Reference/ChemSpider 5309874
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id: 5309874
db: ChemSpider

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

Reference/ChEBI CHEBI 10033
type: UnificationXref
id: CHEBI:10033
db: ChEBI

Compound/PW C001294/Stoichiometry/1.0
type: Stoichiometry
physical entity: Warfarin
stoichiometric coefficient: 1.0

Reference/ChemSpider 5309875
type: UnificationXref
id: 5309875
db: ChemSpider

Compound/PW C113326 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-7-Hydroxywarfarin glucuronide
stoichiometric coefficient: 1.0

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

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

Cytochrome P450 1A2
type: ProteinReference
xref: Reference/UniProt P05177
organism: BiologicalState973

Reference/CAS 2616-64-0
type: UnificationXref
id: 2616-64-0
db: CAS

ReactionCatalysis208509
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

Solute carrier family 22 member 7
type: ProteinReference
xref: Reference/UniProt Q9Y694

Canalicular multispecific organic anion transporter 2
type: ProteinReference
xref: Reference/UniProt O15438

Reference/UniProt O15438
type: UnificationXref
id: O15438
db: UniProt

ChemicalStructure/PW C008627
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C008628
type: ChemicalStructure
structure format: SMILES

Uridine diphosphate glucuronic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Uridine diphosphate glucuronic acid

ChemicalStructure/PW C008626
type: ChemicalStructure
structure format: SMILES

R-Warfarin-R-Alcohol
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-Warfarin-R-Alcohol

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

Reference/PathWhiz PW127165
type: UnificationXref
id: PW127165
db: PathWhiz

Adenosine 3',5'-diphosphate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 17985
xref: Reference/CAS 1053-73-2
xref: Reference/PubChem-compound 159296
xref: Reference/ChemSpider 140102
xref: Reference/BioCyc 3-5-ADP
xref: Reference/KEGG Compound C00054
xref: Reference/HMDB HMDB0000061
chemical formula: C10H15N5O10P2
molecular weight: 427.02942
structure: ChemicalStructure/PW C000043

Reference/ChemSpider 10442445
type: UnificationXref
id: 10442445
db: ChemSpider

Reference/UniProt P33261
type: UnificationXref
id: P33261
db: UniProt

Reference/CELL TYPE ONTOLOGY CL 0000182
type: UnificationXref
id: CL:0000182
db: CELL TYPE ONTOLOGY

S-6-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: S-6-Hydroxywarfarin

Reference/TAXONOMY 10090
type: UnificationXref
id: 10090
db: TAXONOMY

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

Reference/KEGG Compound C01541
type: UnificationXref
id: C01541
db: KEGG Compound

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

Reference/ChEBI CHEBI 17200
type: UnificationXref
id: CHEBI:17200
db: ChEBI

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

R-7-Hydroxywarfarin glucuronide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-7-Hydroxywarfarin glucuronide

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

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

Reference/HMDB HMDB0001520
type: UnificationXref
id: HMDB0001520
db: HMDB

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

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

BiologicalState1215
type: BioSource
cell type: Hepatocyte
xref: Reference/TAXONOMY 10090
name: Mus musculus, Liver, Hepatocyte
tissue: Liver

