Reference/CAS 7722-84-1
type: UnificationXref
id: 7722-84-1
db: CAS

Cytochrome P450 2D6
type: ProteinReference
xref: Reference/UniProt P10635
organism: BiologicalState13

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

Reference/ChEBI CHEBI 16134
type: UnificationXref
id: CHEBI:16134
db: ChEBI

Reference/HMDB HMDB0003125
type: UnificationXref
id: HMDB0003125
db: HMDB

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

Compound/PW C008696 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylcitalopram
stoichiometric coefficient: 1.0

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

ChemicalStructure/PW C001783
type: ChemicalStructure
structure format: SMILES
structure data: OO

Ammonia
type: SmallMoleculeReference
xref: Reference/BioCyc AMMONIA
xref: Reference/CAS 7664-41-7
xref: Reference/HMDB HMDB0000051
xref: Reference/PubChem-compound 222
xref: Reference/KEGG Compound C00014
xref: Reference/ChEBI CHEBI 16134
xref: Reference/ChemSpider 217
chemical formula: H3N
molecular weight: 17.026548
structure: ChemicalStructure/PW C000035

Citalopram inhibition of Sodium-dependent serotonin transporter
type: Pathway
name: InhibitorySubPathway

Reference/UniProt P31645
type: UnificationXref
id: P31645
db: UniProt

Cytochrome P450 3A7
type: ProteinReference
xref: Reference/UniProt P24462
organism: BiologicalState13

Reference/HMDB HMDB0014021
type: UnificationXref
id: HMDB0014021
db: HMDB

Amine oxidase [flavin-containing] B
type: ProteinReference
xref: Reference/UniProt P27338
organism: BiologicalState13

Ammonia
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Ammonia

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

Reference/PathWhiz PW000603
type: UnificationXref
id: PW000603
db: PathWhiz

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

Citalopram propionic acid
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Citalopram propionic acid

Reference/CAS 62498-67-3
type: UnificationXref
id: 62498-67-3
db: CAS

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

Reference/KEGG Compound C00218
type: UnificationXref
id: C00218
db: KEGG Compound

Citalopram propionic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0060463
xref: Reference/ChemSpider 8578612
xref: Reference/PubChem-compound 10403174
xref: Reference/KEGG Compound C16610
chemical formula: C18H14FNO3
molecular weight: 311.09576
structure: ChemicalStructure/PW C040620

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

Reference/UniProt P24462
type: UnificationXref
id: P24462
db: UniProt

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

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

1.4.3.4
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001065 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040544 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001783 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040559 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000035 Mitochondrion/Stoichiometry/1.0
right: Ammonia
right: Citalopram aldehyde
right: Hydrogen peroxide
spontaneous: false
EC number: 1.4.3.4
left: Didemethylcitalopram
left: Water
left: Oxygen
name: Didemethylcitalopram + Oxygen + Water → Ammonia + Citalopram aldehyde + Hydrogen peroxide
conversion direction: LEFT_TO_RIGHT

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

Compound/PW C002381 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram
stoichiometric coefficient: 1.0

Formaldehyde
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16842
xref: Reference/BioCyc FORMALDEHYDE
xref: Reference/HMDB HMDB0001426
xref: Reference/PubChem-compound 712
xref: Reference/ChemSpider 692
xref: Reference/KEGG Compound C00067
xref: Reference/CAS 50-00-0
chemical formula: CH2O
molecular weight: 30.010565
structure: ChemicalStructure/PW C001102

Compound/PW C040559 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Didemethylcitalopram
stoichiometric coefficient: 1.0

Amine oxidase [flavin-containing] A
type: ProteinReference
xref: Reference/UniProt P21397
organism: BiologicalState13

Compound/PW C001102 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Formaldehyde
stoichiometric coefficient: 1.0

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

Amine oxidase [flavin-containing] A
type: Protein
cellular location: Mitochondrion
entity reference: Amine oxidase [flavin-containing] A

