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17215925 ChemSpider 1.0 Cytochrome P450 2D6 Endoxifen 937 ChemSpider 1.0 Estrogen receptor 68037237 PubChem-compound 1.0 SMILES O alpha-Hydroxytamoxifen Norendoxifen 5460873 PubChem-compound 2616-64-0 CAS CHEBI:44616 ChEBI Cytochrome P450 3A4 Cytochrome P450 2B6 HMDB60667 HMDB Cytochrome P450 3A5 1.0 31750-48-8 CAS HMDB60666 HMDB Endoxifen ReactionCatalysis1698 ACTIVATION ReactionCatalysis1697 ACTIVATION HMDB61085 HMDB SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1 HMDB00935 HMDB C10H15N5O10P2 Adenosine 3',5'-diphosphate 427.02942 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1 ReactionCatalysis1695 ACTIVATION Endoxifen sulfate 53-59-8 CAS 1038 PubChem-compound Tamoxifen N-oxide CHEBI:17200 ChEBI 3036580 PubChem-compound CHEBI:16474 ChEBI 952 ChemSpider GO:0005829 GENE ONTOLOGY Dimethylaniline monooxygenase [N-oxide-forming] 3 Q01740 UniProt HMDB60585 HMDB HMDB59597 HMDB CH2O Formaldehyde 30.010565 2298470 ChemSpider 4-Hydroxytamoxifen 4-Hydroxytamoxifen-N-glucuronide 2300566 ChemSpider SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1 4'-Hydroxytamoxifen 1.0 Uridine 5'-diphosphate SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1 UDP-GLUCURONATE BioCyc 10540-29-1 CAS 6031 PubChem-compound Cytochrome P450 2B6 1.0 Sulfotransferase 1A1 1010 ChemSpider alpha-Hydroxytamoxifen 4-Hydroxytamoxifen sulfate ReactionCatalysis1477 ACTIVATION SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O CHEBI:63825 ChEBI C21H30N7O17P3 NADPH 745.0911 Hydrogen Ion 3-5-ADP BioCyc C21H29N7O17P3 NADP 744.08325 1.0 30778593 ChemSpider ReactionCatalysis1476 ACTIVATION CHEBI:41774 ChEBI SMILES CC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C1 C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 NADPH BioCyc SMILES CNCCOC1=CC=C(C=C1)C(=C(\[C@@H](C)O)C1=CC=CC=C1)\C1=CC=CC=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[O-])C=C1)C1=CC=CC=C1 1053-73-2 CAS FORMALDEHYDE BioCyc SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(O)C=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)CO[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 Reaction1736 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → Formaldehyde + N-Desmethyltamoxifen + NADP + Water LEFT_TO_RIGHT HMDB00217 HMDB 3033895 PubChem-compound HMDB01426 HMDB HMDB61328 HMDB Cytosol CHEBI:32663 ChEBI CPD-6641 BioCyc SMILES CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1 Dimethylaniline monooxygenase [N-oxide-forming] 1 UDP-glucuronosyltransferase 1-10 C05011 KEGG Compound Breast UDP-glucuronosyltransferase 1-4 SMILES C=O 692 ChemSpider Q9HAW8 UniProt SMILES CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 C26H29NO2 4-Hydroxytamoxifen 387.21982 SMILES CC\C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCNOC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 2733526 PubChem-compound C25H27NO2 Endoxifen 373.2042 HMDB00221 HMDB SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C1 C00007 