Reference/ChEBI CHEBI 16015
type: UnificationXref
id: CHEBI:16015
db: ChEBI

ReactionCatalysis169608
type: Catalysis
controller: Tat protein
controlled: 2.6.1.1
control type: ACTIVATION

Reference/PubChem-compound 11970
type: UnificationXref
id: 11970
db: PubChem-compound

ReactionCatalysis169607
type: Catalysis
controller: Aspartate aminotransferase
controlled: 2.6.1.1
control type: ACTIVATION

Reference/ChemSpider 30572
type: UnificationXref
id: 30572
db: ChemSpider

ReactionCatalysis169606
type: Catalysis
controller: Amine oxidase
controlled: 1.4.3.-
control type: ACTIVATION

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

Reference/PubChem-compound 6140
type: UnificationXref
id: 6140
db: PubChem-compound

Reaction180212
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000131/Stoichiometry/1.0
participant stoichiometry: Compound/PW C007772/Stoichiometry/1.0
right: Enol-phenylpyruvate
spontaneous: false
left: Phenylpyruvic acid
name: Phenylpyruvic acid ↔ Enol-phenylpyruvate
conversion direction: REVERSIBLE

Reaction180211
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000131/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001316/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000526/Stoichiometry/1.0
right: Carbon dioxide
right: ortho-Hydroxyphenylacetic acid
spontaneous: false
left: Phenylpyruvic acid
left: Oxygen
name: Oxygen + Phenylpyruvic acid → Carbon dioxide + ortho-Hydroxyphenylacetic acid
conversion direction: LEFT_TO_RIGHT

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

Reference/CAS 5801-57-0
type: UnificationXref
id: 5801-57-0
db: CAS

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

Reference/CAS 63-91-2
type: UnificationXref
id: 63-91-2
db: CAS

NADH
type: SmallMolecule
entity reference: NADH

Reference/KEGG Compound C05332
type: UnificationXref
id: C05332
db: KEGG Compound

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

Compound/PW C001065/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
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

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

Reaction180210
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001420/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000721/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000135/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001144/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002680/Stoichiometry/1.0
right: NADH
right: Hydrogen Ion
right: Phenylacetic acid
spontaneous: false
left: Water
left: Phenylacetaldehyde
left: NAD
name: NAD + Phenylacetaldehyde + Water ↔ Hydrogen Ion + NADH + Phenylacetic acid
conversion direction: REVERSIBLE

Reference/ChemSpider 50
type: UnificationXref
id: 50
db: ChemSpider

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

Reference/ChemSpider 5833
type: UnificationXref
id: 5833
db: ChemSpider

NAD
type: SmallMolecule
entity reference: NAD

Reference/UniProt Q7SZR0
type: UnificationXref
id: Q7SZR0
db: UniProt

Reference/PubChem-compound 1125
type: UnificationXref
id: 1125
db: PubChem-compound

4a-Carbinolamine tetrahydrobiopterin
type: SmallMolecule
entity reference: 4a-Carbinolamine tetrahydrobiopterin

1.4.3.4
type: BiochemicalReaction
participant stoichiometry: Compound/PW C007816/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001783/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002680/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000035/Stoichiometry/1.0
right: Hydrogen peroxide
right: Ammonia
right: Phenylacetaldehyde
spontaneous: false
EC number: 1.4.3.4
left: Water
left: Oxygen
left: Phenylethylamine
name: Oxygen + Phenylethylamine + Water ↔ Ammonia + Hydrogen peroxide + Phenylacetaldehyde
conversion direction: REVERSIBLE

Reaction180208
type: BiochemicalReaction
participant stoichiometry: Compound/PW C007816/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000104/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001316/Stoichiometry/1.0
right: Carbon dioxide
right: Phenylethylamine
spontaneous: false
left: L-Phenylalanine
name: L-Phenylalanine → Carbon dioxide + Phenylethylamine
conversion direction: LEFT_TO_RIGHT