Citalopram N-oxide
type: SmallMoleculeReference
xref: Reference/KEGG Compound C16607
xref: Reference/PubChem-compound 10068142
xref: Reference/ChemSpider 8243682
xref: Reference/HMDB HMDB0060654
chemical formula: C20H21FN2O2
molecular weight: 340.1587
structure: ChemicalStructure/PW C040514

Reference/ChEBI CHEBI 16240
type: UnificationXref
id: CHEBI:16240
db: ChEBI

Reference/ChemSpider 8243682
type: UnificationXref
id: 8243682
db: ChemSpider

Compound/PW C000035 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Ammonia
stoichiometric coefficient: 1.0

Cytochrome P450 2C19
type: ProteinReference
xref: Reference/UniProt P33261
organism: BiologicalState13

Compound/PW C040620 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram propionic acid
stoichiometric coefficient: 1.0

Mitochondrion
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005739

Reference/PubChem-compound 9944000
type: UnificationXref
id: 9944000
db: PubChem-compound

Cytochrome P450 3A7
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 3A7

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

ChemicalStructure/PW C040544
type: ChemicalStructure
structure format: SMILES

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

Reference/ChemSpider 217
type: UnificationXref
id: 217
db: ChemSpider

Compound/PW C000060 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Dimethylamine
stoichiometric coefficient: 1.0

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

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

ChemicalStructure/PW C001102
type: ChemicalStructure
structure format: SMILES
structure data: C=O

Reference/HMDB HMDB0001426
type: UnificationXref
id: HMDB0001426
db: HMDB

Reference/ChemSpider 692
type: UnificationXref
id: 692
db: ChemSpider

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

Reference/GENE ONTOLOGY GO 0005886
type: UnificationXref
id: GO:0005886
db: GENE ONTOLOGY

BiologicalState73
type: BioSource
cell type: Neuron
xref: Reference/TAXONOMY 9606
name: Homo sapiens, Neuron

Reference/CAS 59729-33-8
type: UnificationXref
id: 59729-33-8
db: CAS

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

Reference/PubChem-compound 674
type: UnificationXref
id: 674
db: PubChem-compound

Reference/CAS 62498-69-5
type: UnificationXref
id: 62498-69-5
db: CAS

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

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

Sodium-dependent serotonin transporter
type: Protein
cellular location: Cell Membrane
entity reference: Sodium-dependent serotonin transporter
name: SubPathwayInhibition

ChemicalStructure/PW C040559
type: ChemicalStructure
structure format: SMILES
structure data: NCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

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

Reference/PubChem-compound 2771
type: UnificationXref
id: 2771
db: PubChem-compound

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

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

Compound/PW C001065 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
stoichiometric coefficient: 1.0

Reaction2010
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001783 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040544 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040620 Cytoplasm/Stoichiometry/1.0
right: Hydrogen peroxide
right: Citalopram propionic acid
spontaneous: false
left: Oxygen
left: Citalopram aldehyde
left: Water
name: Citalopram aldehyde + Oxygen + Water → Citalopram propionic acid + Hydrogen peroxide
conversion direction: LEFT_TO_RIGHT

Reference/CAS 7664-41-7
type: UnificationXref
id: 7664-41-7
db: CAS

Citalopram
type: SmallMolecule
entity reference: Citalopram
name: SubPathwayInhibitor

Citalopram
type: SmallMoleculeReference
xref: Reference/ChemSpider 2669
xref: Reference/KEGG Compound C07572
xref: Reference/ChEBI CHEBI 77397
xref: Reference/HMDB HMDB0005038
xref: Reference/CAS 59729-33-8
xref: Reference/PubChem-compound 2771
chemical formula: C20H21FN2O
molecular weight: 324.1638
structure: ChemicalStructure/PW C002381

Compound/PW C040712 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Methylammonium
stoichiometric coefficient: 1.0

Reference/SMPDB SMP0000627
type: UnificationXref
id: SMP0000627
db: SMPDB

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

Reference/ChEBI CHEBI 16830
type: UnificationXref
id: CHEBI:16830
db: ChEBI

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/CELL TYPE ONTOLOGY CL 0000540
type: UnificationXref
id: CL:0000540
db: CELL TYPE ONTOLOGY