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

Reference/ChemSpider 30776721
type: UnificationXref
id: 30776721
db: ChemSpider

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

Reference/ChemSpider 30776723
type: UnificationXref
id: 30776723
db: ChemSpider

Warfarin Metabolism
type: Pathway
pathway order: PathwayEnzymeReaction/2513060
pathway order: PathwayEnzymeReaction/2513111
pathway order: PathwayEnzymeReaction/2513188
pathway order: PathwayEnzymeReaction/2513112
pathway order: PathwayEnzymeReaction/2513186
pathway order: PathwayEnzymeReaction/2513055
pathway order: PathwayEnzymeReaction/2513187
pathway order: PathwayEnzymeReaction/2513041
pathway order: PathwayEnzymeReaction/2513042
pathway order: PathwayEnzymeReaction/2513185
pathway order: PathwayEnzymeReaction/2513094
pathway order: PathwayEnzymeReaction/2513040
pathway order: PathwayEnzymeReaction/2513051
pathway order: PathwayEnzymeReaction/2514109
pathway order: PathwayEnzymeReaction/2514108
pathway order: PathwayEnzymeReaction/2513039
pathway order: PathwayEnzymeReaction/2513169
pathway order: PathwayTransport/2513014
pathway order: PathwayTransport/2513025
pathway order: PathwayTransport/2513015
pathway component: TransportCatalysis5429
pathway component: Transport14605
pathway component: 1.14.13.-
pathway component: Transport14604
pathway component: 2.4.1.17
pathway component: Reaction219026
pathway component: Reaction219025
pathway component: Reaction219029
pathway component: Reaction219031
pathway component: ReactionCatalysis208510
pathway component: Reaction219030
pathway component: ReactionCatalysis208498
pathway component: ReactionCatalysis208497
pathway component: ReactionCatalysis208496
pathway component: Reaction219035
pathway component: ReactionCatalysis208495
pathway component: ReactionCatalysis208494
pathway component: Reaction219033
pathway component: ReactionCatalysis208493
pathway component: 2.8.2.1
pathway component: ReactionCatalysis208492
pathway component: TransportCatalysis5420
pathway component: ReactionCatalysis208491
pathway component: ReactionCatalysis208509
pathway component: Transport14616
pathway component: ReactionCatalysis208489
pathway component: ReactionCatalysis208488
pathway component: ReactionCatalysis208487
pathway component: ReactionCatalysis208486
pathway component: ReactionCatalysis208485
pathway component: ReactionCatalysis208484
pathway component: ReactionCatalysis208483
xref: Reference/SMPDB SMP0125601
xref: Reference/PathWhiz PW127165
organism: Homo sapiens

Reference/ChemSpider 30776724
type: UnificationXref
id: 30776724
db: ChemSpider

Reference/BioCyc UDP-GLUCURONATE
type: UnificationXref
id: UDP-GLUCURONATE
db: BioCyc

Reference/PubChem-compound 6031
type: UnificationXref
id: 6031
db: PubChem-compound

Reference/PubChem-compound 445395
type: UnificationXref
id: 445395
db: PubChem-compound

R-6-Hydroxywarfarin sulfate
type: SmallMolecule
cellular location: Cytosol
entity reference: R-6-Hydroxywarfarin sulfate

Transport14616
type: Transport
participant stoichiometry: Compound/PW C001294 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294/Stoichiometry/1.0
right: Warfarin
spontaneous: false
left: Warfarin
name: Warfarin (→) Transport: Homo sapiens, Blood Vessel to Homo sapiens, Liver, Hepatocyte, Cytosol
conversion direction: LEFT_TO_RIGHT

Cytochrome P450 2C9
type: ProteinReference
xref: Reference/UniProt P11712
organism: BiologicalState973

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

Cytochrome P450 2C19
type: ProteinReference
xref: Reference/UniProt P33261
organism: BiologicalState973

ChemicalStructure/PW C000201
type: ChemicalStructure
structure format: SMILES

Reference/CAS 5666-16-0
type: UnificationXref
id: 5666-16-0
db: CAS

Reference/BioCyc 3-5-ADP
type: UnificationXref
id: 3-5-ADP
db: BioCyc

Compound/PW C008632 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-7-Hydroxywarfarin
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0013883
type: UnificationXref
id: HMDB0013883
db: HMDB

Adenosine 3',5'-diphosphate
type: SmallMolecule
cellular location: Cytosol
entity reference: Adenosine 3',5'-diphosphate

Uridine diphosphate glucuronic acid
type: SmallMoleculeReference
xref: Reference/BioCyc UDP-GLUCURONATE
xref: Reference/CAS 2616-64-0
xref: Reference/PubChem-compound 17473
xref: Reference/HMDB HMDB0000935
xref: Reference/ChEBI CHEBI 17200
xref: Reference/ChemSpider 16522
xref: Reference/KEGG Compound C00167
chemical formula: C15H22N2O18P2
molecular weight: 580.0343
structure: ChemicalStructure/PW C000746

