Farnesyl pyrophosphate
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Farnesyl pyrophosphate

Reference/ChemSpider 5960
type: UnificationXref
id: 5960
db: ChemSpider

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

Squalene monooxygenase
type: ProteinReference
xref: Reference/UniProt Q14534
organism: BiologicalState973

direct_interaction
type: InteractionVocabulary

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

Compound/PW C000143 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0001188
type: UnificationXref
id: HMDB0001188
db: HMDB

Reference/KEGG Compound C00448
type: UnificationXref
id: C00448
db: KEGG Compound

Reference/CAS 111-02-4
type: UnificationXref
id: 111-02-4
db: CAS

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

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

Reference/PathWhiz PW000050
type: UnificationXref
id: PW000050
db: PathWhiz

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

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

Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

Solute carrier family 22 member 5
type: Protein
entity reference: Solute carrier family 22 member 5

Reference/ChemSpider 559142
type: UnificationXref
id: 559142
db: ChemSpider

(S)-2,3-Epoxysqualene
type: SmallMoleculeReference
xref: Reference/BioCyc EPOXYSQUALENE
xref: Reference/CAS 9029-62-3
xref: Reference/ChemSpider 30776536
xref: Reference/PubChem-compound 53477723
xref: Reference/KEGG Compound C01054
xref: Reference/HMDB HMDB0001188
xref: Reference/ChEBI CHEBI 15441
chemical formula: C30H50O
molecular weight: 426.38617
structure: ChemicalStructure/PW C000924

Reference/ChEBI CHEBI 16113
type: UnificationXref
id: CHEBI:16113
db: ChEBI

TransportCatalysis5028
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14062
control type: ACTIVATION

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

TransportCatalysis5029
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14063
control type: ACTIVATION

TransportCatalysis5026
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14060
control type: ACTIVATION

TransportCatalysis5027
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14061
control type: ACTIVATION

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

ATP-binding cassette sub-family C member 3
type: ProteinReference
xref: Reference/UniProt O15438

Reference/ChEBI CHEBI 16474
type: UnificationXref
id: CHEBI:16474
db: ChEBI

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

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

Reference/ChEBI CHEBI 52367
type: UnificationXref
id: CHEBI:52367
db: ChEBI

TransportCatalysis5024
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14058
control type: ACTIVATION

TransportCatalysis5025
type: Catalysis
controller: ATP-binding cassette sub-family C member 3
controlled: Transport14059
control type: ACTIVATION

TransportCatalysis5022
type: Catalysis
controller: Canalicular multispecific organic anion transporter 2
controlled: Transport14056
control type: ACTIVATION

TransportCatalysis5023
type: Catalysis
controller: Solute carrier organic anion transporter family member 1B1
controlled: Transport14057
control type: ACTIVATION

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

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

(S)-2,3-Epoxysqualene
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: (S)-2,3-Epoxysqualene
name: SubPathwayInput

ChemicalStructure/PW C112989
type: ChemicalStructure
structure format: SMILES
structure data: CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12

Reference/ChEBI CHEBI 38137
type: UnificationXref
id: CHEBI:38137
db: ChEBI

Cholesterol
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Cholesterol
name: SubPathwayOutput

Reference/PubChem-compound 445713
type: UnificationXref
id: 445713
db: PubChem-compound

Compound/PW C112995 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-Naphthoic acid
stoichiometric coefficient: 1.0

ChemicalStructure/PW C112987
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)(CO)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12

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

ChemicalStructure/PW C112996
type: ChemicalStructure
structure format: SMILES
structure data: CN(C\C=C\C#CC(C)(C)C)CC1=CC(O)=C(O)C2=CC=CC=C12

ChemicalStructure/PW C112995
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)C1=C2C=CC=CC2=CC=C1

ChemicalStructure/PW C112994
type: ChemicalStructure
structure format: SMILES
structure data: CN(C\C=C\C#CC(C)(C)C(O)=O)CC1=CC=CC2=CC=CC=C12

Reference/KEGG Compound C08079
type: UnificationXref
id: C08079
db: KEGG Compound

ChemicalStructure/PW C112993
type: ChemicalStructure
structure format: SMILES
structure data: OCC1=CC=CC2=CC=CC=C12

ChemicalStructure/PW C112992
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)(C)C#C\C=C\CNCC1=CC=CC2=C(O)C(O)=CC=C12

ChemicalStructure/PW C112991
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)(C)C#C\C=C\CNCC1=CC(O)=C(O)C2=CC=CC=C12

ChemicalStructure/PW C112990
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)(CO)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12

Terbinafine dihydrodiol derivative (2)
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Terbinafine dihydrodiol derivative (2)

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

Terbinafine dihydrodiol derivative (1)
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: Terbinafine dihydrodiol derivative (1)

ChemicalStructure/PW C000924
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C

ChemicalStructure/PW C112997
type: ChemicalStructure
structure format: SMILES
structure data: CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=C(O)C(O)=CC=C12

Reference/ChEBI CHEBI 9448
type: UnificationXref
id: CHEBI:9448
db: ChEBI

Reference/ChemSpider 1266005
type: UnificationXref
id: 1266005
db: ChemSpider

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

Reference/KEGG Compound C00006
type: UnificationXref
id: C00006
db: KEGG Compound

Reference/ChEBI CHEBI 18009
type: UnificationXref
id: CHEBI:18009
db: ChEBI

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

Reference/ChEBI CHEBI 18361
type: UnificationXref
id: CHEBI:18361
db: ChEBI

Reference/KEGG Compound C00005
type: UnificationXref
id: C00005
db: KEGG Compound

