location: Cytoplasm
entity reference: Retinal dehydrogenase 1

Compound/PW C008616/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Hydroxyifosfamide
stoichiometric coefficient: 1.0

Reference/CAS 53-84-9
type: UnificationXref
id: 53-84-9
db: CAS

Reference/GENE ONTOLOGY GO 0005615
type: UnificationXref
id: GO:0005615
db: GENE ONTOLOGY

Cytochrome P450 2A6
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2A6

Reference/GENE ONTOLOGY GO 0005737
type: UnificationXref
id: GO:0005737
db: GENE ONTOLOGY

1.2.1.36
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000721 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C022605 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C012827 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Cytoplasm/Stoichiometry/1.0
right: Hydrogen Ion
right: Acrylic acid
right: NADH
spontaneous: false
EC number: 1.2.1.36
left: Acrolein
left: Water
left: NAD
name: Acrolein + NAD + Water → Acrylic acid + Hydrogen Ion + NADH
conversion direction: LEFT_TO_RIGHT

Reference/CAS 107-02-8
type: UnificationXref
id: 107-02-8
db: CAS

Aldoifosfamide
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Aldoifosfamide

Endoplasmic Reticulum Membrane
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005789

NADH
type: SmallMolecule
cellular location: Cytoplasm
entity reference: NADH

ChemicalStructure/PW C000721
type: ChemicalStructure
structure format: SMILES

4-Hydroxyifosfamide
type: SmallMolecule
entity reference: 4-Hydroxyifosfamide

Reference/ChemSpider 5682
type: UnificationXref
id: 5682
db: ChemSpider

ChemicalStructure/PW C001144
type: ChemicalStructure
structure format: SMILES

ReactionCatalysis1600
type: Catalysis
controller: Cytochrome P450 3A5
controlled: 1.14.14.1
control type: ACTIVATION

ChemicalStructure/PW C012827
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)C=C

Compound/PW C040491 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Carboxyifosfamide
stoichiometric coefficient: 1.0

ChemicalStructure/PW C040518
type: ChemicalStructure
structure format: SMILES
structure data: ClCCNP1(=O)OCCC(=O)N1CCCl

Reference/ChemSpider 5675
type: UnificationXref
id: 5675
db: ChemSpider

Reference/UniProt P30838
type: UnificationXref
id: P30838
db: UniProt

Cytoplasm
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005737

Compound/PW C001144 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADH
stoichiometric coefficient: 1.0

Compound/PW C040497 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Isophosphamide mustard
stoichiometric coefficient: 1.0

Cytochrome P450 2C8
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2C8

Compound/PW C009594 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Ifosfamide
stoichiometric coefficient: 1.0

Homo sapiens
type: BioSource
xref: Reference/TAXONOMY 9606

Reference/CAS 7732-18-5
type: UnificationXref
id: 7732-18-5
db: CAS

Reference/ChemSpider 388299
type: UnificationXref
id: 388299
db: ChemSpider

Reference/PubChem-compound 189733
type: UnificationXref
id: 189733
db: PubChem-compound

Compound/PW C001420 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Water
stoichiometric coefficient: 1.0

Water
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Water

Acrolein
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Acrolein

Reference/HMDB HMDB0001487
type: UnificationXref
id: HMDB0001487
db: HMDB

Cytochrome P450 2C9
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2C9

Hydrogen Ion
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Hydrogen Ion

Oxygen
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0001377
xref: Reference/ChemSpider 952
xref: Reference/KEGG Compound C00007
xref: Reference/ChEBI CHEBI 15379
xref: Reference/PubChem-compound 977
xref: Reference/BioCyc CPD-6641
xref: Reference/CAS 7782-44-7
chemical formula: O2
molecular weight: 31.98983
structure: ChemicalStructure/PW C001065

ReactionCatalysis1743
type: Catalysis
controller: Cytochrome P450 2A6
controlled: 1.14.14.1
control type: ACTIVATION

Reference/GENE ONTOLOGY GO 0005789
type: UnificationXref
id: GO:0005789
db: GENE ONTOLOGY