Reference/HMDB HMDB0013885
type: UnificationXref
id: HMDB0013885
db: HMDB

R-7-Hydroxywarfarin
type: SmallMolecule
cellular location: Cytosol
entity reference: R-7-Hydroxywarfarin

Reference/HMDB HMDB0013886
type: UnificationXref
id: HMDB0013886
db: HMDB

Reference/CAS 1053-73-2
type: UnificationXref
id: 1053-73-2
db: CAS

Transport14605
type: Transport
participant stoichiometry: Compound/PW C001274/Stoichiometry/1.0
right: Omeprazole
spontaneous: false
left: Omeprazole
name: Omeprazole (→) Transport: Homo sapiens, Intestine to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Transport14604
type: Transport
participant stoichiometry: Compound/PW C001274/Stoichiometry/1.0
right: Omeprazole
spontaneous: false
left: Omeprazole
name: Omeprazole (→) Transport: Homo sapiens to Homo sapiens, Intestine
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 4433
type: UnificationXref
id: 4433
db: ChemSpider

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

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

Compound/PW C001294 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Warfarin
stoichiometric coefficient: 1.0

Compound/PW C000891 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: FMNH2
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0013880
type: UnificationXref
id: HMDB0013880
db: HMDB

Reference/HMDB HMDB0013881
type: UnificationXref
id: HMDB0013881
db: HMDB

Reference/HMDB HMDB0013882
type: UnificationXref
id: HMDB0013882
db: HMDB

R-8-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-8-Hydroxywarfarin

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

Compound/PW C008626 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-6-Hydroxywarfarin
stoichiometric coefficient: 1.0

Compound/PW C001144 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADH
stoichiometric coefficient: 1.0

R-4'-Hydroxywarfarin glucuronide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-4'-Hydroxywarfarin glucuronide

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

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

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

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

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

Reference/ChemSpider 9799
type: UnificationXref
id: 9799
db: ChemSpider

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

Warfarin
type: SmallMoleculeReference
xref: Reference/CAS 81-81-2
xref: Reference/HMDB HMDB0001935
xref: Reference/KEGG Compound C01541
xref: Reference/PubChem-compound 54678486
xref: Reference/ChEBI CHEBI 10033
xref: Reference/ChemSpider 10442445
chemical formula: C19H16O4
molecular weight: 308.10486
structure: ChemicalStructure/PW C001294

Reference/ChemSpider 559060
type: UnificationXref
id: 559060
db: ChemSpider

Cytochrome P450 1A2
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 1A2

(R)9-hydroxywarfarin
type: SmallMoleculeReference

R-4'-Hydroxywarfarin glucuronide
type: SmallMoleculeReference

Warfarin
type: SmallMolecule
entity reference: Warfarin

UDP-glucuronosyltransferase 2B11
type: ProteinReference
xref: Reference/UniProt O75310
organism: BiologicalState973

Reference/PubChem-compound 17473
type: UnificationXref
id: 17473
db: PubChem-compound

Reference/PubChem-compound 159296
type: UnificationXref
id: 159296
db: PubChem-compound

Reference/PubChem-compound 54678486
type: UnificationXref
id: 54678486
db: PubChem-compound

Flavin Mononucleotide
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0001520
xref: Reference/BioCyc FMN
xref: Reference/ChemSpider 559060
xref: Reference/CAS 146-17-8
xref: Reference/ChEBI CHEBI 17621
xref: Reference/PubChem-compound 643976
xref: Reference/KEGG Compound C00061
chemical formula: C17H21N4O9P
molecular weight: 456.1046
structure: ChemicalStructure/PW C001170

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

S-7-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: S-7-Hydroxywarfarin

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

R-7-Hydroxywarfarin glucuronide
type: SmallMoleculeReference

Reference/KEGG Compound C00015
type: UnificationXref
id: C00015
db: KEGG Compound