KEGG Compound SMILES CCC(C(C1=CC=C(OCCNC)C=C1)C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1)C1=CC=CC=C1 C00006 KEGG Compound SMILES CC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1 CHEBI:18009 ChEBI 1.0 8266287 ChemSpider C00001 KEGG Compound 449459 PubChem-compound NADP 9799 ChemSpider C00005 KEGG Compound 1.0 NADPH 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 1.0 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 17473 PubChem-compound 159296 PubChem-compound 30778575 ChemSpider BiologicalState83 Oxygen SMP00471 SMPDB 1.0 53-57-6 CAS Phosphoadenosine phosphosulfate P31513 UniProt 4447687 ChemSpider 395987 ChemSpider 1.0 2.8.2.1 false 2.8.2.1 4-Hydroxytamoxifen + Phosphoadenosine phosphosulfate → 4-Hydroxytamoxifen sulfate + Adenosine 3',5'-diphosphate LEFT_TO_RIGHT C00015 KEGG Compound 4-Hydroxytamoxifen-O-glucuronide 2.4.1.17 false 2.4.1.17 Tamoxifen + Uridine diphosphate glucuronic acid → Tamoxifen-N-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Tamoxifen → 4'-Hydroxytamoxifen + NADP + Water LEFT_TO_RIGHT Reaction1870 false Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → NADP + Water + alpha-Hydroxy-N-desmethyl-tamoxifen LEFT_TO_RIGHT Reaction2165 false alpha-Hydroxytamoxifen → Alpha-Hydroxy-tamoxifen-O-glucuronide LEFT_TO_RIGHT NAD(P) BioCyc 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Tamoxifen → 4-Hydroxytamoxifen + NADP + Water LEFT_TO_RIGHT Formaldehyde Reaction2168 false NADP + Tamoxifen N-oxide + Water → Hydrogen Ion + NADPH + Oxygen + Tamoxifen LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 4-Hydroxytamoxifen + Uridine diphosphate glucuronic acid → 4-Hydroxytamoxifen-N-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT HMDB60808 HMDB H Hydrogen Ion 1.007825 CHEBI:16842 ChEBI 1.0 Reaction1869 false Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → Formaldehyde + N,N-Didesmethyltamoxifen + NADP + Water LEFT_TO_RIGHT 1.0 Cytochrome P450 2D6 GO:0005737 GENE ONTOLOGY HMDB13866 HMDB Reaction1866 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → NADP + Water + alpha-Hydroxytamoxifen LEFT_TO_RIGHT 4902110 ChemSpider 482-67-7 CAS Reaction1864 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → NADP + Tamoxifen N-oxide + Water LEFT_TO_RIGHT alpha-Hydroxy-N-desmethyl-tamoxifen CHEBI:17985 ChEBI Endoplasmic Reticulum CL:0000000 CELL TYPE ONTOLOGY C07108 KEGG Compound HMDB61125 HMDB UDP BioCyc CHEBI:17980 ChEBI ReactionCatalysis1722 ACTIVATION 1.0 ReactionCatalysis1723 ACTIVATION Reaction1776 false Endoxifen → Estrogen receptor LEFT_TO_RIGHT ReactionCatalysis2011 ACTIVATION ReactionCatalysis2012 ACTIVATION Reaction1772 false 4-Hydroxytamoxifen → Estrogen receptor LEFT_TO_RIGHT BTO:0000149 BRENDA TISSUE ONTOLOGY ReactionCatalysis2015 ACTIVATION 1.0 N,N-Didesmethyltamoxifen Estrogen receptor 5675 ChemSpider Sulfotransferase 1A1 1.0 C00167 KEGG Compound 1.14.14.1 false 1.14.14.1 Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → Endoxifen + NADP + Water