Reference/ChEBI CHEBI 586865
type: UnificationXref
id: CHEBI:586865
db: ChEBI

Neuron
type: CellVocabulary
xref: Reference/CELL TYPE ONTOLOGY CL 0000540

Reference/HMDB HMDB0060291
type: UnificationXref
id: HMDB0060291
db: HMDB

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

Reference/PubChem-compound 10403174
type: UnificationXref
id: 10403174
db: PubChem-compound

Reference/PubChem-compound 222
type: UnificationXref
id: 222
db: PubChem-compound

Oxygen
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Oxygen

Reference/KEGG Compound C00014
type: UnificationXref
id: C00014
db: KEGG Compound

Methylammonium
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Methylammonium

SubPathwayControl529
type: Interaction
name: InhibitorySubPathwayControl
name: SubPathway529Control
participant: Citalopram inhibition of Sodium-dependent serotonin transporter
participant: Sodium-dependent serotonin transporter
participant: Citalopram

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

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

Reference/UniProt P21397
type: UnificationXref
id: P21397
db: UniProt

Reference/KEGG Compound C07572
type: UnificationXref
id: C07572
db: KEGG Compound

Aldehyde oxidase
type: ProteinReference
xref: Reference/UniProt Q06278
organism: BiologicalState13

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

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001783 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002381 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040514 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: Hydrogen peroxide
right: Citalopram N-oxide
spontaneous: false
EC number: 1.14.14.1
left: Citalopram
left: Water
left: Oxygen
name: Citalopram + Oxygen + Water → Citalopram N-oxide + Hydrogen peroxide
conversion direction: LEFT_TO_RIGHT

N-Desmethylcitalopram
type: SmallMoleculeReference
xref: Reference/KEGG Compound C16608
xref: Reference/ChemSpider 142424
xref: Reference/PubChem-compound 162180
xref: Reference/ChEBI CHEBI 586865
xref: Reference/HMDB HMDB0014021
xref: Reference/CAS 62498-67-3
chemical formula: C19H19FN2O
molecular weight: 310.14813
structure: ChemicalStructure/PW C008696

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

Sodium-dependent serotonin transporter
type: ProteinReference
xref: Reference/UniProt P31645
organism: BiologicalState73

Reference/ChEBI CHEBI 16842
type: UnificationXref
id: CHEBI:16842
db: ChEBI

Methylammonium
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00218
xref: Reference/ChEBI CHEBI 16830
xref: Reference/CAS 74-89-5
xref: Reference/PubChem-compound 6329
xref: Reference/HMDB HMDB0060291
xref: Reference/ChemSpider 6089
chemical formula: CH5N
molecular weight: 31.0422
structure: ChemicalStructure/PW C040712

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

Reference/KEGG Compound C00027
type: UnificationXref
id: C00027
db: KEGG Compound

Reference/KEGG Compound C16609
type: UnificationXref
id: C16609
db: KEGG Compound

Dimethylamine
type: SmallMoleculeReference
xref: Reference/ChemSpider 654
xref: Reference/PubChem-compound 674
xref: Reference/ChEBI CHEBI 17170
xref: Reference/KEGG Compound C00543
xref: Reference/HMDB HMDB0000087
xref: Reference/CAS 124-40-3
xref: Reference/BioCyc DIMETHYLAMINE
chemical formula: C2H7N
molecular weight: 45.05785
structure: ChemicalStructure/PW C000060

Reference/GENE ONTOLOGY GO 0005739
type: UnificationXref
id: GO:0005739
db: GENE ONTOLOGY

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

Reference/KEGG Compound C16607
type: UnificationXref
id: C16607
db: KEGG Compound

Reference/KEGG Compound C16608
type: UnificationXref
id: C16608
db: KEGG Compound

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

ChemicalStructure/PW C040620
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

Reference/CAS 74-89-5
type: UnificationXref
id: 74-89-5
db: CAS

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

ReactionCatalysis1719
type: Catalysis
controller: Cytochrome P450 2D6
controlled: 1.14.14.1
control type: ACTIVATION