Compound/PW C043234 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-Naphthaldehyde
stoichiometric coefficient: 1.0

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

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

Compound/PW C112989 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydroxyterbinafine
stoichiometric coefficient: 1.0

Reference/UniProt P37268
type: UnificationXref
id: P37268
db: UniProt

Compound/PW C112996 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Terbinafine dihydrodiol derivative (1)
stoichiometric coefficient: 1.0

Reference/CAS 57-88-5
type: UnificationXref
id: 57-88-5
db: CAS

Compound/PW C112997 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Terbinafine dihydrodiol derivative (2)
stoichiometric coefficient: 1.0

Squalene monooxygenase
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Squalene monooxygenase

Reference/KEGG Compound C00013
type: UnificationXref
id: C00013
db: KEGG Compound

Reference/BioCyc NAD(P)
type: UnificationXref
id: NAD(P)
db: BioCyc

Reaction179290
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000175 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000170 Cytoplasm/Stoichiometry/2.0
participant stoichiometry: Compound/PW C000146 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000768 Cytoplasm/Stoichiometry/2.0
right: Squalene
right: Pyrophosphate
right: NADP
spontaneous: false
left: Hydrogen Ion
left: Farnesyl pyrophosphate
left: NADPH
name: 2 Farnesyl pyrophosphate + Hydrogen Ion + NADPH → NADP + 2 Pyrophosphate + Squalene
conversion direction: LEFT_TO_RIGHT

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

Reference/ChemSpider 5775
type: UnificationXref
id: 5775
db: ChemSpider

Squalene synthase
type: ProteinReference
xref: Reference/UniProt P37268
organism: BiologicalState31

Terbinafine
type: SmallMolecule
entity reference: Terbinafine

Terbinafine
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0014995
xref: Reference/ChEBI CHEBI 9448
xref: Reference/ChemSpider 1266005
xref: Reference/KEGG Compound C08079
xref: Reference/PubChem-compound 1549008
xref: Reference/CAS 91161-71-6
chemical formula: C21H25N
molecular weight: 291.1987
structure: ChemicalStructure/PW C009312

ReactionCatalysis207809
type: Catalysis
controller: Cytochrome P450 1A2
controlled: 1.14.14.1
control type: ACTIVATION

ReactionCatalysis207808
type: Catalysis
controller: Cytochrome P450 3A4
controlled: Reaction218394
control type: ACTIVATION

ReactionCatalysis207807
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction218394
control type: ACTIVATION

Compound/PW C000170 Cytoplasm/Stoichiometry/2.0
type: Stoichiometry
physical entity: Pyrophosphate
stoichiometric coefficient: 2.0

ReactionCatalysis207806
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction218394
control type: ACTIVATION

ReactionCatalysis207805
type: Catalysis
controller: Cytochrome P450 2C8
controlled: Reaction218394
control type: ACTIVATION

ReactionCatalysis207804
type: Catalysis
controller: Cytochrome P450 2B6
controlled: Reaction218394
control type: ACTIVATION

ReactionCatalysis207803
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction218394
control type: ACTIVATION

Reference/CAS 372-97-4
type: UnificationXref
id: 372-97-4
db: CAS

ReactionCatalysis207800
type: Catalysis
controller: Cytochrome P450 1A2
controlled: 1.14.14.1
control type: ACTIVATION

ChemicalStructure/PW C000175
type: ChemicalStructure
structure format: SMILES
structure data: CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C

Reference/HMDB HMDB0000256
type: UnificationXref
id: HMDB0000256
db: HMDB

BiologicalState31
type: BioSource
xref: Reference/TAXONOMY 9606
name: Homo sapiens, Liver
tissue: Liver

Reference/HMDB HMDB0000250
type: UnificationXref
id: HMDB0000250
db: HMDB

ChemicalStructure/PW C000170
type: ChemicalStructure
structure format: SMILES
structure data: OP(O)(=O)OP(O)(O)=O

Compound/PW C112993 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-Naphthalenemethanol
stoichiometric coefficient: 1.0

ReactionCatalysis207817
type: Catalysis
controller: Cytochrome P450 3A4
controlled: Reaction218396
control type: ACTIVATION

ReactionCatalysis207816
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction218396
control type: ACTIVATION

ReactionCatalysis207815
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction218396
control type: ACTIVATION

ReactionCatalysis207814
type: Catalysis
controller: Cytochrome P450 2C8
controlled: Reaction218396
control type: ACTIVATION

ReactionCatalysis207813
type: Catalysis
controller: Cytochrome P450 2B6
controlled: Reaction218396
control type: ACTIVATION

ReactionCatalysis207812
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction218396
control type: ACTIVATION

Reference/ChemSpider 10148626
type: UnificationXref
id: 10148626
db: ChemSpider

Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Terbinafine
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0060891
type: UnificationXref
id: HMDB0060891
db: HMDB

Reference/HMDB HMDB0060890
type: UnificationXref
id: HMDB0060890
db: HMDB

Farnesyl pyrophosphate
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00448
xref: Reference/HMDB HMDB0000961
xref: Reference/ChemSpider 393270
xref: Reference/ChEBI CHEBI 17407
xref: Reference/CAS 372-97-4
xref: Reference/BioCyc FARNESYL-PP
xref: Reference/PubChem-compound 445713
chemical formula: C15H28O7P2
molecular weight: 382.13104
structure: ChemicalStructure/PW C000768