LEFT_TO_RIGHT HMDB61124 HMDB 1.0 HMDB61123 HMDB 2.4.1.17 false 2.4.1.17 Endoxifen + Uridine diphosphate glucuronic acid → Endoxifen O-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Reaction2174 false Endoxifen → Norendoxifen LEFT_TO_RIGHT Water HMDB14813 HMDB 2.4.1.17 false 2.4.1.17 4-Hydroxytamoxifen + Uridine diphosphate glucuronic acid → 4-Hydroxytamoxifen-O-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Endoxifen O-glucuronide P50225 UniProt 2.8.2.1 false 2.8.2.1 Endoxifen + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Endoxifen sulfate LEFT_TO_RIGHT C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 ReactionCatalysis2020 ACTIVATION Cytoplasm Endoxifen ReactionCatalysis2022 ACTIVATION Cell Reaction1762 false 4-Hydroxytamoxifen + Hydrogen Ion + NADPH + Oxygen → Endoxifen + Formaldehyde + NADP + Water LEFT_TO_RIGHT 30778636 ChemSpider 10090750 PubChem-compound Endoxifen HMDB60616 HMDB C10H15N5O13P2S Phosphoadenosine phosphosulfate 506.98624 140102 ChemSpider Tamoxifen HMDB60615 HMDB C00054 KEGG Compound C00053 KEGG Compound 7732-18-5 CAS 75504-34-6 CAS O2 Oxygen 31.98983 1.0 ReactionCatalysis1504 ACTIVATION UDP-glucuronosyltransferase 1-10 ReactionCatalysis1503 ACTIVATION 1.0 GO:0005783 GENE ONTOLOGY 16522 ChemSpider UDP-glucuronosyltransferase 1-4 P03372 UniProt 1.0 30778623 ChemSpider C00067 KEGG Compound SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C1 Sulfotransferase 1A1 10214 PubChem-compound 3036172 PubChem-compound BiologicalState18 1.0 7782-44-7 CAS SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 6378383 PubChem-compound HMDB61140 HMDB P22310 UniProt 80234-20-4 CAS P20815 UniProt 30778630 ChemSpider Dimethylaniline monooxygenase [N-oxide-forming] 3 P20813 UniProt 9606 TAXONOMY 4-Hydroxytamoxifen 962 PubChem-compound P10635 UniProt 4574296 ChemSpider Alpha-Hydroxy-tamoxifen-O-glucuronide 1.0 1.0 1.0 58-98-0 CAS Uridine diphosphate glucuronic acid HMDB60513 HMDB SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 1.0 HMDB00295 HMDB HMDB02111 HMDB PAPS BioCyc 1.0 C00080 KEGG Compound SMILES O=O 1.0 5284643 PubChem-compound Dimethylaniline monooxygenase [N-oxide-forming] 1 1.0 Adenosine 3',5'-diphosphate 2.0 5809 ChemSpider CHEBI:15377 ChEBI 1.0 CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] P08684 UniProt 1.0 712 PubChem-compound 5886 PubChem-compound HMDB00061 HMDB C24H25NO N,N-Didesmethyltamoxifen 343.1936 PW000250 PathWhiz HMDB60622 HMDB ReactionCatalysis1499 ACTIVATION C16546 KEGG Compound C16547 KEGG Compound C16548 KEGG Compound C16544 KEGG Compound C16545 KEGG Compound ReactionCatalysis1497 ACTIVATION C26H29NO2 Tamoxifen N-oxide 387.21982 Tamoxifen-N-glucuronide C25H27NO2 alpha-Hydroxy-N-desmethyl-tamoxifen 373.2042 C26H29NO2 alpha-Hydroxytamoxifen 387.21982 Estrogen receptor C32H37NO8 Alpha-Hydroxy-tamoxifen-O-glucuronide 563.2519 C26H29NO2 4'-Hydroxytamoxifen 387.21982 C32H38NO7 Tamoxifen-N-glucuronide 548.26483 C26H29NO5S 4-Hydroxytamoxifen sulfate 467.17664 97151-02-5 CAS 