ChemicalStructure/PW C000721
type: ChemicalStructure
structure format: SMILES

Cytochrome P450 2D6
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2D6

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

Didemethylcitalopram
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Didemethylcitalopram

ChemicalStructure/PW C001144
type: ChemicalStructure
structure format: SMILES

ReactionCatalysis1720
type: Catalysis
controller: Cytochrome P450 3A7
controlled: 1.14.14.1
control type: ACTIVATION

1.4.3.4
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001065 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040544 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001783 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002381 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000060 Mitochondrion/Stoichiometry/1.0
right: Citalopram aldehyde
right: Hydrogen peroxide
right: Dimethylamine
spontaneous: false
EC number: 1.4.3.4
left: Water
left: Citalopram
left: Oxygen
name: Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxide
conversion direction: LEFT_TO_RIGHT

Compound/PW C001783 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen peroxide
stoichiometric coefficient: 1.0

Reference/ChemSpider 654
type: UnificationXref
id: 654
db: ChemSpider

ReactionCatalysis1721
type: Catalysis
controller: Cytochrome P450 2C19
controlled: 1.14.14.1
control type: ACTIVATION

ReactionCatalysis1724
type: Catalysis
controller: Amine oxidase [flavin-containing] A
controlled: 1.4.3.4
control type: ACTIVATION

Reference/BioCyc HYDROGEN-PEROXIDE
type: UnificationXref
id: HYDROGEN-PEROXIDE
db: BioCyc

ReactionCatalysis1725
type: Catalysis
controller: Amine oxidase [flavin-containing] B
controlled: 1.4.3.4
control type: ACTIVATION

Reference/KEGG Compound C16612
type: UnificationXref
id: C16612
db: KEGG Compound

ChemicalStructure/PW C008696
type: ChemicalStructure
structure format: SMILES
structure data: CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

1.4.3.4
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001065 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008696 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040544 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001783 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040712 Mitochondrion/Stoichiometry/1.0
right: Citalopram aldehyde
right: Hydrogen peroxide
right: Methylammonium
spontaneous: false
EC number: 1.4.3.4
left: Water
left: N-Desmethylcitalopram
left: Oxygen
name: N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Hydrogen peroxide + Methylammonium
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000721 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002381 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008696 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001102 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: Formaldehyde
right: NAD
right: N-Desmethylcitalopram
spontaneous: false
EC number: 1.14.14.1
left: Citalopram
left: NADH
left: Oxygen
name: Citalopram + NADH + Oxygen → Formaldehyde + N-Desmethylcitalopram + NAD + Water
conversion direction: LEFT_TO_RIGHT

Reference/KEGG Compound C16610
type: UnificationXref
id: C16610
db: KEGG Compound

ChemicalStructure/PW C040514
type: ChemicalStructure
structure format: SMILES
structure data: CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

Compound/PW C008696 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylcitalopram
stoichiometric coefficient: 1.0

Reference/ChemSpider 6089
type: UnificationXref
id: 6089
db: ChemSpider

Amine oxidase [flavin-containing] B
type: Protein
cellular location: Mitochondrion
entity reference: Amine oxidase [flavin-containing] B

Reference/ChemSpider 763
type: UnificationXref
id: 763
db: ChemSpider

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

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

Reference/HMDB HMDB0005038
type: UnificationXref
id: HMDB0005038
db: HMDB

ChemicalStructure/PW C000060
type: ChemicalStructure
structure format: SMILES
structure data: CNC

Compound/PW C040544 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram aldehyde
stoichiometric coefficient: 1.0

Reference/PubChem-compound 784
type: UnificationXref
id: 784
db: PubChem-compound

Homo sapiens
type: BioSource
xref: Reference/TAXONOMY 9606

Reference/PubChem-compound 162976
type: UnificationXref
id: 162976
db: PubChem-compound

ReactionCatalysis1859
type: Catalysis
controller: Amine oxidase [flavin-containing] A
controlled: 1.4.3.4
control type: ACTIVATION