TransportCatalysis5305
type: Catalysis
controller: Solute carrier family 22 member 5
controlled: Transport14454
control type: ACTIVATION

Reference/PubChem-compound 53477723
type: UnificationXref
id: 53477723
db: PubChem-compound

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

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/CAS 9029-62-3
type: UnificationXref
id: 9029-62-3
db: CAS

Solute carrier organic anion transporter family member 1B1
type: ProteinReference
xref: Reference/UniProt Q9Y6L6

Reference/ChemSpider 10669740
type: UnificationXref
id: 10669740
db: ChemSpider

Reference/ChemSpider 10669741
type: UnificationXref
id: 10669741
db: ChemSpider

Reference/KEGG Compound C00187
type: UnificationXref
id: C00187
db: KEGG Compound

Reference/BioCyc FARNESYL-PP
type: UnificationXref
id: FARNESYL-PP
db: BioCyc

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

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

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

ChemicalStructure/PW C000047
type: ChemicalStructure
structure format: SMILES

Reference/UniProt P20813
type: UnificationXref
id: P20813
db: UniProt

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

1-Naphthaldehyde
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 52367
xref: Reference/PubChem-compound 6195
xref: Reference/ChemSpider 5960
xref: Reference/KEGG Compound C14090
xref: Reference/HMDB HMDB0060325
chemical formula: C11H8O
molecular weight: 156.05751
structure: ChemicalStructure/PW C043234

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

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

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

Compound/PW C112992 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylterbinafine dihydrodiol derivative (2)
stoichiometric coefficient: 1.0

1-Naphthaldehyde
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: 1-Naphthaldehyde

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

Compound/PW C112994/Stoichiometry/1.0
type: Stoichiometry
physical entity: Carboxyterbinafine
stoichiometric coefficient: 1.0

Compound/PW C112994 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Carboxyterbinafine
stoichiometric coefficient: 1.0

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

Reference/KEGG Compound C01054
type: UnificationXref
id: C01054
db: KEGG Compound

Reference/HMDB HMDB0000067
type: UnificationXref
id: HMDB0000067
db: HMDB

Reference/PubChem-compound 644102
type: UnificationXref
id: 644102
db: PubChem-compound

Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 2.0

Reference/PubChem-compound 22833512
type: UnificationXref
id: 22833512
db: PubChem-compound

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

Reference/HMDB HMDB0060322
type: UnificationXref
id: HMDB0060322
db: HMDB

Reference/HMDB HMDB0060325
type: UnificationXref
id: HMDB0060325
db: HMDB

Reference/PubChem-compound 6195
type: UnificationXref
id: 6195
db: PubChem-compound

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

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

Reference/ChEBI CHEBI 174203
type: UnificationXref
id: CHEBI:174203
db: ChEBI

Reference/ChemSpider 17215925
type: UnificationXref
id: 17215925
db: ChemSpider

ReactionCatalysis207769
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction218384
control type: ACTIVATION

Compound/PW C112990/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylhydroxyterbinafine
stoichiometric coefficient: 1.0

ReactionCatalysis207768
type: Catalysis
controller: Cytochrome P450 2C19
controlled: 1.14.13.-
control type: ACTIVATION

N-Desmethylterbinafine dihydrodiol derivative (1)
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: N-Desmethylterbinafine dihydrodiol derivative (1)

ReactionCatalysis207763
type: Catalysis
controller: Cytochrome P450 3A4
controlled: Reaction218382
control type: ACTIVATION

Compound/PW C112991 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylterbinafine dihydrodiol derivative (1)
stoichiometric coefficient: 1.0

ReactionCatalysis207762
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction218382
control type: ACTIVATION

ReactionCatalysis207761
type: Catalysis
controller: Cytochrome P450 2B6
controlled: Reaction218382
control type: ACTIVATION

ReactionCatalysis207760
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction218382
control type: ACTIVATION

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

Cytochrome P450 3A4
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 3A4

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

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

Cytochrome P450 3A4
type: ProteinReference
xref: Reference/UniProt P08684
organism: BiologicalState973

Cytochrome P450 2B6
type: ProteinReference
xref: Reference/UniProt P20813
organism: BiologicalState973

ReactionCatalysis207778
type: Catalysis
controller: Cytochrome P450 2C9
controlled: 1.14.13.-
control type: ACTIVATION

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

ReactionCatalysis207774
type: Catalysis
controller: Cytochrome P450 3A4
controlled: Reaction218384
control type: ACTIVATION

ReactionCatalysis207773
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction218384
control type: ACTIVATION

ReactionCatalysis207772
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction218384
control type: ACTIVATION

ReactionCatalysis207771
type: Catalysis
controller: Cytochrome P450 2C8
controlled: Reaction218384
control type: ACTIVATION

ReactionCatalysis207770
type: Catalysis
controller: Cytochrome P450 2B6
controlled: Reaction218384
control type: ACTIVATION

Reference/ChemSpider 393270
type: UnificationXref
id: 393270
db: ChemSpider

Interaction3976
type: MolecularInteraction
interaction type: direct_interaction
name: Terbinafine inhibits Squalene monooxygenase
participant: Terbinafine
participant: Squalene monooxygenase

Cholesterol
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0000067
xref: Reference/ChEBI CHEBI 16113
xref: Reference/BioCyc CHOLESTEROL
xref: Reference/KEGG Compound C00187
xref: Reference/ChemSpider 5775
xref: Reference/PubChem-compound 5997
xref: Reference/CAS 57-88-5
chemical formula: C27H46O
molecular weight: 386.35486
structure: ChemicalStructure/PW C000047

