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17215925 ChemSpider 6022 PubChem-compound Doxorubicin-semiquinone 937 ChemSpider 8652398 ChemSpider 1.0 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial Doxorubicin 439153 PubChem-compound SMILES O HMDB0060822 HMDB 1.0 Doxorubicin HMDB0041884 HMDB Doxorubicin-semiquinone 1.0 Q92887 UniProt NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial HMDB0000538 HMDB 1.0 C27H31NO11 Doxorubicin-semiquinone 545.1897 ATP BioCyc C21H20O8 Doxorubicinol deoxaglycone 400.1158 C21H18O9 Doxorubicine hydroxyaglycone 414.0951 1.0 C21H20O9 Doxorubicinol hydroxyaglycone 416.11072 1.0 CHEBI:15846 ChEBI SMP0000650 SMPDB ADP BioCyc NADH P29474 UniProt Q15311 UniProt CL:0000182 CELL TYPE ONTOLOGY 53-59-8 CAS BTO:0000759 BRENDA TISSUE ONTOLOGY NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial 1.0 C01661 KEGG Compound 2.0 5742 ChemSpider CHEBI:16474 ChEBI Solute carrier family 22 member 16 ReactionCatalysis1902 ACTIVATION 65332 ChemSpider ReactionCatalysis1901 ACTIVATION 1.0 Q86VW1 UniProt P16152 UniProt CHEBI:16908 ChEBI Carbonyl reductase [NADPH] 1 1.0 HMDB0061231 HMDB Phosphate HMDB0061232 HMDB ReactionCatalysis1904 ACTIVATION O4P Phosphate 94.95342 ReactionCatalysis1903 ACTIVATION HMDB0015132 HMDB 1.0 ReactionCatalysis1906 ACTIVATION ReactionCatalysis1908 ACTIVATION ReactionCatalysis1907 ACTIVATION ReactionCatalysis1909 ACTIVATION NADPH--cytochrome P450 reductase NAD Xanthine dehydrogenase/oxidase ReactionCatalysis1913 ACTIVATION ATP-binding cassette sub-family G member 2 ReactionCatalysis1912 ACTIVATION NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 Mitochondrion ReactionCoupledTransportCatalysis87 ACTIVATION ReactionCoupledTransportCatalysis86 ACTIVATION ReactionCoupledTransportCatalysis89 ACTIVATION ReactionCoupledTransportCatalysis88 ACTIVATION NADPH BioCyc Doxorubicin-semiquinone Multidrug resistance-associated protein 1 O75306 UniProt TransportCatalysis161 ACTIVATION TransportCatalysis160 ACTIVATION NADPH--cytochrome P450 reductase 58-68-4 CAS 31703 PubChem-compound 2.0 SMILES [O-]P([O-])([O-])=O 1.0 HMDB0000217 HMDB 45038813 PubChem-compound GO:0005886 GENE ONTOLOGY 1.0 1.0 TransportCatalysis159 ACTIVATION TransportCatalysis158 ACTIVATION Doxorubicinol TransportCatalysis157 ACTIVATION TransportCatalysis156 ACTIVATION 1.0 C00009 KEGG Compound NADH C00008 KEGG Compound C00006 KEGG Compound C27H31NO11 Doxorubicinol 545.1897 CHEBI:18009 ChEBI C00001 KEGG Compound HMDB0001429 HMDB 1.0 C00005 KEGG Compound C00004 KEGG Compound CHEBI:18367 ChEBI NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial C00003 KEGG Compound 1032 ChemSpider NADP Liver C00002 KEGG Compound 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 Aldo-keto reductase family 1 member C3 HMDB0000221 HMDB 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 Mitochondrial Inner Membrane 53-57-6 CAS 1.0 C21H28N7O14P2 NAD 664.11694 ATP-binding cassette sub-family G member 2 HMDB0000902 HMDB Extracellular Space Alcohol dehydrogenase [NADP(+)] P47989 UniProt NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 Aldo-keto reductase family 1 member C3 5957 PubChem-compound BiologicalState53 Homo sapiens, Liver, Hepatocyte GO:0005743 GENE ONTOLOGY Hepatocyte 10476988 PubChem-compound Doxorubicin Solute carrier family 22 member 16 56-65-5 CAS 53-84-9 CAS P08183 UniProt 1.14.13.39 false 1.14.13.39 Doxorubicin + NADH → Doxorubicin-semiquinone + NAD LEFT_TO_RIGHT