Reference/PubChem-compound 6329
type: UnificationXref
id: 6329
db: PubChem-compound

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

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

Dimethylamine
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Dimethylamine

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

ReactionCatalysis1742
type: Catalysis
controller: Cytochrome P450 2D6
controlled: 1.14.14.1
control type: ACTIVATION

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/ChEBI CHEBI 77397
type: UnificationXref
id: CHEBI:77397
db: ChEBI

ReactionCatalysis1866
type: Catalysis
controller: Aldehyde oxidase
controlled: Reaction2010
control type: ACTIVATION

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

ChemicalStructure/PW C000035
type: ChemicalStructure
structure format: SMILES
structure data: N

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

Reference/PubChem-compound 10068142
type: UnificationXref
id: 10068142
db: PubChem-compound

Reference/UniProt P27338
type: UnificationXref
id: P27338
db: UniProt

ReactionCatalysis1860
type: Catalysis
controller: Amine oxidase [flavin-containing] B
controlled: 1.4.3.4
control type: ACTIVATION

BiologicalState13
type: BioSource
xref: Reference/TAXONOMY 9606
name: Homo sapiens, Liver
tissue: Liver

Compound/PW C040514 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram N-oxide
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00067
type: UnificationXref
id: C00067
db: KEGG Compound

N-Desmethylcitalopram
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: N-Desmethylcitalopram

Aldehyde oxidase
type: Protein
cellular location: Cytoplasm
entity reference: Aldehyde oxidase

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

Reference/CAS 124-40-3
type: UnificationXref
id: 124-40-3
db: CAS

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

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

Reference/ChEBI CHEBI 17170
type: UnificationXref
id: CHEBI:17170
db: ChEBI

Citalopram aldehyde
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Citalopram aldehyde

Compound/PW C001065 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
stoichiometric coefficient: 1.0

Compound/PW C040544 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram aldehyde
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0060654
type: UnificationXref
id: HMDB0060654
db: HMDB

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

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

Reference/UniProt P10635
type: UnificationXref
id: P10635
db: UniProt

Compound/PW C001783 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen peroxide
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0060472
type: UnificationXref
id: HMDB0060472
db: HMDB

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

Reference/ChemSpider 143072
type: UnificationXref
id: 143072
db: ChemSpider

Citalopram Metabolism Pathway
type: Pathway
pathway order: PathwayEnzymeReaction/3452
pathway order: PathwayEnzymeReaction/3453
pathway order: PathwaySubPathway/529
pathway order: PathwayEnzymeReaction/3454
pathway order: PathwayEnzymeReaction/3444
pathway order: PathwayEnzymeReaction/3455
pathway order: PathwayEnzymeReaction/3450
pathway order: PathwayEnzymeReaction/3451
pathway order: PathwayEnzymeReaction/3449
pathway order: PathwayEnzymeReaction/3445
pathway order: PathwayEnzymeReaction/3446
pathway order: PathwayEnzymeReaction/3447
pathway order: PathwayEnzymeReaction/3448
pathway component: 1.14.14.1
pathway component: ReactionCatalysis1859
pathway component: ReactionCatalysis1719
pathway component: SubPathwayControl529
pathway component: ReactionCatalysis1720
pathway component: ReactionCatalysis1742
pathway component: 1.4.3.4
pathway component: Reaction2010
pathway component: ReactionCatalysis1721
pathway component: ReactionCatalysis1724
pathway component: ReactionCatalysis1701
pathway component: ReactionCatalysis1866
pathway component: ReactionCatalysis1715
pathway component: ReactionCatalysis1714
pathway component: ReactionCatalysis1725
pathway component: ReactionCatalysis1860
xref: Reference/SMPDB SMP0000627
xref: Reference/PathWhiz PW000603
organism: Homo sapiens

N-Desmethylcitalopram
type: SmallMolecule
cellular location: Mitochondrion
entity reference: N-Desmethylcitalopram