Reference/PubChem-compound 1001
type: UnificationXref
id: 1001
db: PubChem-compound

Reference/ChEBI CHEBI 28478
type: UnificationXref
id: CHEBI:28478
db: ChEBI

ChemicalStructure/PW C000103
type: ChemicalStructure
structure format: SMILES
structure data: N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

Reference/UniProt Q7ZWF5
type: UnificationXref
id: Q7ZWF5
db: UniProt

Reference/PubChem-compound 51
type: UnificationXref
id: 51
db: PubChem-compound

4a-Carbinolamine tetrahydrobiopterin
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0002215
xref: Reference/BioCyc CPD-16
xref: Reference/CAS 79647-29-3
xref: Reference/PubChem-compound 133246
xref: Reference/KEGG Compound C00268
xref: Reference/ChemSpider 117564
chemical formula: C9H13N5O3
molecular weight: 239.10184
structure: ChemicalStructure/PW C001499

Reference/KEGG Compound C07086
type: UnificationXref
id: C07086
db: KEGG Compound

Reference/ChEBI CHEBI 16815
type: UnificationXref
id: CHEBI:16815
db: ChEBI

ChemicalStructure/PW C007772
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)C(\O)=C\C1=CC=CC=C1

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

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

Tat protein
type: Protein
cellular location: Mitochondrion
entity reference: Tat protein

Reference/ChemSpider 13876539
type: UnificationXref
id: 13876539
db: ChemSpider

Reference/HMDB HMDB0000669
type: UnificationXref
id: HMDB0000669
db: HMDB

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

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

ReactionCatalysis170064
type: Catalysis
controller: 4-hydroxyphenylpyruvate dioxygenase
controlled: Reaction180211
control type: ACTIVATION

ReactionCatalysis170063
type: Catalysis
controller: Aldehyde dehydrogenase
controlled: Reaction180210
control type: ACTIVATION

ReactionCatalysis170065
type: Catalysis
controller: Macrophage migration inhibitory factor
controlled: Reaction180212
control type: ACTIVATION

Ammonia
type: SmallMolecule
entity reference: Ammonia

Reference/ChemSpider 274
type: UnificationXref
id: 274
db: ChemSpider

Phenylacetic acid
type: SmallMoleculeReference
xref: Reference/BioCyc PHENYLACETATE
xref: Reference/PubChem-compound 999
xref: Reference/ChEBI CHEBI 30745
xref: Reference/KEGG Compound C07086
xref: Reference/HMDB HMDB0000209
xref: Reference/CAS 103-82-2
xref: Reference/ChemSpider 10181341
chemical formula: C8H8O2
molecular weight: 136.05243
structure: ChemicalStructure/PW C000135

Oxoglutaric acid
type: SmallMoleculeReference
xref: Reference/CAS 328-50-7
xref: Reference/PubChem-compound 51
xref: Reference/BioCyc 2-KETOGLUTARATE
xref: Reference/HMDB HMDB0000208
xref: Reference/ChEBI CHEBI 30915
xref: Reference/KEGG Compound C00026
xref: Reference/ChemSpider 50
chemical formula: C5H6O5
molecular weight: 146.02153
structure: ChemicalStructure/PW C000134

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

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

ReactionCatalysis170060
type: Catalysis
controller: Ddc protein
controlled: Reaction180208
control type: ACTIVATION

Phenylpyruvic acid
type: SmallMoleculeReference
xref: Reference/CAS 156-06-9
xref: Reference/ChEBI CHEBI 30851
xref: Reference/ChemSpider 972
xref: Reference/BioCyc PHENYL-PYRUVATE
xref: Reference/PubChem-compound 997
xref: Reference/HMDB HMDB0000205
xref: Reference/KEGG Compound C00166
chemical formula: C9H8O3
molecular weight: 164.04735
structure: ChemicalStructure/PW C000131

ReactionCatalysis170062
type: Catalysis
controller: Amine oxidase
controlled: 1.4.3.4
control type: ACTIVATION