Reference/CAS 67292-64-2
type: UnificationXref
id: 67292-64-2
db: CAS

Ifosfamide Alkylating Agent Action Pathway
type: Pathway
pathway order: PathwayEnzymeReaction/2498971
pathway order: PathwayTransport/2498977
pathway order: PathwayEnzymeReaction/2498950
pathway order: PathwayEnzymeReaction/2498951
pathway order: PathwayEnzymeReaction/2498952
pathway order: PathwayEnzymeReaction/2498974
pathway order: PathwayEnzymeReaction/2498957
pathway order: PathwayEnzymeReaction/2498958
pathway order: PathwayEnzymeReaction/2498949
pathway order: PathwayEnzymeReaction/2498953
pathway order: PathwayTransport/2498973
pathway order: PathwayEnzymeReaction/2498954
pathway order: PathwayEnzymeReaction/2498955
pathway order: PathwayEnzymeReaction/2498956
pathway order: PathwayTransport/2498972
pathway component: Reaction1819
pathway component: 1.14.14.1
pathway component: Transport13637
pathway component: Transport13638
pathway component: Reaction217635
pathway component: ReactionCatalysis1599
pathway component: ReactionCatalysis1600
pathway component: ReactionCatalysis1743
pathway component: Transport13641
pathway component: 1.2.1.36
pathway component: Reaction1820
pathway component: ReactionCatalysis1595
pathway component: ReactionCatalysis1485
pathway component: ReactionCatalysis1496
pathway component: ReactionCatalysis1594
pathway component: ReactionCatalysis1597
pathway component: ReactionCatalysis1486
xref: Reference/SMPDB SMP0124478
xref: Reference/PathWhiz PW125958
organism: Homo sapiens

BiologicalState10
type: BioSource
xref: Reference/TAXONOMY 9606
name: Homo sapiens, Liver
tissue: Liver

ChemicalStructure/PW C022605
type: ChemicalStructure
structure format: SMILES
structure data: C=CC=O

Reference/CAS 7782-44-7
type: UnificationXref
id: 7782-44-7
db: CAS

Reference/HMDB HMDB0001377
type: UnificationXref
id: HMDB0001377
db: HMDB

Compound/PW C040488 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Aldoifosfamide
stoichiometric coefficient: 1.0

Reference/UniProt P20815
type: UnificationXref
id: P20815
db: UniProt

Compound/PW C022605 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Acrolein
stoichiometric coefficient: 1.0

Ifosfamide
type: SmallMoleculeReference
xref: Reference/KEGG Compound C07047
xref: Reference/PubChem-compound 3690
xref: Reference/CAS 3778-73-2
xref: Reference/ChEBI CHEBI 5864
xref: Reference/ChemSpider 3562
xref: Reference/HMDB HMDB0015312
chemical formula: C7H15Cl2N2O2P
molecular weight: 260.0248
structure: ChemicalStructure/PW C009594

Reference/UniProt P20813
type: UnificationXref
id: P20813
db: UniProt

Reference/TAXONOMY 9606
type: UnificationXref
id: 9606
db: TAXONOMY

Reference/PubChem-compound 962
type: UnificationXref
id: 962
db: PubChem-compound

Reference/ChEBI CHEBI 15368
type: UnificationXref
id: CHEBI:15368
db: ChEBI

Reference/UniProt P10632
type: UnificationXref
id: P10632
db: UniProt

Reference/CAS 31645-39-3
type: UnificationXref
id: 31645-39-3
db: CAS

Reference/CAS 42436-20-4
type: UnificationXref
id: 42436-20-4
db: CAS

Compound/PW C040488 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Aldoifosfamide
stoichiometric coefficient: 1.0

Reference/PubChem-compound 19966351
type: UnificationXref
id: 19966351
db: PubChem-compound

Reference/ChemSpider 6333
type: UnificationXref
id: 6333
db: ChemSpider

Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00511
type: UnificationXref
id: C00511
db: KEGG Compound

Reference/PubChem-compound 5893
type: UnificationXref
id: 5893
db: PubChem-compound

Reference/CAS 9003-01-4
type: UnificationXref
id: 9003-01-4
db: CAS

Reference/KEGG Compound C00080
type: UnificationXref
id: C00080
db: KEGG Compound

ChemicalStructure/PW C001065
type: ChemicalStructure
structure format: SMILES
structure data: O=O

Reference/HMDB HMDB0002111
type: UnificationXref
id: HMDB0002111
db: HMDB

ReactionCatalysis1485
type: Catalysis
controller: Retinal dehydrogenase 1
controlled: 1.2.1.36
control type: ACTIVATION

ReactionCatalysis1486
type: Catalysis
controller: Aldehyde dehydrogenase, dimeric NADP-preferring
controlled: 1.2.1.36
control type: ACTIVATION

Reference/HMDB HMDB0060588
type: UnificationXref
id: HMDB0060588
db: HMDB

Reference/ChEBI CHEBI 15377
type: UnificationXref
id: CHEBI:15377
db: ChEBI

Reference/ChEBI CHEBI 15379
type: UnificationXref
id: CHEBI:15379
db: ChEBI

Reference/ChEBI CHEBI 15378
type: UnificationXref
id: CHEBI:15378
db: ChEBI

ChemicalStructure/PW C040034
type: ChemicalStructure
structure format: SMILES
structure data: [H+]

Reference/UniProt P08684
type: UnificationXref
id: P08684
db: UniProt

Compound/PW C040497 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Isophosphamide mustard
stoichiometric coefficient: 1.0

Compound/PW C022605 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Acrolein
stoichiometric coefficient: 1.0

4-Hydroxyifosfamide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: 4-Hydroxyifosfamide