R-7-Hydroxywarfarin sulfate
type: SmallMoleculeReference

Reference/KEGG Compound C07324
type: UnificationXref
id: C07324
db: KEGG Compound

ChemicalStructure/PW C008629
type: ChemicalStructure
structure format: SMILES

R-6-Hydroxywarfarin sulfate
type: SmallMoleculeReference

S-7-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/ChemSpider 4957014
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C113329

R-Warfarin-S-Alcohol
type: SmallMoleculeReference
chemical formula: C19H18O4
molecular weight: 310.1205
structure: ChemicalStructure/PW C113333

ReactionCatalysis208510
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

Compound/PW C113329 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-7-Hydroxywarfarin
stoichiometric coefficient: 1.0

S-Warfarin-S-Alcohol
type: SmallMoleculeReference

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

(S)9-hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/ChemSpider 57470294
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C113330

ChemicalStructure/PW C008632
type: ChemicalStructure
structure format: SMILES

R-Warfarin-R-Alcohol
type: SmallMoleculeReference
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C113331

S-Warfarin-R-Alcohol
type: SmallMoleculeReference
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C113332

ChemicalStructure/PW C008631
type: ChemicalStructure
structure format: SMILES

Reference/ChemSpider 57470294
type: UnificationXref
id: 57470294
db: ChemSpider

Hepatocyte
type: CellVocabulary
xref: Reference/CELL TYPE ONTOLOGY CL 0000182

Reference/ChEBI CHEBI 16048
type: UnificationXref
id: CHEBI:16048
db: ChEBI

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

Compound/PW C008631 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-8-Hydroxywarfarin
stoichiometric coefficient: 1.0

Reference/ChemSpider 4957014
type: UnificationXref
id: 4957014
db: ChemSpider

Reference/UniProt O75310
type: UnificationXref
id: O75310
db: UniProt

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

Omeprazole
type: SmallMoleculeReference
xref: Reference/CAS 73590-58-6
xref: Reference/PubChem-compound 4594
xref: Reference/HMDB HMDB0001913
xref: Reference/ChEBI CHEBI 77260
xref: Reference/ChemSpider 4433
xref: Reference/KEGG Compound C07324
chemical formula: C17H19N3O3S
molecular weight: 345.11472
structure: ChemicalStructure/PW C001274

Omeprazole
type: SmallMolecule
entity reference: Omeprazole

Reference/CAS 482-67-7
type: UnificationXref
id: 482-67-7
db: CAS

Reference/ChEBI CHEBI 17985
type: UnificationXref
id: CHEBI:17985
db: ChEBI

Reference/ChEBI CHEBI 17621
type: UnificationXref
id: CHEBI:17621
db: ChEBI

Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Warfarin
stoichiometric coefficient: 1.0

S-Warfarin-S-Alcohol
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: S-Warfarin-S-Alcohol

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

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000721 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113334 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: S-Warfarin-S-Alcohol
right: NAD
spontaneous: false
EC number: 1.14.13.-
left: NADH
left: Water
left: Warfarin
name: NADH + Warfarin + Water → NAD + S-Warfarin-S-Alcohol
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000721 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113333 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: R-Warfarin-S-Alcohol
right: NAD
spontaneous: false
EC number: 1.14.13.-
left: NADH
left: Water
left: Warfarin
name: NADH + Warfarin + Water → NAD + R-Warfarin-S-Alcohol
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C000721
type: ChemicalStructure
structure format: SMILES

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

Reference/ChEBI CHEBI 17980
type: UnificationXref
id: CHEBI:17980
db: ChEBI

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

ChemicalStructure/PW C001144
type: ChemicalStructure
structure format: SMILES

Compound/PW C008627 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-4'-Hydroxywarfarin
stoichiometric coefficient: 1.0

R-4'-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-4'-Hydroxywarfarin

Reference/PubChem-compound 4594
type: UnificationXref
id: 4594
db: PubChem-compound

Reference/HMDB HMDB0000935
type: UnificationXref
id: HMDB0000935
db: HMDB

Reference/KEGG Compound C00167
type: UnificationXref
id: C00167
db: KEGG Compound