Reference/ChemSpider 19669
type: UnificationXref
id: 19669
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

Reference/CAS 53-59-8
type: UnificationXref
id: 53-59-8
db: CAS

Compound/PW C000175 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Squalene
stoichiometric coefficient: 1.0

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

Reference/PubChem-compound 5997
type: UnificationXref
id: 5997
db: PubChem-compound

Cytochrome P450 2C8
type: ProteinReference
xref: Reference/UniProt P10632
organism: BiologicalState973

Reaction218382
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112987 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine
spontaneous: false
left: Terbinafine
name: Terbinafine → N-Desmethylterbinafine
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112987 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112990 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 C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: N-Desmethylhydroxyterbinafine
right: NADP
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Oxygen
left: NADPH
left: N-Desmethylterbinafine
name: N-Desmethylterbinafine + NADPH + Oxygen → Hydrogen Ion + N-Desmethylhydroxyterbinafine + NADP + Water
conversion direction: LEFT_TO_RIGHT

Reaction218384
type: BiochemicalReaction
participant stoichiometry: Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C043234 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: 1-Naphthaldehyde
spontaneous: false
left: Terbinafine
name: Terbinafine → 1-Naphthaldehyde
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112989 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C009312 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 C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: Hydroxyterbinafine
right: NADP
right: Hydrogen Ion
spontaneous: false
EC number: 1.14.13.-
left: Oxygen
left: NADPH
left: Terbinafine
name: NADPH + Oxygen + Terbinafine → Hydrogen Ion + Hydroxyterbinafine + NADP + Water
conversion direction: LEFT_TO_RIGHT

Transport14061
type: Transport
participant stoichiometry: Compound/PW C112992/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112992 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine dihydrodiol derivative (2)
spontaneous: false
left: N-Desmethylterbinafine dihydrodiol derivative (2)
name: N-Desmethylterbinafine dihydrodiol derivative (2) (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Transport14060
type: Transport
participant stoichiometry: Compound/PW C112994 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112994/Stoichiometry/1.0
right: Carboxyterbinafine
spontaneous: false
left: Carboxyterbinafine
name: Carboxyterbinafine (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Transport14063
type: Transport
participant stoichiometry: Compound/PW C112995/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112995 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: 1-Naphthoic acid
spontaneous: false
left: 1-Naphthoic acid
name: 1-Naphthoic acid (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Transport14062
type: Transport
participant stoichiometry: Compound/PW C112993/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112993 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: 1-Naphthalenemethanol
spontaneous: false
left: 1-Naphthalenemethanol
name: 1-Naphthalenemethanol (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Compound/PW C112991/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylterbinafine dihydrodiol derivative (1)
stoichiometric coefficient: 1.0

ReactionCatalysis207759
type: Catalysis
controller: Cytochrome P450 2C8
controlled: Reaction218382
control type: ACTIVATION

ReactionCatalysis207758
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction218382
control type: ACTIVATION

Reaction218389
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112989 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112990 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylhydroxyterbinafine
spontaneous: false
left: Hydroxyterbinafine
name: Hydroxyterbinafine → N-Desmethylhydroxyterbinafine
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
participant stoichiometry: Compound/PW C112987 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112992 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
right: N-Desmethylterbinafine dihydrodiol derivative (2)
right: NADP
spontaneous: false
EC number: 1.14.14.1
left: Oxygen
left: NADPH
left: N-Desmethylterbinafine
name: N-Desmethylterbinafine + 2 NADPH + Oxygen → N-Desmethylterbinafine dihydrodiol derivative (2) + 2 NADP
conversion direction: LEFT_TO_RIGHT

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
participant stoichiometry: Compound/PW C112987 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112991 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine dihydrodiol derivative (1)
right: NADP
spontaneous: false
EC number: 1.14.13.-
left: Oxygen
left: NADPH
left: N-Desmethylterbinafine
name: N-Desmethylterbinafine + 2 NADPH + Oxygen → N-Desmethylterbinafine dihydrodiol derivative (1) + NADP
conversion direction: LEFT_TO_RIGHT

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

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

Transport14058
type: Transport
participant stoichiometry: Compound/PW C112990 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112990/Stoichiometry/1.0
right: N-Desmethylhydroxyterbinafine
spontaneous: false
left: N-Desmethylhydroxyterbinafine
name: N-Desmethylhydroxyterbinafine (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112996 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Terbinafine dihydrodiol derivative (1)
spontaneous: false
EC number: 1.14.14.1
left: Oxygen
left: Terbinafine
name: Oxygen + Terbinafine → Terbinafine dihydrodiol derivative (1)
conversion direction: LEFT_TO_RIGHT

Transport14057
type: Transport
participant stoichiometry: Compound/PW C009312/Stoichiometry/1.0
participant stoichiometry: Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Terbinafine
spontaneous: false
left: Terbinafine
name: Terbinafine (→) Transport: Homo sapiens, Blood Vessel to Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C043234 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112995 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: 1-Naphthoic acid
right: NADP
spontaneous: false
EC number: 1.14.14.1
left: Oxygen
left: 1-Naphthaldehyde
left: NADPH
left: Hydrogen Ion
name: 1-Naphthaldehyde + 2 Hydrogen Ion + NADPH + Oxygen → 1-Naphthoic acid + NADP + Water
conversion direction: LEFT_TO_RIGHT