Reference/PubChem-compound 5886
type: UnificationXref
id: 5886
db: PubChem-compound

Reaction217635
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040497 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040488 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C022605 Cytosol/Stoichiometry/1.0
right: Acrolein
right: Isophosphamide mustard
spontaneous: false
left: Aldoifosfamide
name: Aldoifosfamide → Acrolein + Isophosphamide mustard
conversion direction: LEFT_TO_RIGHT

Reference/HMDB HMDB0015312
type: UnificationXref
id: HMDB0015312
db: HMDB

Reference/KEGG Compound C07047
type: UnificationXref
id: C07047
db: KEGG Compound

Compound/PW C040518/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Ketoifosfamide
stoichiometric coefficient: 1.0

Ifosfamide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Ifosfamide

Aldehyde dehydrogenase, dimeric NADP-preferring
type: Protein
cellular location: Cytoplasm
entity reference: Aldehyde dehydrogenase, dimeric NADP-preferring

Retinal dehydrogenase 1
type: ProteinReference
xref: Reference/UniProt P00352
organism: Homo sapiens

Reference/PubChem-compound 100427
type: UnificationXref
id: 100427
db: PubChem-compound

ReactionCatalysis1496
type: Catalysis
controller: Retinal dehydrogenase 1
controlled: 1.2.1.36
control type: ACTIVATION

ChemicalStructure/PW C009594
type: ChemicalStructure
structure format: SMILES
structure data: ClCCNP1(=O)OCCCN1CCCl

Reference/HMDB HMDB0060692
type: UnificationXref
id: HMDB0060692
db: HMDB

Reference/HMDB HMDB0060691
type: UnificationXref
id: HMDB0060691
db: HMDB

Reference/HMDB HMDB0060690
type: UnificationXref
id: HMDB0060690
db: HMDB

Compound/PW C000721 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: NAD
stoichiometric coefficient: 1.0

Compound/PW C012827 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Acrylic acid
stoichiometric coefficient: 1.0

Reference/ChemSpider 164793
type: UnificationXref
id: 164793
db: ChemSpider

Reference/UniProt P11509
type: UnificationXref
id: P11509
db: UniProt

Reference/PubChem-compound 124143
type: UnificationXref
id: 124143
db: PubChem-compound

Reference/PubChem-compound 99303
type: UnificationXref
id: 99303
db: PubChem-compound

Reference/PubChem-compound 22833512
type: UnificationXref
id: 22833512
db: PubChem-compound

4-Hydroxyifosfamide
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0013861
xref: Reference/ChemSpider 272429
xref: Reference/KEGG Compound C16553
xref: Reference/PubChem-compound 308171
xref: Reference/CAS 67292-64-2
chemical formula: C7H15Cl2N2O3P
molecular weight: 276.01974
structure: ChemicalStructure/PW C008616

Water
type: SmallMoleculeReference
xref: Reference/PubChem-compound 962
xref: Reference/ChEBI CHEBI 15377
xref: Reference/KEGG Compound C00001
xref: Reference/ChemSpider 937
xref: Reference/HMDB HMDB0002111
xref: Reference/CAS 7732-18-5
chemical formula: H2O
molecular weight: 18.010565
structure: ChemicalStructure/PW C001420

Reference/KEGG Compound C16557
type: UnificationXref
id: C16557
db: KEGG Compound

Reference/KEGG Compound C16559
type: UnificationXref
id: C16559
db: KEGG Compound

Reference/KEGG Compound C16553
type: UnificationXref
id: C16553
db: KEGG Compound

Reference/BioCyc NADH
type: UnificationXref
id: NADH
db: BioCyc

Reference/KEGG Compound C16554
type: UnificationXref
id: C16554
db: KEGG Compound

Nucleus
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005634

NADP
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: NADP

Reference/BioCyc NAD
type: UnificationXref
id: NAD
db: BioCyc

Reference/KEGG Compound C16556
type: UnificationXref
id: C16556
db: KEGG Compound

Reference/HMDB HMDB0041822
type: UnificationXref
id: HMDB0041822
db: HMDB

Reference/PubChem-compound 977
type: UnificationXref
id: 977
db: PubChem-compound

Reference/HMDB HMDB0059597
type: UnificationXref
id: HMDB0059597
db: HMDB

Acrylic acid
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Acrylic acid

Reference/ChemSpider 7559
type: UnificationXref
id: 7559
db: ChemSpider

Reference/PubChem-compound 7847
type: UnificationXref
id: 7847
db: PubChem-compound

Reference/PathWhiz PW125958
type: UnificationXref
id: PW125958
db: PathWhiz

Aldoifosfamide
type: SmallMolecule
cellular location: Cytosol
entity reference: Aldoifosfamide

NAD
type: SmallMolecule
cellular location: Cytoplasm
entity reference: NAD

Aldoifosfamide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Aldoifosfamide