1.0 Cytochrome P450 3A5 68392-35-8 CAS SMILES O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O 112093-28-4 CAS 22833512 PubChem-compound Cytochrome P450 3A4 H2O Water 18.010565 N-Desmethyltamoxifen 2300247 ChemSpider C30H33NO9 4-Hydroxytamoxifen-N-glucuronide 551.2155 HMDB01377 HMDB C32H37NO8 4-Hydroxytamoxifen-O-glucuronide 563.2519 HMDB01134 HMDB C25H27NO5S Endoxifen sulfate 453.16098 Transport222 false 4-Hydroxytamoxifen (→) Transport: Homo sapiens, Liver, Cell, Cytoplasm to Homo sapiens, Breast, Cell, Cytoplasm LEFT_TO_RIGHT C31H37NO8 Endoxifen O-glucuronide 551.2519 Tamoxifen Action Pathway C24H25NO2 Norendoxifen 359.18854 Transport221 false Endoxifen (→) Transport: Homo sapiens, Liver, Cell, Cytoplasm to Homo sapiens, Breast, Cell, Cytoplasm LEFT_TO_RIGHT CHEBI:17659 ChEBI 977 PubChem-compound 50-00-0 CAS 2015313 ChemSpider 1.0 ReactionCatalysis2006 ACTIVATION HMDB60530 HMDB ReactionCatalysis2008 ACTIVATION C25H27NO N-Desmethyltamoxifen 357.20926 ReactionCatalysis2007 ACTIVATION ReactionCatalysis2009 ACTIVATION 1.0 C26H29NO Tamoxifen 371.2249 Estrogen receptor Cytochrome P450 3A4 Cytochrome P450 2D6 Cytochrome P450 2B6 UDP- glucuronosyltransferase 1-4 Dimethylaniline monooxygenase [N-oxide- forming] 3 Dimethylaniline monooxygenase [N-oxide- forming] 1 Cytochrome P450 3A4 Cytochrome P450 2D6 UDP- glucuronosyltransferase 1-4 UDP- glucuronosyltransferase 1-4 Sulfotransferase 1A1 Cytochrome P450 3A4 Cytochrome P450 3A5 Cytochrome P450 3A4 Cytochrome P450 3A5 Cytochrome P450 2D6 UDP- glucuronosyltransferase 1-10 Cytochrome P450 3A4 Cytochrome P450 3A4 Sulfotransferase 1A1 Endoxifen 4-Hydroxytamoxifen alpha-Hydroxytamoxifen Alpha-Hydroxy-tamoxifen-O- glucuronide Endoxifen Norendoxifen Tamoxifen NADPH H + O 2 H 2 O NADP NADPH H + O 2 4'-Hydroxytamoxifen H 2 O NADP Uridine diphosphate glucuronic acid Tamoxifen-N-glucuronide Uridine 5'-diphosphate NADPH H + O 2 Tamoxifen N-oxide NADP H 2 O H 2 O NADP O 2 NADPH H + NADPH H + O 2 4-Hydroxytamoxifen NADP H 2 O Uridine diphosphate glucuronic acid 4-Hydroxytamoxifen-O- glucuronide Uridine 5'-diphosphate Uridine diphosphate glucuronic acid 4-Hydroxytamoxifen-N- glucuronide Uridine 5'-diphosphate Phosphoadenosine phosphosulfate 4-Hydroxytamoxifen sulfate Adenosine 3',5'- diphosphate O 2 NADPH H + N-Desmethyltamoxifen H 2 O Formaldehyde NADP O 2 NADPH H + H 2 O Formaldehyde NADP NADPH H + O 2 H 2 O NADP Uridine diphosphate glucuronic acid Endoxifen O-glucuronide Uridine 5'-diphosphate O 2 NADPH H + alpha-Hydroxy-N-desmethyl- tamoxifen H 2 O NADP O 2 NADPH H + N,N-Didesmethyltamoxifen H 2 O NADP Formaldehyde Phosphoadenosine phosphosulfate Endoxifen sulfate Adenosine 3',5'- diphosphate Heme Heme Heme FAD FAD Heme Heme Heme Heme Heme Heme Heme Heme Heme Hepatocyte Breast Cancer Cell Endoplasmic Reticulum Membrane