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112994 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112989 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 C040034 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
right: Water
right: Carboxyterbinafine
spontaneous: false
EC number: 1.14.14.1
left: Oxygen
left: Hydroxyterbinafine
left: Hydrogen Ion
name: 2 Hydrogen Ion + Hydroxyterbinafine + Oxygen → Carboxyterbinafine + Water
conversion direction: LEFT_TO_RIGHT

Transport14059
type: Transport
participant stoichiometry: Compound/PW C112991/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112991 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine dihydrodiol derivative (1)
spontaneous: false
left: N-Desmethylterbinafine dihydrodiol derivative (1)
name: N-Desmethylterbinafine dihydrodiol derivative (1) (→) Transport: Homo sapiens, Liver, Hepatocyte, Endoplasmic Reticulum Membrane to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Compound/PW C112993/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-Naphthalenemethanol
stoichiometric coefficient: 1.0

1.14.13.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C043234 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112993 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: 1-Naphthalenemethanol
right: NADP
spontaneous: false
EC number: 1.14.13.-
left: 1-Naphthaldehyde
left: NADPH
name: 1-Naphthaldehyde + NADPH → 1-Naphthalenemethanol + NADP
conversion direction: LEFT_TO_RIGHT

Reaction218396
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112997 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112992 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine dihydrodiol derivative (2)
spontaneous: false
left: Terbinafine dihydrodiol derivative (2)
name: Terbinafine dihydrodiol derivative (2) → N-Desmethylterbinafine dihydrodiol derivative (2)
conversion direction: LEFT_TO_RIGHT

Compound/PW C112990 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylhydroxyterbinafine
stoichiometric coefficient: 1.0

1.14.14.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
participant stoichiometry: Compound/PW C112997 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C009312 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
right: Terbinafine dihydrodiol derivative (2)
right: NADP
spontaneous: false
EC number: 1.14.14.1
left: Oxygen
left: NADPH
left: Terbinafine
name: 2 NADPH + Oxygen + Terbinafine → 2 NADP + Terbinafine dihydrodiol derivative (2)
conversion direction: LEFT_TO_RIGHT

Transport14056
type: Transport
participant stoichiometry: Compound/PW C009312/Stoichiometry/1.0
right: Terbinafine
spontaneous: false
left: Terbinafine
name: Terbinafine (→) Transport: Homo sapiens, Intestine, Epithelial Cell to Homo sapiens, Blood Vessel
conversion direction: LEFT_TO_RIGHT

Reaction218394
type: BiochemicalReaction
participant stoichiometry: Compound/PW C112996 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C112991 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: N-Desmethylterbinafine dihydrodiol derivative (1)
spontaneous: false
left: Terbinafine dihydrodiol derivative (1)
name: Terbinafine dihydrodiol derivative (1) → N-Desmethylterbinafine dihydrodiol derivative (1)
conversion direction: LEFT_TO_RIGHT

Transport14055
type: Transport
participant stoichiometry: Compound/PW C009312/Stoichiometry/1.0
right: Terbinafine
spontaneous: true
left: Terbinafine
name: Terbinafine (→) Transport: Homo sapiens, Stomach to Homo sapiens, Intestine
conversion direction: REVERSIBLE

NADPH
type: SmallMoleculeReference
xref: Reference/CAS 53-57-6
xref: Reference/HMDB HMDB0000221
xref: Reference/PubChem-compound 22833512
xref: Reference/BioCyc NADPH
xref: Reference/ChemSpider 17215925
xref: Reference/KEGG Compound C00005
xref: Reference/ChEBI CHEBI 16474
chemical formula: C21H30N7O17P3
molecular weight: 745.0911
structure: ChemicalStructure/PW C000146

NADP
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00006
xref: Reference/CAS 53-59-8
xref: Reference/BioCyc NAD(P)
xref: Reference/HMDB HMDB0000217
xref: Reference/ChEBI CHEBI 18009
xref: Reference/PubChem-compound 5886
xref: Reference/ChemSpider 5675
chemical formula: C21H28N7O17P3
molecular weight: 743.07544
structure: ChemicalStructure/PW C000143

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

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

Reference/ChemSpider 4947262
type: UnificationXref
id: 4947262
db: ChemSpider

Compound/PW C112995/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-Naphthoic acid
stoichiometric coefficient: 1.0

Reference/ChemSpider 4947261
type: UnificationXref
id: 4947261
db: ChemSpider

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

Reference/ChEBI CHEBI 36466
type: UnificationXref
id: CHEBI:36466
db: ChEBI

Reference/HMDB HMDB0000217
type: UnificationXref
id: HMDB0000217
db: HMDB

Compound/PW C000146 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

Reference/PathWhiz PW126660
type: UnificationXref
id: PW126660
db: PathWhiz

Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 2.0

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

Reference/KEGG Compound C14091
type: UnificationXref
id: C14091
db: KEGG Compound

Reference/KEGG Compound C14090
type: UnificationXref
id: C14090
db: KEGG Compound

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

ChemicalStructure/PW C000143
type: ChemicalStructure
structure format: SMILES

Reference/HMDB HMDB0000221
type: UnificationXref
id: HMDB0000221
db: HMDB

ChemicalStructure/PW C000146
type: ChemicalStructure
structure format: SMILES

Reference/KEGG Compound C14089
type: UnificationXref
id: C14089
db: KEGG Compound

Reference/HMDB HMDB0014995
type: UnificationXref
id: HMDB0014995
db: HMDB

Reference/CAS 53-57-6
type: UnificationXref
id: 53-57-6
db: CAS

Solute carrier family 22 member 5
type: ProteinReference
xref: Reference/UniProt O76082