ChemicalStructure/PW C001274
type: ChemicalStructure
structure format: SMILES

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

Protein/335 Cytosol/Stoichiometry/2.0
type: Stoichiometry
physical entity: Sulfotransferase 1A1
stoichiometric coefficient: 2.0

Reference/UniProt P50225
type: UnificationXref
id: P50225
db: UniProt

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

Uridine 5'-diphosphate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 17659
xref: Reference/PubChem-compound 6031
xref: Reference/CAS 58-98-0
xref: Reference/HMDB HMDB0000295
xref: Reference/KEGG Compound C00015
xref: Reference/ChemSpider 5809
xref: Reference/BioCyc UDP
chemical formula: C9H14N2O12P2
molecular weight: 404.0022
structure: ChemicalStructure/PW C000201

Compound/PW C008632 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-7-Hydroxywarfarin
stoichiometric coefficient: 1.0

R-7-Hydroxywarfarin sulfate
type: SmallMolecule
cellular location: Cytosol
entity reference: R-7-Hydroxywarfarin sulfate

R-7-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-7-Hydroxywarfarin

TransportCatalysis5429
type: Catalysis
controller: Solute carrier family 22 member 7
controlled: Transport14616
control type: ACTIVATION

Reference/PubChem-compound 643976
type: UnificationXref
id: 643976
db: PubChem-compound

Phosphoadenosine phosphosulfate
type: SmallMoleculeReference
xref: Reference/BioCyc PAPS
xref: Reference/HMDB HMDB0001134
xref: Reference/CAS 482-67-7
xref: Reference/ChemSpider 9799
xref: Reference/KEGG Compound C00053
xref: Reference/PubChem-compound 10214
xref: Reference/ChEBI CHEBI 17980
chemical formula: C10H15N5O13P2S
molecular weight: 506.98624
structure: ChemicalStructure/PW C000886

Homo sapiens
type: BioSource
xref: Reference/TAXONOMY 9606

Reference/HMDB HMDB0001913
type: UnificationXref
id: HMDB0001913
db: HMDB

Reference/ChemSpider 140102
type: UnificationXref
id: 140102
db: ChemSpider

Reference/KEGG Compound C00054
type: UnificationXref
id: C00054
db: KEGG Compound

Reference/KEGG Compound C00053
type: UnificationXref
id: C00053
db: KEGG Compound

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

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

Compound/PW C113334 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-Warfarin-S-Alcohol
stoichiometric coefficient: 1.0

Sulfotransferase 1A1
type: Complex
component stoichiometry: Protein/335 Cytosol/Stoichiometry/2.0
cellular location: Cytosol
component: Sulfotransferase 1A1

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

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

R-Warfarin-S-Alcohol
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-Warfarin-S-Alcohol

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

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

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

Reference/KEGG Compound C00061
type: UnificationXref
id: C00061
db: KEGG Compound

TransportCatalysis5420
type: Catalysis
controller: Canalicular multispecific organic anion transporter 2
controlled: Transport14605
control type: ACTIVATION

FMNH2
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16048
xref: Reference/BioCyc FMNH2
xref: Reference/KEGG Compound C01847
xref: Reference/PubChem-compound 445395
xref: Reference/CAS 5666-16-0
xref: Reference/ChemSpider 393046
xref: Reference/HMDB HMDB0001142
chemical formula: C17H23N4O9P
molecular weight: 458.12027
structure: ChemicalStructure/PW C000891

Reference/ChemSpider 16522
type: UnificationXref
id: 16522
db: ChemSpider

Reference/UniProt Q9Y694
type: UnificationXref
id: Q9Y694
db: UniProt

Reference/CAS 146-17-8
type: UnificationXref
id: 146-17-8
db: CAS

R-6-Hydroxywarfarin
type: SmallMolecule
cellular location: Cytosol
entity reference: R-6-Hydroxywarfarin

BiologicalState973
type: BioSource
cell type: Hepatocyte
xref: Reference/TAXONOMY 9606
name: Homo sapiens, Liver, Hepatocyte
tissue: Liver