17215925 ChemSpider 1.0 Cytochrome P450 2D6 Endoxifen 937 ChemSpider 1.0 Estrogen receptor 68037237 PubChem-compound 1.0 SMILES O alpha-Hydroxytamoxifen Norendoxifen 5460873 PubChem-compound 2616-64-0 CAS CHEBI:44616 ChEBI Cytochrome P450 3A4 Cytochrome P450 2B6 HMDB60667 HMDB Cytochrome P450 3A5 1.0 31750-48-8 CAS HMDB60666 HMDB Endoxifen ReactionCatalysis1698 ACTIVATION ReactionCatalysis1697 ACTIVATION HMDB61085 HMDB SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1 HMDB00935 HMDB C10H15N5O10P2 Adenosine 3',5'-diphosphate 427.02942 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1 ReactionCatalysis1695 ACTIVATION Endoxifen sulfate 53-59-8 CAS 1038 PubChem-compound Tamoxifen N-oxide CHEBI:17200 ChEBI 3036580 PubChem-compound CHEBI:16474 ChEBI 952 ChemSpider GO:0005829 GENE ONTOLOGY Dimethylaniline monooxygenase [N-oxide-forming] 3 Q01740 UniProt HMDB60585 HMDB HMDB59597 HMDB CH2O Formaldehyde 30.010565 2298470 ChemSpider 4-Hydroxytamoxifen 4-Hydroxytamoxifen-N-glucuronide 2300566 ChemSpider SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCNC)C=C1)C1=CC=CC=C1 4'-Hydroxytamoxifen 1.0 Uridine 5'-diphosphate SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1 UDP-GLUCURONATE BioCyc 10540-29-1 CAS 6031 PubChem-compound Cytochrome P450 2B6 1.0 Sulfotransferase 1A1 1010 ChemSpider alpha-Hydroxytamoxifen 4-Hydroxytamoxifen sulfate ReactionCatalysis1477 ACTIVATION SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O CHEBI:63825 ChEBI C21H30N7O17P3 NADPH 745.0911 Hydrogen Ion 3-5-ADP BioCyc C21H29N7O17P3 NADP 744.08325 1.0 30778593 ChemSpider ReactionCatalysis1476 ACTIVATION CHEBI:41774 ChEBI SMILES CC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C1 C15H22N2O18P2 Uridine diphosphate glucuronic acid 580.0343 NADPH BioCyc SMILES CNCCOC1=CC=C(C=C1)C(=C(\[C@@H](C)O)C1=CC=CC=C1)\C1=CC=CC=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[O-])C=C1)C1=CC=CC=C1 1053-73-2 CAS FORMALDEHYDE BioCyc SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(O)C=C1 SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)CO[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 Reaction1736 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → Formaldehyde + N-Desmethyltamoxifen + NADP + Water LEFT_TO_RIGHT HMDB00217 HMDB 3033895 PubChem-compound HMDB01426 HMDB HMDB61328 HMDB Cytosol CHEBI:32663 ChEBI CPD-6641 BioCyc SMILES CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1 Dimethylaniline monooxygenase [N-oxide-forming] 1 UDP-glucuronosyltransferase 1-10 C05011 KEGG Compound Breast UDP-glucuronosyltransferase 1-4 SMILES C=O 692 ChemSpider Q9HAW8 UniProt SMILES CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 C26H29NO2 4-Hydroxytamoxifen 387.21982 SMILES CC\C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCNOC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1 2733526 PubChem-compound C25H27NO2 Endoxifen 373.2042 HMDB00221 HMDB SMILES CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C1 C00007 KEGG Compound SMILES CCC(C(C1=CC=C(OCCNC)C=C1)C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1)C1=CC=CC=C1 C00006 KEGG Compound SMILES CC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1 