ReactionCatalysis207789
type: Catalysis
controller: Cytochrome P450 1A2
controlled: Reaction218389
control type: ACTIVATION

ReactionCatalysis207788
type: Catalysis
controller: Cytochrome P450 2B6
controlled: Reaction218389
control type: ACTIVATION

ReactionCatalysis207787
type: Catalysis
controller: Cytochrome P450 3A4
controlled: Reaction218389
control type: ACTIVATION

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

ReactionCatalysis207784
type: Catalysis
controller: Cytochrome P450 1A2
controlled: 1.14.14.1
control type: ACTIVATION

Pyrophosphate
type: SmallMoleculeReference
xref: Reference/PubChem-compound 644102
xref: Reference/BioCyc PPI
xref: Reference/ChemSpider 559142
xref: Reference/ChEBI CHEBI 18361
xref: Reference/HMDB HMDB0000250
xref: Reference/CAS 14000-31-8
xref: Reference/KEGG Compound C00013
chemical formula: H4O7P2
molecular weight: 177.94322
structure: ChemicalStructure/PW C000170

ReactionCatalysis207782
type: Catalysis
controller: Cytochrome P450 2B6
controlled: 1.14.13.-
control type: ACTIVATION

Solute carrier organic anion transporter family member 1B1
type: Protein
entity reference: Solute carrier organic anion transporter family member 1B1

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

Squalene
type: SmallMoleculeReference
xref: Reference/ChemSpider 10148626
xref: Reference/HMDB HMDB0000256
xref: Reference/BioCyc SQUALENE
xref: Reference/CAS 111-02-4
xref: Reference/PubChem-compound 11975273
xref: Reference/KEGG Compound C00751
xref: Reference/ChEBI CHEBI 15440
chemical formula: C30H50
molecular weight: 410.39127
structure: ChemicalStructure/PW C000175

Cytochrome P450 2B6
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2B6

Compound/PW C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

ReactionCatalysis207799
type: Catalysis
controller: Cytochrome P450 1A2
controlled: 1.14.14.1
control type: ACTIVATION

ReactionCatalysis207796
type: Catalysis
controller: Cytochrome P450 2C8
controlled: 1.14.14.1
control type: ACTIVATION

Steroid Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway117619
pathway component: SubPathwayInteraction117619
xref: Reference/SMPDB SMP0000023
xref: Reference/PathWhiz PW000050
name: SubPathway

ReactionCatalysis207793
type: Catalysis
controller: Cytochrome P450 3A4
controlled: 1.14.13.-
control type: ACTIVATION

ReactionCatalysis207792
type: Catalysis
controller: Cytochrome P450 2C19
controlled: Reaction218389
control type: ACTIVATION

Reference/UniProt O76082
type: UnificationXref
id: O76082
db: UniProt

ReactionCatalysis207791
type: Catalysis
controller: Cytochrome P450 2C8
controlled: Reaction218389
control type: ACTIVATION

ReactionCatalysis207790
type: Catalysis
controller: Cytochrome P450 2C9
controlled: Reaction218389
control type: ACTIVATION

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

Compound/PW C112992/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylterbinafine dihydrodiol derivative (2)
stoichiometric coefficient: 1.0

1.14.13.132
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000175 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000924 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 C000143 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
right: Water
right: (S)-2,3-Epoxysqualene
right: NADP
spontaneous: false
EC number: 1.14.13.132
left: Oxygen
left: Squalene
left: NADPH
name: NADPH + Oxygen + Squalene → (S)-2,3-Epoxysqualene + NADP + Water
conversion direction: LEFT_TO_RIGHT

Endoplasmic Reticulum
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005783

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

Reference/CAS 91161-71-6
type: UnificationXref
id: 91161-71-6
db: CAS

Reference/ChEBI CHEBI 15441
type: UnificationXref
id: CHEBI:15441
db: ChEBI

Reference/ChEBI CHEBI 15440
type: UnificationXref
id: CHEBI:15440
db: ChEBI

Reference/ChEBI CHEBI 173976
type: UnificationXref
id: CHEBI:173976
db: ChEBI

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

Reference/PubChem-compound 1549008
type: UnificationXref
id: 1549008
db: PubChem-compound

Reference/CAS 14000-31-8
type: UnificationXref
id: 14000-31-8
db: CAS

Compound/PW C000924 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: (S)-2,3-Epoxysqualene
stoichiometric coefficient: 1.0

Reference/ChemSpider 5675
type: UnificationXref
id: 5675
db: ChemSpider

SubPathwayInteraction117620
type: Interaction
name: SubPathway117620Reaction
name: SubPathwayReaction
participant: Carboxyterbinafine
participant: 1-Naphthalenemethanol
participant: N-Desmethylterbinafine dihydrodiol derivative (2)
participant: N-Desmethylterbinafine dihydrodiol derivative (1)
participant: N-Desmethylhydroxyterbinafine
participant: 1-Naphthoic acid

Reference/UniProt Q9Y6L6
type: UnificationXref
id: Q9Y6L6
db: UniProt

ChemicalStructure/PW C009312
type: ChemicalStructure
structure format: SMILES
structure data: CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

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

ChemicalStructure/PW C043234
type: ChemicalStructure
structure format: SMILES
structure data: O=CC1=CC=CC2=CC=CC=C12

SubPathwayInteraction117619
type: Interaction
name: SubPathwayReaction
name: SubPathway117619Reaction
participant: (S)-2,3-Epoxysqualene
participant: Cholesterol