Sulfotransferase 1A1
type: ProteinReference
xref: Reference/UniProt P50225
organism: BiologicalState973

Reference/PubChem-compound 10214
type: UnificationXref
id: 10214
db: PubChem-compound

(R)9-hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: (R)9-hydroxywarfarin

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

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

Reference/HMDB HMDB0001134
type: UnificationXref
id: HMDB0001134
db: HMDB

ChemicalStructure/PW C000043
type: ChemicalStructure
structure format: SMILES

Cytochrome P450 2C19
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2C19

Reference/CAS 81-81-2
type: UnificationXref
id: 81-81-2
db: CAS

Compound/PW C000746 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine diphosphate glucuronic acid
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 77260
type: UnificationXref
id: CHEBI:77260
db: ChEBI

Compound/PW C113333 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-Warfarin-S-Alcohol
stoichiometric coefficient: 1.0

Compound/PW C000043 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Adenosine 3',5'-diphosphate
stoichiometric coefficient: 1.0

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

Reference/CAS 73590-58-6
type: UnificationXref
id: 73590-58-6
db: CAS

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

Compound/PW C113328 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-6-Hydroxywarfarin sulfate
stoichiometric coefficient: 1.0

Compound/PW C000721 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NAD
stoichiometric coefficient: 1.0

Reference/KEGG Compound C01847
type: UnificationXref
id: C01847
db: KEGG Compound

Reference/HMDB HMDB0001935
type: UnificationXref
id: HMDB0001935
db: HMDB

Reference/CAS 58-98-0
type: UnificationXref
id: 58-98-0
db: CAS

R-6-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0013883
xref: Reference/ChemSpider 30776721
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008629

ChemicalStructure/PW C000886
type: ChemicalStructure
structure format: SMILES

R-4'-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0013882
xref: Reference/ChemSpider 5309875
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008628

Compound/PW C113325 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-4'-Hydroxywarfarin glucuronide
stoichiometric coefficient: 1.0

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

ChemicalStructure/PW C113329
type: ChemicalStructure
structure format: SMILES

Compound/PW C001274/Stoichiometry/1.0
type: Stoichiometry
physical entity: Omeprazole
stoichiometric coefficient: 1.0

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

ChemicalStructure/PW C000891
type: ChemicalStructure
structure format: SMILES

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

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

Compound/PW C000201 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine 5'-diphosphate
stoichiometric coefficient: 1.0

ReactionCatalysis208498
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

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

R-7-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0013886
xref: Reference/ChemSpider 30776724
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008632

ReactionCatalysis208497
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

R-8-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0013885
xref: Reference/ChemSpider 30776723
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008631

ReactionCatalysis208496
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

ReactionCatalysis208495
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction219035
control type: ACTIVATION

ChemicalStructure/PW C113333
type: ChemicalStructure
structure format: SMILES

Solute carrier family 22 member 7
type: Protein
entity reference: Solute carrier family 22 member 7

ReactionCatalysis208494
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

ChemicalStructure/PW C113332
type: ChemicalStructure
structure format: SMILES

ReactionCatalysis208493
type: Catalysis
controller: Sulfotransferase 1A1
controlled: Reaction219033
control type: ACTIVATION

ChemicalStructure/PW C113331
type: ChemicalStructure
structure format: SMILES

ReactionCatalysis208492
type: Catalysis
controller: Sulfotransferase 1A1
controlled: 2.8.2.1
control type: ACTIVATION

ChemicalStructure/PW C113330
type: ChemicalStructure
structure format: SMILES

Canalicular multispecific organic anion transporter 2
type: Protein
entity reference: Canalicular multispecific organic anion transporter 2

ReactionCatalysis208491
type: Catalysis
controller: UDP-glucuronosyltransferase 2B11
controlled: Reaction219031
control type: ACTIVATION