CHEBI:18009 ChEBI 1.0 8266287 ChemSpider C00001 KEGG Compound 449459 PubChem-compound NADP 9799 ChemSpider C00005 KEGG Compound 1.0 NADPH 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 1.0 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 17473 PubChem-compound 159296 PubChem-compound 30778575 ChemSpider BiologicalState83 Homo sapiens, Breast, Cell, Cytoplasm Oxygen http://identifiers.org/smpdb/SMP00471 SMPDB 1.0 53-57-6 CAS Phosphoadenosine phosphosulfate P31513 UniProt 4447687 ChemSpider 395987 ChemSpider 1.0 2.8.2.1 false 2.8.2.1 4-Hydroxytamoxifen + Phosphoadenosine phosphosulfate → 4-Hydroxytamoxifen sulfate + Adenosine 3',5'-diphosphate LEFT_TO_RIGHT C00015 KEGG Compound 4-Hydroxytamoxifen-O-glucuronide 2.4.1.17 false 2.4.1.17 Tamoxifen + Uridine diphosphate glucuronic acid → Tamoxifen-N-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Tamoxifen → 4'-Hydroxytamoxifen + NADP + Water LEFT_TO_RIGHT Reaction1870 false Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → NADP + Water + alpha-Hydroxy-N-desmethyl-tamoxifen LEFT_TO_RIGHT Reaction2165 false alpha-Hydroxytamoxifen → Alpha-Hydroxy-tamoxifen-O-glucuronide LEFT_TO_RIGHT NAD(P) BioCyc 1.14.14.1 false 1.14.14.1 Hydrogen Ion + NADPH + Oxygen + Tamoxifen → 4-Hydroxytamoxifen + NADP + Water LEFT_TO_RIGHT Formaldehyde Reaction2168 false NADP + Tamoxifen N-oxide + Water → Hydrogen Ion + NADPH + Oxygen + Tamoxifen LEFT_TO_RIGHT 2.4.1.17 false 2.4.1.17 4-Hydroxytamoxifen + Uridine diphosphate glucuronic acid → 4-Hydroxytamoxifen-N-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT HMDB60808 HMDB H Hydrogen Ion 1.007825 CHEBI:16842 ChEBI 1.0 Reaction1869 false Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → Formaldehyde + N,N-Didesmethyltamoxifen + NADP + Water LEFT_TO_RIGHT 1.0 Cytochrome P450 2D6 GO:0005737 GENE ONTOLOGY HMDB13866 HMDB Reaction1866 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → NADP + Water + alpha-Hydroxytamoxifen LEFT_TO_RIGHT 4902110 ChemSpider 482-67-7 CAS Reaction1864 false Hydrogen Ion + NADPH + Oxygen + Tamoxifen → NADP + Tamoxifen N-oxide + Water LEFT_TO_RIGHT alpha-Hydroxy-N-desmethyl-tamoxifen CHEBI:17985 ChEBI Endoplasmic Reticulum CL:0000000 CELL TYPE ONTOLOGY C07108 KEGG Compound HMDB61125 HMDB UDP BioCyc CHEBI:17980 ChEBI ReactionCatalysis1722 ACTIVATION 1.0 ReactionCatalysis1723 ACTIVATION Reaction1776 false Endoxifen → Estrogen receptor LEFT_TO_RIGHT ReactionCatalysis2011 ACTIVATION ReactionCatalysis2012 ACTIVATION Reaction1772 false 4-Hydroxytamoxifen → Estrogen receptor LEFT_TO_RIGHT BTO:0000149 BRENDA TISSUE ONTOLOGY ReactionCatalysis2015 ACTIVATION 1.0 N,N-Didesmethyltamoxifen Estrogen receptor 5675 ChemSpider Sulfotransferase 1A1 1.0 C00167 KEGG Compound 1.14.14.1 false 1.14.14.1 Hydrogen Ion + N-Desmethyltamoxifen + NADPH + Oxygen → Endoxifen + NADP + Water LEFT_TO_RIGHT HMDB61124 HMDB 1.0 HMDB61123 HMDB 2.4.1.17 false 2.4.1.17 Endoxifen + Uridine diphosphate glucuronic acid → Endoxifen