Reference/UniProt Q14534
type: UnificationXref
id: Q14534
db: UniProt

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

Cytochrome P450 2C8
type: Protein
cellular location: Endoplasmic Reticulum Membrane
entity reference: Cytochrome P450 2C8

Homo sapiens
type: BioSource
xref: Reference/TAXONOMY 9606

1-Naphthoic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: 1-Naphthoic acid

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

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

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

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/SMPDB SMP0000023
type: UnificationXref
id: SMP0000023
db: SMPDB

Reference/GENE ONTOLOGY GO 0005783
type: UnificationXref
id: GO:0005783
db: GENE ONTOLOGY

Reference/SMPDB SMP0125122
type: UnificationXref
id: SMP0125122
db: SMPDB

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

Transport14454
type: Transport
participant stoichiometry: Compound/PW C009312/Stoichiometry/1.0
right: Terbinafine
spontaneous: false
left: Terbinafine
name: Terbinafine (→) Transport: Homo sapiens, Intestine to Homo sapiens, Intestine, Epithelial Cell
conversion direction: LEFT_TO_RIGHT

Reference/HMDB HMDB0000961
type: UnificationXref
id: HMDB0000961
db: HMDB

ATP-binding cassette sub-family C member 3
type: Protein
entity reference: ATP-binding cassette sub-family C member 3

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

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

Reference/UniProt P10632
type: UnificationXref
id: P10632
db: UniProt

Reference/KEGG Compound C00751
type: UnificationXref
id: C00751
db: KEGG Compound

ChemicalStructure/PW C000768
type: ChemicalStructure
structure format: SMILES

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

Renal excretion
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway117620
pathway component: SubPathwayInteraction117620
name: SubPathway

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

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

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+]

Reference/UniProt P08684
type: UnificationXref
id: P08684
db: UniProt

N-Desmethylterbinafine
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0060891
xref: Reference/ChEBI CHEBI 173976
xref: Reference/ChemSpider 4947261
chemical formula: C20H23NO
molecular weight: 293.17798
structure: ChemicalStructure/PW C112987

Reference/PubChem-compound 5886
type: UnificationXref
id: 5886
db: PubChem-compound

1-Naphthalenemethanol
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: 1-Naphthalenemethanol

Compound/PW C000768 Cytoplasm/Stoichiometry/2.0
type: Stoichiometry
physical entity: Farnesyl pyrophosphate
stoichiometric coefficient: 2.0

Hydroxyterbinafine
type: SmallMoleculeReference
xref: Reference/ChemSpider 10669740
xref: Reference/HMDB HMDB0060890
xref: Reference/ChEBI CHEBI 174203
chemical formula: C21H25NO
molecular weight: 307.1936
structure: ChemicalStructure/PW C112989

1-Naphthoic acid
type: SmallMolecule
entity reference: 1-Naphthoic acid
name: SubPathwayInput

N-Desmethylterbinafine dihydrodiol derivative (1)
type: SmallMoleculeReference
chemical formula: C20H23NO2
molecular weight: 309.17288
structure: ChemicalStructure/PW C112991

Carboxyterbinafine
type: SmallMolecule
entity reference: Carboxyterbinafine
name: SubPathwayInput

N-Desmethylhydroxyterbinafine
type: SmallMoleculeReference
xref: Reference/ChemSpider 10669741
chemical formula: C20H23NO
molecular weight: 293.17798
structure: ChemicalStructure/PW C112990

ReactionCatalysis169195
type: Catalysis
controller: Squalene synthase
controlled: Reaction179290
control type: ACTIVATION

1-Naphthalenemethanol
type: SmallMolecule
entity reference: 1-Naphthalenemethanol
name: SubPathwayInput

N-Desmethylterbinafine dihydrodiol derivative (2)
type: SmallMolecule
entity reference: N-Desmethylterbinafine dihydrodiol derivative (2)
name: SubPathwayInput

N-Desmethylterbinafine dihydrodiol derivative (1)
type: SmallMolecule
entity reference: N-Desmethylterbinafine dihydrodiol derivative (1)
name: SubPathwayInput

N-Desmethylhydroxyterbinafine
type: SmallMolecule
entity reference: N-Desmethylhydroxyterbinafine
name: SubPathwayInput

1-Naphthoic acid
type: SmallMoleculeReference
xref: Reference/ChemSpider 6586
xref: Reference/KEGG Compound C14091
xref: Reference/ChEBI CHEBI 36466
chemical formula: C11H8O2
molecular weight: 172.05243
structure: ChemicalStructure/PW C112995

Carboxyterbinafine
type: SmallMoleculeReference
xref: Reference/ChemSpider 4947262
chemical formula: C21H23NO2
molecular weight: 321.17288
structure: ChemicalStructure/PW C112994

Compound/PW C112987 Endoplasmic Reticulum Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N-Desmethylterbinafine
stoichiometric coefficient: 1.0

1-Naphthalenemethanol
type: SmallMoleculeReference
xref: Reference/KEGG Compound C14089
xref: Reference/ChEBI CHEBI 38137
xref: Reference/ChemSpider 19669
xref: Reference/HMDB HMDB0060322
chemical formula: C11H10O
molecular weight: 158.07317
structure: ChemicalStructure/PW C112993

N-Desmethylterbinafine dihydrodiol derivative (2)
type: SmallMoleculeReference
chemical formula: C20H23NO2
molecular weight: 309.17288
structure: ChemicalStructure/PW C112992