Reference/HMDB HMDB0001142
type: UnificationXref
id: HMDB0001142
db: HMDB

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

Reference/HMDB HMDB0000295
type: UnificationXref
id: HMDB0000295
db: HMDB

Reference/ChemSpider 5809
type: UnificationXref
id: 5809
db: ChemSpider

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

Reference/UniProt P05177
type: UnificationXref
id: P05177
db: UniProt

S-Warfarin-R-Alcohol
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: S-Warfarin-R-Alcohol

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+]

Compound/PW C008628 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-4'-Hydroxywarfarin
stoichiometric coefficient: 1.0

Reference/ChemSpider 28640819
type: UnificationXref
id: 28640819
db: ChemSpider

Compound/PW C113330 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: (S)9-hydroxywarfarin
stoichiometric coefficient: 1.0

S-4'-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: S-4'-Hydroxywarfarin

Compound/PW C113332 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-Warfarin-R-Alcohol
stoichiometric coefficient: 1.0

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008626 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: S-6-Hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + S-6-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

Reference/HMDB HMDB0000061
type: UnificationXref
id: HMDB0000061
db: HMDB

(S)9-hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: (S)9-hydroxywarfarin

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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 C008629 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: Flavin Mononucleotide
right: R-6-Hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + R-6-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

2.4.1.17
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000201 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008628 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000746 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113325 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Uridine 5'-diphosphate
right: R-4'-Hydroxywarfarin glucuronide
right: Hydrogen Ion
spontaneous: false
EC number: 2.4.1.17
left: R-4'-Hydroxywarfarin
left: Uridine diphosphate glucuronic acid
name: R-4'-Hydroxywarfarin + Uridine diphosphate glucuronic acid → Hydrogen Ion + R-4'-Hydroxywarfarin glucuronide + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

Compound/PW C008629 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-6-Hydroxywarfarin
stoichiometric coefficient: 1.0

Reaction219026
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008628 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: R-4'-Hydroxywarfarin
right: Flavin Mononucleotide
right: Hydrogen Ion
spontaneous: false
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + R-4'-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

FMNH2
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: FMNH2

Reaction219025
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008627 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: S-4'-Hydroxywarfarin
right: Water
right: Flavin Mononucleotide
right: Hydrogen Ion
spontaneous: false
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + S-4'-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

Sulfotransferase 1A1
type: Protein
cellular location: Cytosol
entity reference: Sulfotransferase 1A1

R-6-Hydroxywarfarin
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: R-6-Hydroxywarfarin

ChemicalStructure/PW C000746
type: ChemicalStructure
structure format: SMILES

Reaction219029
type: BiochemicalReaction
participant stoichiometry: Compound/PW C008631 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: R-8-Hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + R-8-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

Reaction219031
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000201 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113326 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000746 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008632 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Uridine 5'-diphosphate
right: R-7-Hydroxywarfarin glucuronide
right: Hydrogen Ion
spontaneous: false
left: Uridine diphosphate glucuronic acid
left: R-7-Hydroxywarfarin
name: R-7-Hydroxywarfarin + Uridine diphosphate glucuronic acid → Hydrogen Ion + R-7-Hydroxywarfarin glucuronide + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

Reference/BioCyc FMNH2
type: UnificationXref
id: FMNH2
db: BioCyc

Reaction219030
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008632 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
right: Water
right: Flavin Mononucleotide
right: R-7-Hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + R-7-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

UDP-glucuronosyltransferase 2B11
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: UDP-glucuronosyltransferase 2B11

Reaction219035
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113324 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: (R)9-hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → (R)9-hydroxywarfarin + Flavin Mononucleotide + Hydrogen Ion + Water
conversion direction: LEFT_TO_RIGHT

Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Flavin Mononucleotide
stoichiometric coefficient: 1.0

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

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C113329 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: S-7-Hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + S-7-Hydroxywarfarin + Water
conversion direction: LEFT_TO_RIGHT