Reaction2035 false Doxorubicin → Doxorubicinol deoxaglycone LEFT_TO_RIGHT Reaction2032 false Doxorubicin + NADPH → Doxorubicinol + NADP LEFT_TO_RIGHT GO:0005739 GENE ONTOLOGY 1.0 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial GO:0005615 GENE ONTOLOGY C10H15N5O10P2 Adenosine diphosphate 427.02942 GO:0005737 GENE ONTOLOGY PW000626 PathWhiz C27H29NO11 Doxorubicin 543.1741 Reaction2036 false Doxorubicin → Doxorubicine hydroxyaglycone LEFT_TO_RIGHT Reaction2037 false Doxorubicine hydroxyaglycone → Doxorubicinol hydroxyaglycone LEFT_TO_RIGHT Transport198 false Doxorubicin (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Transport199 false Doxorubicin (→) Transport: Homo sapiens, Cell, Cytoplasm to Homo sapiens, Extracellular Space LEFT_TO_RIGHT 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 CPD-8587 BioCyc Multidrug resistance-associated protein 1 1.0 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 Nitric-oxide synthase, endothelial Adenosine triphosphate 75768 ChemSpider HMDB0001341 HMDB Carbonyl reductase [NADPH] 3 23214-92-8 CAS Carbonyl reductase [NADPH] 1 Canalicular multispecific organic anion transporter 1 5675 ChemSpider RalA-binding protein 1 Water NAD(P)H dehydrogenase [quinone] 1 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ReactionCoupledTransport74 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT ReactionCoupledTransport73 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT 1.0 Multidrug resistance protein 1 2.0 NAD 54193-28-1 CAS Cytoplasm 1.0 SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O NADPH ReactionCoupledTransport72 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT 3.6.3.44 false 3.6.3.44 Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT CHEBI:15422 ChEBI Nitric oxide synthase, endothelial 1.0 Homo sapiens Multidrug resistance protein 1 388299 ChemSpider 7732-18-5 CAS NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial O75489 UniProt HMDB0001487 HMDB P16435 UniProt GO:0005789 GENE ONTOLOGY CHEBI:28748 ChEBI Doxorubicin Xanthine dehydrogenase/oxidase ATP-binding cassette sub-family G member 2 C10H16N5O13P3 Adenosine triphosphate 506.99576 83970 PubChem-compound BiologicalState10 Homo sapiens, Liver CHEBI:16761 ChEBI Doxorubicin-semiquinone Reaction2073 false Doxorubicin-semiquinone → Doxorubicin LEFT_TO_RIGHT Doxorubicinol hydroxyaglycone 9606 TAXONOMY 962 PubChem-compound 1.0 Canalicular multispecific organic anion transporter 1 O75828 UniProt 5800 ChemSpider ReactionCatalysis1915 ACTIVATION ReactionCatalysis1914 ACTIVATION ReactionCatalysis1916 ACTIVATION 5893 PubChem-compound 1.0 P14550 UniProt 72401 PubChem-compound HMDB0002111 HMDB Cell Membrane CHEBI:15377 ChEBI Doxorubicinol deoxaglycone Multidrug resistance-associated protein 1 NAD(P)H dehydrogenase [quinone] 1 14265-44-2 CAS 58-64-0 CAS SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O 5886 PubChem-compound Nitric oxide synthase, endothelial O75251 UniProt Alcohol dehydrogenase [NADP(+)] HMDB0061206 HMDB Transport202 false Doxorubicin-semiquinone (↔) Transport: Homo sapiens, Cell, Mitochondrion to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Transport201 false Doxorubicin (↔) Transport: Homo sapiens, Cell, Cytoplasm to Homo sapiens, Cell, Mitochondrion LEFT_TO_RIGHT NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial 29400 ChemSpider 23935799 ChemSpider RalA-binding protein 1 1.0 Canalicular multispecific organic anion