Squalene synthase
type: Protein
cellular location: Cytoplasm
entity reference: Squalene synthase

N-Desmethylterbinafine dihydrodiol derivative (2)
type: SmallMolecule
cellular location: Endoplasmic Reticulum Membrane
entity reference: N-Desmethylterbinafine dihydrodiol derivative (2)

ReactionCatalysis257
type: Catalysis
controller: Squalene monooxygenase
controlled: 1.14.13.132
control type: ACTIVATION

Reference/ChemSpider 30776536
type: UnificationXref
id: 30776536
db: ChemSpider

Reference/ChEBI CHEBI 17407
type: UnificationXref
id: CHEBI:17407
db: ChEBI

Terbinafine dihydrodiol derivative (2)
type: SmallMoleculeReference
chemical formula: C21H25NO2
molecular weight: 323.18854
structure: ChemicalStructure/PW C112997

Terbinafine dihydrodiol derivative (1)
type: SmallMoleculeReference
chemical formula: C21H25NO2
molecular weight: 323.18854
structure: ChemicalStructure/PW C112996

Compound/PW C000175 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Squalene
stoichiometric coefficient: 1.0

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

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

Compound/PW C009312/Stoichiometry/1.0
type: Stoichiometry
physical entity: Terbinafine
stoichiometric coefficient: 1.0

Terbinafine Metabolism
type: Pathway
pathway order: PathwayEnzymeReaction/2506305
pathway order: PathwayEnzymeReaction/2506304
pathway order: PathwayEnzymeReaction/2506307
pathway order: PathwayEnzymeReaction/2506306
pathway order: PathwayEnzymeReaction/2506309
pathway order: PathwayEnzymeReaction/2506308
pathway order: PathwayTransport/2506327
pathway order: PathwayTransport/2506326
pathway order: PathwayEnzymeReaction/2506143
pathway order: PathwayEnzymeReaction/2510653
pathway order: PathwayEnzymeReaction/2506142
pathway order: PathwayEnzymeReaction/2510654
pathway order: PathwayEnzymeReaction/2506144
pathway order: PathwayEnzymeReaction/2510650
pathway order: PathwayEnzymeReaction/2506303
pathway order: PathwayEnzymeReaction/2510652
pathway order: PathwayEnzymeReaction/2506141
pathway order: PathwayEnzymeReaction/2506140
pathway order: PathwayEnzymeReaction/2506139
pathway order: PathwayEnzymeReaction/2506297
pathway order: PathwayEnzymeReaction/2506175
pathway order: PathwayEnzymeReaction/2506296
pathway order: PathwayEnzymeReaction/2506299
pathway order: PathwayEnzymeReaction/2506298
pathway order: PathwayEnzymeReaction/2506170
pathway order: PathwayEnzymeReaction/2506172
pathway order: PathwayEnzymeReaction/2506171
pathway order: PathwayEnzymeReaction/2506174
pathway order: PathwayEnzymeReaction/2506295
pathway order: PathwayEnzymeReaction/2506173
pathway order: PathwayEnzymeReaction/2506294
pathway order: PathwayEnzymeReaction/2510639
pathway order: PathwayEnzymeReaction/2506280
pathway order: PathwayEnzymeReaction/2506282
pathway order: PathwayEnzymeReaction/2506281
pathway order: PathwayEnzymeReaction/2506283
pathway order: PathwaySubPathway/117619
pathway order: PathwayTransport/2506317
pathway order: PathwayTransport/2506315
pathway order: PathwayTransport/2506325
pathway order: PathwayEnzymeReaction/2510642
pathway order: PathwayTransport/2506324
pathway order: PathwayTransport/2506323
pathway order: PathwayEnzymeReaction/2510644
pathway order: PathwayTransport/2510657
pathway order: PathwayTransport/2506322
pathway order: PathwayTransport/2510658
pathway order: PathwayEnzymeReaction/2506279
pathway order: PathwayEnzymeReaction/2506278
pathway order: PathwayInteraction/3976
pathway order: PathwayEnzymeReaction/2506311
pathway order: PathwaySubPathway/117620
pathway order: PathwayEnzymeReaction/2510647
pathway order: PathwayEnzymeReaction/2510648
pathway component: ReactionCatalysis207809
pathway component: ReactionCatalysis207808
pathway component: ReactionCatalysis207807
pathway component: ReactionCatalysis207806
pathway component: ReactionCatalysis207805
pathway component: ReactionCatalysis207804
pathway component: ReactionCatalysis207803
pathway component: ReactionCatalysis207769
pathway component: ReactionCatalysis207768
pathway component: ReactionCatalysis207800
pathway component: ReactionCatalysis207763
pathway component: ReactionCatalysis207762
pathway component: ReactionCatalysis207761
pathway component: ReactionCatalysis207760
pathway component: Renal excretion
pathway component: ReactionCatalysis207817
pathway component: ReactionCatalysis207816
pathway component: ReactionCatalysis207815
pathway component: ReactionCatalysis207814
pathway component: ReactionCatalysis207813
pathway component: ReactionCatalysis207812
pathway component: ReactionCatalysis207778
pathway component: ReactionCatalysis207774
pathway component: ReactionCatalysis207773
pathway component: ReactionCatalysis207772

Reference/ChemSpider 6586
type: UnificationXref
id: 6586
db: ChemSpider

Compound/PW C000146 Endoplasmic Reticulum Membrane/Stoichiometry/2.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 2.0

Reference/PubChem-compound 11975273
type: UnificationXref
id: 11975273
db: PubChem-compound