Reaction219033
type: BiochemicalReaction
participant stoichiometry: Compound/PW C113328 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008629 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000043 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000886 Cytosol/Stoichiometry/1.0
right: Adenosine 3',5'-diphosphate
right: Hydrogen Ion
right: R-6-Hydroxywarfarin sulfate
spontaneous: false
left: Phosphoadenosine phosphosulfate
left: R-6-Hydroxywarfarin
name: Phosphoadenosine phosphosulfate + R-6-Hydroxywarfarin → Adenosine 3',5'-diphosphate + Hydrogen Ion + R-6-Hydroxywarfarin sulfate
conversion direction: LEFT_TO_RIGHT

2.8.2.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C113327 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000043 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008632 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000886 Cytosol/Stoichiometry/1.0
right: Adenosine 3',5'-diphosphate
right: Hydrogen Ion
right: R-7-Hydroxywarfarin sulfate
spontaneous: false
EC number: 2.8.2.1
left: R-7-Hydroxywarfarin
left: Phosphoadenosine phosphosulfate
name: Phosphoadenosine phosphosulfate + R-7-Hydroxywarfarin → Adenosine 3',5'-diphosphate + Hydrogen Ion + R-7-Hydroxywarfarin sulfate
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 393046
type: UnificationXref
id: 393046
db: ChemSpider

Uridine 5'-diphosphate
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Uridine 5'-diphosphate

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

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

Flavin Mononucleotide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Flavin Mononucleotide

Reference/SMPDB SMP0125601
type: UnificationXref
id: SMP0125601
db: SMPDB

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

Reference/ChEBI CHEBI 17659
type: UnificationXref
id: CHEBI:17659
db: ChEBI

Compound/PW C113331 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-Warfarin-R-Alcohol
stoichiometric coefficient: 1.0

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

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C113332 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: S-Warfarin-R-Alcohol
right: Flavin Mononucleotide
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + S-Warfarin-R-Alcohol + Water
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113331 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: R-Warfarin-R-Alcohol
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → Flavin Mononucleotide + Hydrogen Ion + R-Warfarin-R-Alcohol + Water
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001294 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001170 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C113330 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 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
right: Water
right: Flavin Mononucleotide
right: (S)9-hydroxywarfarin
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Warfarin
left: Oxygen
left: FMNH2
name: FMNH2 + Oxygen + Warfarin → (S)9-hydroxywarfarin + Flavin Mononucleotide + Hydrogen Ion + Water
conversion direction: LEFT_TO_RIGHT

Compound/PW C008629 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-6-Hydroxywarfarin
stoichiometric coefficient: 1.0

ReactionCatalysis208489
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction219030
control type: ACTIVATION

ReactionCatalysis208488
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction219029
control type: ACTIVATION

ReactionCatalysis208487
type: Catalysis
controller: Cytochrome P450 2C19
controlled: 1.14.13.-
control type: ACTIVATION

Compound/PW C113327 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: R-7-Hydroxywarfarin sulfate
stoichiometric coefficient: 1.0

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

ReactionCatalysis208486
type: Catalysis
controller: UDP-glucuronosyltransferase 2B11
controlled: 2.4.1.17
control type: ACTIVATION

ReactionCatalysis208485
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction219026
control type: ACTIVATION

ReactionCatalysis208484
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction219025
control type: ACTIVATION

S-4'-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/ChemSpider 5309874
xref: Reference/HMDB HMDB0013881
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008627

ReactionCatalysis208483
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

S-6-Hydroxywarfarin
type: SmallMoleculeReference
xref: Reference/ChemSpider 28640819
xref: Reference/HMDB HMDB0013880
chemical formula: C19H16O5
molecular weight: 324.09976
structure: ChemicalStructure/PW C008626

Phosphoadenosine phosphosulfate
type: SmallMolecule
cellular location: Cytosol
entity reference: Phosphoadenosine phosphosulfate

Compound/PW C113324 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: (R)9-hydroxywarfarin
stoichiometric coefficient: 1.0

ChemicalStructure/PW C001294
type: ChemicalStructure
structure format: SMILES

Compound/PW C000886 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phosphoadenosine phosphosulfate
stoichiometric coefficient: 1.0

ChemicalStructure/PW C001170
type: ChemicalStructure
structure format: SMILES