transporter 1 Doxorubicin Metabolism Pathway 22833512 PubChem-compound P42330 UniProt H2O Water 18.010565 Carbonyl reductase [NADPH] 3 NADH BioCyc Xanthine dehydrogenase/oxidase Doxorubicine hydroxyaglycone NAD BioCyc 1061 PubChem-compound Q9UNQ0 UniProt NAD(P)H dehydrogenase [quinone] 1 Multidrug resistance protein 1 SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(CC3)C(O)CO)C(O)=C1C2=O SMILES COC1=CC=CC2=C1C([O-])C1=C(C2[O-])C(O)=C2CC(O)(CC(OC3CC(N)C(O)C(C)O3)C2=C1O)C(=O)CO SMILES COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C3=C1O)[C@@H](O)CO)C2=O P15559 UniProt P33527 UniProt SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(O)CO)C(O)=C1C2=O SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(=O)CO)C(O)=C1C2=O Adenosine diphosphate 1.0 Doxorubicin Doxorubicin NAD Solute carrier family 22 member 16 Multidrug resistance protein 1 Multidrug resistance- associated protein 1 Canalicular multispecific organic anion transporter 1 ATP-binding cassette sub-family G member 2 RalA-binding protein 1 NAD(P)H dehydrogenase [quinone] 1 NADPH-- cytochrome P450 reductase Xanthine dehydrogenase/oxidase Carbonyl reductase [NADPH] 1 Carbonyl reductase [NADPH] 3 Aldo-keto reductase family 1 member C3 Alcohol dehydrogenase [NADP(+)] Nitric oxide synthase, endothelial Xanthine dehydrogenase/oxidase NAD(P)H dehydrogenase [quinone] 1 NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial Doxorubicin Doxorubicin Doxorubicin Doxorubicin-semiquinone Doxorubicin Doxorubicine hydroxyaglycone Doxorubicinol hydroxyaglycone Doxorubicinol deoxaglycone Doxorubicin-semiquinone NADPH Doxorubicinol NADP NADH NAD NADH NAD NADH NAD H 2 O ATP P i ADP H 2 O ATP P i ADP H 2 O ATP P i ADP H 2 O ATP P i ADP FAD FAD Flavin Mononucleotide FAD 2Fe-2S Molybdopterin Heme FAD Flavin Mononucleotide Tetrahydrobiopterin FAD 2Fe-2S Molybdopterin FAD Sarcoplasmic reticulum Mitochondrion
17215925 ChemSpider 6022 PubChem-compound Doxorubicin-semiquinone 937 ChemSpider 8652398 ChemSpider 1.0 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial Doxorubicin 439153 PubChem-compound SMILES O HMDB0060822 HMDB 1.0 Doxorubicin HMDB0041884 HMDB Doxorubicin-semiquinone 1.0 Q92887 UniProt NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial HMDB0000538 HMDB 1.0 C27H31NO11 Doxorubicin-semiquinone 545.1897 ATP BioCyc C21H20O8 Doxorubicinol deoxaglycone 400.1158 C21H18O9 Doxorubicine hydroxyaglycone 414.0951 1.0 C21H20O9 Doxorubicinol hydroxyaglycone 416.11072 1.0 CHEBI:15846 ChEBI SMP0000650 SMPDB ADP BioCyc NADH P29474 UniProt Q15311 UniProt CL:0000182 CELL TYPE ONTOLOGY 53-59-8 CAS BTO:0000759 BRENDA TISSUE ONTOLOGY NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial 1.0 C01661 KEGG Compound 2.0 5742 ChemSpider CHEBI:16474 ChEBI Solute carrier family 22 member 16 ReactionCatalysis1902 ACTIVATION 65332 ChemSpider ReactionCatalysis1901 ACTIVATION 1.0 Q86VW1 UniProt P16152 UniProt CHEBI:16908 ChEBI Carbonyl reductase [NADPH] 1 1.0 HMDB0061231 HMDB Phosphate HMDB0061232 HMDB ReactionCatalysis1904 ACTIVATION O4P Phosphate 94.95342 ReactionCatalysis1903 ACTIVATION HMDB0015132 HMDB 1.0 ReactionCatalysis1906 ACTIVATION ReactionCatalysis1908 ACTIVATION ReactionCatalysis1907 ACTIVATION ReactionCatalysis1909 ACTIVATION NADPH--cytochrome P450 reductase NAD Xanthine dehydrogenase/oxidase ReactionCatalysis1913 ACTIVATION ATP-binding cassette sub-family G member 2 ReactionCatalysis1912 ACTIVATION NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial C21H30N7O17P3 NADPH 745.0911 C21H29N7O17P3 NADP 744.08325 Mitochondrion ReactionCoupledTransportCatalysis87 ACTIVATION ReactionCoupledTransportCatalysis86 ACTIVATION ReactionCoupledTransportCatalysis89 ACTIVATION ReactionCoupledTransportCatalysis88 ACTIVATION NADPH BioCyc Doxorubicin-semiquinone Multidrug resistance-associated protein 1 O75306 UniProt TransportCatalysis161 ACTIVATION TransportCatalysis160 ACTIVATION NADPH--cytochrome P450 reductase 58-68-4 CAS 31703 PubChem-compound 2.0 SMILES [O-]P([O-])([O-])=O 1.0 HMDB0000217 HMDB 45038813 PubChem-compound GO:0005886 GENE ONTOLOGY 1.0 1.0 TransportCatalysis159 ACTIVATION TransportCatalysis158 ACTIVATION Doxorubicinol TransportCatalysis157 ACTIVATION TransportCatalysis156 ACTIVATION 1.0 C00009 KEGG Compound NADH C00008 KEGG Compound C00006 KEGG Compound C27H31NO11 Doxorubicinol 545.1897 CHEBI:18009 ChEBI C00001 KEGG Compound HMDB0001429 HMDB 1.0 C00005 KEGG Compound C00004 KEGG Compound CHEBI:18367 ChEBI NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial C00003 KEGG Compound 1032 ChemSpider NADP Liver C00002 KEGG Compound 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 Aldo-keto reductase family 1 member C3 HMDB0000221 HMDB 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 Mitochondrial Inner Membrane 53-57-6 CAS 1.0 C21H28N7O14P2 NAD 664.11694 ATP-binding cassette sub-family G member 2 HMDB0000902 HMDB Extracellular Space Alcohol dehydrogenase [NADP(+)] P47989 UniProt NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NAD(P) BioCyc C21H29N7O14P2 NADH 665.12476 Aldo-keto reductase family 1 member C3 5957 PubChem-compound BiologicalState53 Homo sapiens, Liver, Hepatocyte GO:0005743 GENE ONTOLOGY Hepatocyte 10476988 PubChem-compound Doxorubicin Solute carrier family 22 member 16 56-65-5 CAS 53-84-9 CAS P08183 UniProt 1.14.13.39 false 1.14.13.39 Doxorubicin + NADH → Doxorubicin-semiquinone + NAD LEFT_TO_RIGHT Reaction2035 false Doxorubicin → Doxorubicinol deoxaglycone LEFT_TO_RIGHT Reaction2032 false Doxorubicin + NADPH → Doxorubicinol + NADP LEFT_TO_RIGHT GO:0005739 GENE ONTOLOGY 1.0 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial GO:0005615 GENE ONTOLOGY C10H15N5O10P2 Adenosine diphosphate 427.02942 GO:0005737 GENE ONTOLOGY PW000626 PathWhiz C27H29NO11 Doxorubicin 543.1741 Reaction2036 false Doxorubicin → Doxorubicine hydroxyaglycone LEFT_TO_RIGHT Reaction2037 false Doxorubicine hydroxyaglycone → Doxorubicinol hydroxyaglycone LEFT_TO_RIGHT Transport198 false Doxorubicin (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Transport199 false Doxorubicin (→) Transport: Homo sapiens, Cell, Cytoplasm to Homo sapiens, Extracellular Space LEFT_TO_RIGHT 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 CPD-8587 BioCyc Multidrug resistance-associated protein 1 1.0 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 Nitric-oxide synthase, endothelial Adenosine triphosphate 75768 ChemSpider HMDB0001341 HMDB Carbonyl reductase [NADPH] 3 23214-92-8 CAS Carbonyl reductase [NADPH] 1 Canalicular multispecific organic anion transporter 1 5675 ChemSpider RalA-binding protein 1 Water NAD(P)H dehydrogenase [quinone] 1 SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ReactionCoupledTransport74 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT ReactionCoupledTransport73 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT 1.0 Multidrug resistance protein 1 2.0 