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

Reference/ChemSpider 142424
type: UnificationXref
id: 142424
db: ChemSpider

Compound/PW C001783 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen peroxide
stoichiometric coefficient: 1.0

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

Reference/ChemSpider 8119612
type: UnificationXref
id: 8119612
db: ChemSpider

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

Citalopram N-oxide
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Citalopram N-oxide

Hydrogen peroxide
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Hydrogen peroxide

Reference/HMDB HMDB0000051
type: UnificationXref
id: HMDB0000051
db: HMDB

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

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

Cell Membrane
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005886

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

ChemicalStructure/PW C040712
type: ChemicalStructure
structure format: SMILES
structure data: CN

Reference/PubChem-compound 712
type: UnificationXref
id: 712
db: PubChem-compound

Reference/UniProt Q06278
type: UnificationXref
id: Q06278
db: UniProt

Compound/PW C002381 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Citalopram
stoichiometric coefficient: 1.0

Reference/ChemSpider 8578612
type: UnificationXref
id: 8578612
db: ChemSpider

Reference/PubChem-compound 162180
type: UnificationXref
id: 162180
db: PubChem-compound

Citalopram aldehyde
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0060462
xref: Reference/ChemSpider 8119612
xref: Reference/KEGG Compound C16612
xref: Reference/PubChem-compound 9944000
chemical formula: C18H14FNO2
molecular weight: 295.10086
structure: ChemicalStructure/PW C040544

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000721 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008696 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040559 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001102 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: Formaldehyde
right: Didemethylcitalopram
right: NAD
spontaneous: false
EC number: 1.14.14.1
left: NADH
left: Oxygen
left: N-Desmethylcitalopram
name: N-Desmethylcitalopram + NADH + Oxygen → Didemethylcitalopram + Formaldehyde + NAD + Water
conversion direction: LEFT_TO_RIGHT

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

Hydrogen peroxide
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0003125
xref: Reference/PubChem-compound 784
xref: Reference/ChemSpider 763
xref: Reference/CAS 7722-84-1
xref: Reference/BioCyc HYDROGEN-PEROXIDE
xref: Reference/ChEBI CHEBI 16240
xref: Reference/KEGG Compound C00027
chemical formula: H2O2
molecular weight: 34.005478
structure: ChemicalStructure/PW C001783

ReactionCatalysis1701
type: Catalysis
controller: Cytochrome P450 2D6
controlled: 1.14.14.1
control type: ACTIVATION

Citalopram aldehyde
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Citalopram aldehyde

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

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

Reference/HMDB HMDB0060462
type: UnificationXref
id: HMDB0060462
db: HMDB

Reference/ChemSpider 2669
type: UnificationXref
id: 2669
db: ChemSpider

Reference/HMDB HMDB0060463
type: UnificationXref
id: HMDB0060463
db: HMDB

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

Didemethylcitalopram
type: SmallMoleculeReference
xref: Reference/KEGG Compound C16609
xref: Reference/HMDB HMDB0060472
xref: Reference/CAS 62498-69-5
xref: Reference/ChemSpider 143072
xref: Reference/PubChem-compound 162976
chemical formula: C18H17FN2O
molecular weight: 296.13248
structure: ChemicalStructure/PW C040559

Compound/PW C040559 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Didemethylcitalopram
stoichiometric coefficient: 1.0

Reference/CAS 50-00-0
type: UnificationXref
id: 50-00-0
db: CAS

Citalopram
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Citalopram

Reference/KEGG Compound C00543
type: UnificationXref
id: C00543
db: KEGG Compound

ReactionCatalysis1715
type: Catalysis
controller: Amine oxidase [flavin-containing] B
controlled: 1.4.3.4
control type: ACTIVATION

ReactionCatalysis1714
type: Catalysis
controller: Amine oxidase [flavin-containing] A
controlled: 1.4.3.4
control type: ACTIVATION

ChemicalStructure/PW C002381
type: ChemicalStructure
structure format: SMILES
structure data: CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

Reference/HMDB HMDB0000087
type: UnificationXref
id: HMDB0000087
db: HMDB

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