O-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Reaction2174 false Endoxifen → Norendoxifen LEFT_TO_RIGHT Water HMDB14813 HMDB 2.4.1.17 false 2.4.1.17 4-Hydroxytamoxifen + Uridine diphosphate glucuronic acid → 4-Hydroxytamoxifen-O-glucuronide + Uridine 5'-diphosphate LEFT_TO_RIGHT Endoxifen O-glucuronide P50225 UniProt 2.8.2.1 false 2.8.2.1 Endoxifen + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Endoxifen sulfate LEFT_TO_RIGHT C9H14N2O12P2 Uridine 5'-diphosphate 404.0022 ReactionCatalysis2020 ACTIVATION Cytoplasm Endoxifen ReactionCatalysis2022 ACTIVATION Cell Reaction1762 false 4-Hydroxytamoxifen + Hydrogen Ion + NADPH + Oxygen → Endoxifen + Formaldehyde + NADP + Water LEFT_TO_RIGHT 30778636 ChemSpider 10090750 PubChem-compound Endoxifen HMDB60616 HMDB C10H15N5O13P2S Phosphoadenosine phosphosulfate 506.98624 140102 ChemSpider Tamoxifen HMDB60615 HMDB C00054 KEGG Compound C00053 KEGG Compound 7732-18-5 CAS 75504-34-6 CAS O2 Oxygen 31.98983 1.0 ReactionCatalysis1504 ACTIVATION UDP-glucuronosyltransferase 1-10 ReactionCatalysis1503 ACTIVATION 1.0 GO:0005783 GENE ONTOLOGY 16522 ChemSpider UDP-glucuronosyltransferase 1-4 P03372 UniProt 1.0 30778623 ChemSpider C00067 KEGG Compound SMILES CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C1 Sulfotransferase 1A1 10214 PubChem-compound 3036172 PubChem-compound BiologicalState18 Homo sapiens, Cell, Endoplasmic Reticulum 1.0 7782-44-7 CAS SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 6378383 PubChem-compound HMDB61140 HMDB P22310 UniProt 80234-20-4 CAS P20815 UniProt 30778630 ChemSpider Dimethylaniline monooxygenase [N-oxide-forming] 3 P20813 UniProt 9606 TAXONOMY 4-Hydroxytamoxifen 962 PubChem-compound P10635 UniProt 4574296 ChemSpider Alpha-Hydroxy-tamoxifen-O-glucuronide 1.0 1.0 1.0 58-98-0 CAS Uridine diphosphate glucuronic acid HMDB60513 HMDB SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O 1.0 HMDB00295 HMDB HMDB02111 HMDB PAPS BioCyc 1.0 C00080 KEGG Compound SMILES O=O 1.0 5284643 PubChem-compound Dimethylaniline monooxygenase [N-oxide-forming] 1 1.0 Adenosine 3',5'-diphosphate 2.0 5809 ChemSpider CHEBI:15377 ChEBI 1.0 CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] P08684 UniProt 1.0 712 PubChem-compound 5886 PubChem-compound HMDB00061 HMDB C24H25NO N,N-Didesmethyltamoxifen 343.1936 PW000250 PathWhiz HMDB60622 HMDB ReactionCatalysis1499 ACTIVATION C16546 KEGG Compound C16547 KEGG Compound C16548 KEGG Compound C16544 KEGG Compound C16545 KEGG Compound ReactionCatalysis1497 ACTIVATION C26H29NO2 Tamoxifen N-oxide 387.21982 Tamoxifen-N-glucuronide C25H27NO2 alpha-Hydroxy-N-desmethyl-tamoxifen 373.2042 C26H29NO2 alpha-Hydroxytamoxifen 387.21982 Estrogen receptor C32H37NO8 Alpha-Hydroxy-tamoxifen-O-glucuronide 563.2519 C26H29NO2 4'-Hydroxytamoxifen 387.21982 C32H38NO7 Tamoxifen-N-glucuronide 548.26483 C26H29NO5S 4-Hydroxytamoxifen sulfate 467.17664 97151-02-5 CAS 1.0 Cytochrome P450 3A5 68392-35-8 CAS SMILES O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O 112093-28-4