17215925
ChemSpider
7722-84-1
CAS
2.5.1.18
false
2.5.1.18
Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Water
LEFT_TO_RIGHT
Reaction1816
false
Carboxyphosphamide → Nornitrogen mustard
LEFT_TO_RIGHT
P00352
UniProt
Reaction1813
false
Cyclophosphamide + Oxygen + Water → 3-Dechloroethylifosfamide + Chloroacetaldehyde + Hydrogen peroxide
LEFT_TO_RIGHT
Reaction1814
false
4-Hydroxycyclophosphamide + NAD → 4-Ketocyclophosphamide + NADH
LEFT_TO_RIGHT
Nornitrogen mustard
937
ChemSpider
1.0
29229
ChemSpider
9533
PubChem-compound
HMDB0003125
HMDB
SMILES
[H]C(=O)CCl
SMILES
OC1CCOP(=O)(N1)N(CCCl)CCCl
439153
PubChem-compound
SMILES
ClCCNP1(=O)NCCCO1
SMILES
O
SMILES
ClCCN(CCCl)P1(=O)NCCCO1
SMILES
OO
Cytochrome P450 3A4
334-22-5
CAS
Cyclophosphamide
2907
PubChem-compound
ReactionCatalysis1563
ACTIVATION
SMILES
NP(=O)(OCCC=O)N(CCCl)CCCl
C3H4O
Acrolein
56.026215
35144-64-0
CAS
HMDB0013856
HMDB
SMILES
NP(O)(=O)[N]1(CCCl)CC1
SMILES
NP(O)(=O)N(CCCl)CCCl
4-Ketocyclophosphamide
391534
ChemSpider
Cytochrome P450 3A4
Cytochrome P450 2B6
NADPH
CHEBI:8163
ChEBI
4.0
Water
1.0
CHEBI:15846
ChEBI
Carboxyphosphamide
Chloroacetaldehyde
SMILES
NP(=O)(OCCC(O)=O)N(CCCl)CCCl
P33261
UniProt
1.0
53-59-8
CAS
Cytochrome P450 2A6
BTO:0000759
BRENDA TISSUE ONTOLOGY
50-18-0
CAS
C07647
KEGG Compound
1038
PubChem-compound
C07645
KEGG Compound
C00698
KEGG Compound
C07646
KEGG Compound
C07888
KEGG Compound
1.0
C07643
KEGG Compound
27046-19-1
CAS
CHEBI:16474
ChEBI
Hydrogen Ion
Cytochrome P450 2C8
HMDB0013860
HMDB
C07644
KEGG Compound
952
ChemSpider
107-20-0
CAS
Hydrogen peroxide
Aldehyde dehydrogenase, dimeric NADP-preferring
HMDB0013858
HMDB
CHEBI:1864
ChEBI
Cl
Chloride ion
34.968853
C11583
KEGG Compound
Transport259
false
Aldophosphamide (?) Transport: Homo sapiens, Liver, Cell, Cytoplasm to Homo sapiens, Cell, Cytoplasm
LEFT_TO_RIGHT
CHEBI:16908
ChEBI
P11712
UniProt
HMDB0060387
HMDB
CHEBI:18308
ChEBI
C7H13Cl2N2O3P
4-Ketocyclophosphamide
274.0041
CHEBI:16240
ChEBI
C17H30Cl2N5O8PS
4-Glutathionyl cyclophosphamide
565.09296
C4H9Cl2N
Nornitrogen mustard
141.0112
Cytochrome P450 2C9
1010
ChemSpider
33676
PubChem-compound
Cytochrome P450 2C19
ReactionCatalysis1470
ACTIVATION
C21H30N7O17P3
NADPH
745.0911
1.0
ReactionCatalysis1472
ACTIVATION
C21H29N7O17P3
NADP
744.08325
ReactionCatalysis1471
ACTIVATION
ReactionCatalysis1474
ACTIVATION
ReactionCatalysis1473
ACTIVATION
ReactionCatalysis1475
ACTIVATION
NADPH
BioCyc
1.0
Retinal dehydrogenase 1
P09488
UniProt
CHEBI:16856
ChEBI
124886
PubChem-compound
CPD-6641
BioCyc
4-Hydroxycyclophosphamide
58-68-4
CAS
SMILES
[Cl-]
Aldophosphamide
HMDB0000217
HMDB
Reaction1734
false
Cyclophosphamide + Hydrogen Ion + NADPH + Oxygen → 4-Hydroxycyclophosphamide + NADP + Water
LEFT_TO_RIGHT
1.0
CHEBI:27871
ChEBI
NADH
C00007
KEGG Compound
Oxygen
312
PubChem-compound
C00006
KEGG Compound
CHEBI:18009
ChEBI
C00001
KEGG Compound
C00005
KEGG Compound
C00004
KEGG Compound
C00003
KEGG Compound
Liver
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
HMDB0000221
HMDB
C10H17N3O6S
Glutathione
307.0838
99735
PubChem-compound
SMILES
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
2804
ChemSpider
53-57-6
CAS
C21H28N7O14P2
NAD
664.11694
HMDB0061263
HMDB
HMDB0000902
HMDB
C01471
KEGG Compound
C21H29N7O14P2
NADH
665.12476
NAD(P)
BioCyc
1.0
HMDB0031647
HMDB
1.0
C3H4O2
Acrylic acid
72.021126
Cytochrome P450 2B6
1.0
H
Hydrogen Ion
1.007825
1.0
Retinal dehydrogenase 1
1.2.1.36
false
1.2.1.36
Aldophosphamide + NAD + Water → Carboxyphosphamide + Hydrogen Ion + NADH
LEFT_TO_RIGHT
Reaction1747
false