NAD 54193-28-1 CAS Cytoplasm 1.0 SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O NADPH ReactionCoupledTransport72 false Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT 3.6.3.44 false 3.6.3.44 Adenosine triphosphate + Doxorubicin + Water → Adenosine diphosphate + Doxorubicin + Phosphate LEFT_TO_RIGHT CHEBI:15422 ChEBI Nitric oxide synthase, endothelial 1.0 Homo sapiens Multidrug resistance protein 1 388299 ChemSpider 7732-18-5 CAS NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial O75489 UniProt HMDB0001487 HMDB P16435 UniProt GO:0005789 GENE ONTOLOGY CHEBI:28748 ChEBI Doxorubicin Xanthine dehydrogenase/oxidase ATP-binding cassette sub-family G member 2 C10H16N5O13P3 Adenosine triphosphate 506.99576 83970 PubChem-compound BiologicalState10 Homo sapiens, Liver CHEBI:16761 ChEBI Doxorubicin-semiquinone Reaction2073 false Doxorubicin-semiquinone → Doxorubicin LEFT_TO_RIGHT Doxorubicinol hydroxyaglycone 9606 TAXONOMY 962 PubChem-compound 1.0 Canalicular multispecific organic anion transporter 1 O75828 UniProt 5800 ChemSpider ReactionCatalysis1915 ACTIVATION ReactionCatalysis1914 ACTIVATION ReactionCatalysis1916 ACTIVATION 5893 PubChem-compound 1.0 P14550 UniProt 72401 PubChem-compound HMDB0002111 HMDB Cell Membrane CHEBI:15377 ChEBI Doxorubicinol deoxaglycone Multidrug resistance-associated protein 1 NAD(P)H dehydrogenase [quinone] 1 14265-44-2 CAS 58-64-0 CAS SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O 5886 PubChem-compound Nitric oxide synthase, endothelial O75251 UniProt Alcohol dehydrogenase [NADP(+)] HMDB0061206 HMDB Transport202 false Doxorubicin-semiquinone (↔) Transport: Homo sapiens, Cell, Mitochondrion to Homo sapiens, Cell, Cytoplasm LEFT_TO_RIGHT Transport201 false Doxorubicin (↔) Transport: Homo sapiens, Cell, Cytoplasm to Homo sapiens, Cell, Mitochondrion LEFT_TO_RIGHT NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial 29400 ChemSpider 23935799 ChemSpider RalA-binding protein 1 1.0 Canalicular multispecific organic anion transporter 1 Doxorubicin Metabolism Pathway 22833512 PubChem-compound P42330 UniProt H2O Water 18.010565 Carbonyl reductase [NADPH] 3 NADH BioCyc Xanthine dehydrogenase/oxidase Doxorubicine hydroxyaglycone NAD BioCyc 1061 PubChem-compound Q9UNQ0 UniProt NAD(P)H dehydrogenase [quinone] 1 Multidrug resistance protein 1 SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(CC3)C(O)CO)C(O)=C1C2=O SMILES COC1=CC=CC2=C1C([O-])C1=C(C2[O-])C(O)=C2CC(O)(CC(OC3CC(N)C(O)C(C)O3)C2=C1O)C(=O)CO SMILES COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C3=C1O)[C@@H](O)CO)C2=O P15559 UniProt P33527 UniProt SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(O)CO)C(O)=C1C2=O SMILES COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O)C(=O)CO)C(O)=C1C2=O Adenosine diphosphate 1.0 Doxorubicin Doxorubicin NAD Mitochondria SLC22A16 ABCB1 ABCC1 ABCC2 ABCG2 RALBP1 NQO1 POR XDH CBR1 CBR3 AKR1C3 AKR1A1 NOS3 XDH NQO1 NDUFS2 NDUFS3 NDUFS7 NDUFS2 NDUFS3 NDUFS7 Doxorubicin Doxorubicin Doxorubicin Doxorubicin- semiquinone Doxorubicin Doxorubicine hydroxyaglycone Doxorubicinol hydroxyaglycone Doxorubicinol deoxaglycone Doxorubicin- semiquinone NADPH Doxorubicinol NADP NADH NAD NADH NAD NADH NAD Water Adenosine triphosphate Phosphate Adenosine diphosphate Water Adenosine triphosphate Phosphate Adenosine diphosphate Water Adenosine triphosphate Phosphate Adenosine diphosphate Water Adenosine triphosphate Phosphate Adenosine diphosphate