Phosphoramide mustard → Chloride ion + Phosphoramide Aziridinium
LEFT_TO_RIGHT
53-84-9
CAS
C00027
KEGG Compound
ReactionCatalysis1557
ACTIVATION
HMDB0000125
HMDB
GO:0005737
GENE ONTOLOGY
Cytochrome P450 2A6
Reaction1745
false
Aldophosphamide → Phosphoramide mustard
LEFT_TO_RIGHT
33
PubChem-compound
1.2.1.5
false
1.2.1.5
Acrolein + NAD + Water → Acrylic acid + Hydrogen Ion + NADH
LEFT_TO_RIGHT
Reaction1741
false
Aldophosphamide → Acrolein
LEFT_TO_RIGHT
ReactionCatalysis1553
ACTIVATION
Reaction1740
false
4-Hydroxycyclophosphamide ↔ Aldophosphamide
REVERSIBLE
70-18-8
CAS
107-02-8
CAS
OXIDIZED-GLUTATHIONE
BioCyc
1.0
Endoplasmic Reticulum Membrane
NADH
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
CHEBI:37599
ChEBI
5682
ChemSpider
SMILES
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
22788-18-7
CAS
1.0
HYDROGEN-PEROXIDE
BioCyc
96908
ChemSpider
SMILES
OC(=O)C=C
HMDB0000492
HMDB
2.0
CHEBI:17996
ChEBI
1.0
SMILES
ClCCNCCCl
SMILES
NC(CCC(O)=NC(CSC1CCOP(=O)(N1)N(CCCl)CCCl)C(O)=NCC(O)=O)C(O)=O
5675
ChemSpider
SMILES
ClCCN(CCCl)P1(=O)NC(=O)CCO1
P30838
UniProt
16887-00-6
CAS
114861
PubChem-compound
763
ChemSpider
31515
PubChem-compound
C00051
KEGG Compound
NAD
Cytoplasm
1.0
Cyclophosphamide Action Pathway
HMDB0060433
HMDB
Cytochrome P450 2C8
784
PubChem-compound
Homo sapiens
7732-18-5
CAS
388299
ChemSpider
HMDB0014672
HMDB
1.0
Acrolein
HMDB0001487
HMDB
Water
Hydrogen Ion
1.0
Cytochrome P450 2C9
O2
Oxygen
31.98983
96356
PubChem-compound
GO:0005789
GENE ONTOLOGY
C7H15Cl2N2O3P
Aldophosphamide
276.01974
C4H11Cl2N2O2P
Phosphoramide mustard
219.99352
C4H11ClN2O2P
Phosphoramide Aziridinium
185.02467
BiologicalState10
Homo sapiens, Liver
306
ChemSpider
4-Hydroxycyclophosphamide
SMILES
C=CC=O
7782-44-7
CAS
90110
ChemSpider
HMDB0001377
HMDB
Cytochrome P450 2C19
1.0
102819
ChemSpider
Carboxyphosphamide
C7H15Cl2N2O4P
Carboxyphosphamide
292.01465
Glutathione S-transferase Mu 1
40277-05-2
CAS
P20813
UniProt
9606
TAXONOMY
962
PubChem-compound
CHEBI:15368
ChEBI
1.0
P10632
UniProt
1.0
SMP0000447
SMPDB
107744
PubChem-compound
19966351
PubChem-compound
6333
ChemSpider
C00511
KEGG Compound
1.0
4-Glutathionyl cyclophosphamide
5893
PubChem-compound
9003-01-4
CAS
C00080
KEGG Compound
SMILES
O=O
36761-83-8
CAS
1.0
HMDB0002111
HMDB
ReactionCatalysis1485
ACTIVATION
3-Dechloroethylifosfamide
Glutathione
ReactionCatalysis1486
ACTIVATION
CHEBI:15377
ChEBI
31058
ChemSpider
C16550
KEGG Compound
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
C16552
KEGG Compound
P08684
UniProt
5886
PubChem-compound
Glutathione S-transferase Mu 1
21106502
ChemSpider
1.0
Phosphoramide mustard
Aldehyde dehydrogenase, dimeric NADP-preferring
9160
ChemSpider
ReactionCatalysis1492
ACTIVATION
Retinal dehydrogenase 1
10159-53-2
CAS
ReactionCatalysis1493
ACTIVATION
111188
ChemSpider
CPD-4521
BioCyc
PW000248
PathWhiz
1.0
1.0
P11509
UniProt
443288
PubChem-compound
C06754
KEGG Compound
Chloride ion
C7H15Cl2N2O3P
4-Hydroxycyclophosphamide
276.01974
22833512
PubChem-compound
C7H15Cl2N2O2P
Cyclophosphamide
260.0248
H2O
Water
18.010565
C2H3ClO
Chloroacetaldehyde
77.98724
H2O2
Hydrogen peroxide
34.005478
C5H12ClN2O2P
3-Dechloroethylifosfamide
198.03249
HMDB0060689
HMDB
HMDB0060449
HMDB
NADH
BioCyc
Phosphoramide Aziridinium
HMDB0060686
HMDB
HMDB0060688
HMDB
NAD
BioCyc
NADP
HMDB0041822
HMDB
977
PubChem-compound
HMDB0059597
HMDB
Acrylic acid
7559
ChemSpider
Glutathione S-transferase Mu 1
7847
PubChem-compound
1.0
1.0
CHEBI:4027
ChEBI
1.0
SMILES
N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
NAD
86980
ChemSpider
CHEBI:238115
ChEBI
1.0