Reference/ChemSpider 11476
type: UnificationXref
id: 11476
db: ChemSpider

ReactionCatalysis170061
type: Catalysis
controller: Amine oxidase [flavin-containing]
controlled: 1.4.3.4
control type: ACTIVATION

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

Reference/TAXONOMY 7955
type: UnificationXref
id: 7955
db: TAXONOMY

L-Glutamic acid
type: SmallMolecule
cellular location: Mitochondrion
entity reference: L-Glutamic acid

Tetrahydrobiopterin
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00272
xref: Reference/HMDB HMDB0000027
xref: Reference/CAS 17528-72-2
xref: Reference/BioCyc TETRA-H-BIOPTERIN
xref: Reference/PubChem-compound 1125
xref: Reference/ChemSpider 1093
xref: Reference/ChEBI CHEBI 15372
chemical formula: C9H15N5O3
molecular weight: 241.1175
structure: ChemicalStructure/PW C000019

Compound/PW C000104/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Phenylalanine
stoichiometric coefficient: 1.0

Reference/SMPDB SMP0121168
type: UnificationXref
id: SMP0121168
db: SMPDB

Aspartate aminotransferase
type: Protein
cellular location: Mitochondrion
entity reference: Aspartate aminotransferase

Reference/KEGG Compound C02763
type: UnificationXref
id: C02763
db: KEGG Compound

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

Compound/PW C000104 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Phenylalanine
stoichiometric coefficient: 1.0

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

Phenylacetaldehyde
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00601
xref: Reference/ChEBI CHEBI 16424
xref: Reference/ChemSpider 13876539
xref: Reference/PubChem-compound 998
xref: Reference/HMDB HMDB0006236
xref: Reference/CAS 122-78-1
xref: Reference/BioCyc HYDRPHENYLAC-CPD
chemical formula: C8H8O
molecular weight: 120.05752
structure: ChemicalStructure/PW C002680

Phenylacetaldehyde
type: SmallMolecule
entity reference: Phenylacetaldehyde

Reference/HMDB HMDB0000205
type: UnificationXref
id: HMDB0000205
db: HMDB

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

Reference/UniProt F1QRA1
type: UnificationXref
id: F1QRA1
db: UniProt

Hydrogen Ion
type: SmallMolecule
entity reference: Hydrogen Ion

Reference/HMDB HMDB0000208
type: UnificationXref
id: HMDB0000208
db: HMDB

SubPathwayInteraction110236
type: Interaction
name: SubPathway110236Reaction
name: SubPathwayReaction
participant: L-Phenylalanine

Phenylethylamine
type: SmallMoleculeReference
xref: Reference/KEGG Compound C05332
xref: Reference/CAS 64-04-0
xref: Reference/BioCyc PHENYLETHYLAMINE
xref: Reference/ChemSpider 13856352
xref: Reference/HMDB HMDB0012275
xref: Reference/ChEBI CHEBI 18397
xref: Reference/PubChem-compound 1001
chemical formula: C8H11N
molecular weight: 121.08915
structure: ChemicalStructure/PW C007816

SubPathwayInteraction110235
type: Interaction
name: SubPathwayReaction
name: SubPathway110235Reaction
participant: L-Tyrosine

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

Reference/HMDB HMDB0000209
type: UnificationXref
id: HMDB0000209
db: HMDB

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

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

ChemicalStructure/PW C000131
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)C(=O)CC1=CC=CC=C1

ChemicalStructure/PW C000135
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CC1=CC=CC=C1

ChemicalStructure/PW C000134
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CCC(=O)C(O)=O

Oxygen
type: SmallMolecule
entity reference: Oxygen

Reference/CAS 124-38-9
type: UnificationXref
id: 124-38-9
db: CAS

Reference/ChEBI CHEBI 30915
type: UnificationXref
id: CHEBI:30915
db: ChEBI

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

ChemicalStructure/PW C000019
type: ChemicalStructure
structure format: SMILES
structure data: CC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2

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

Phenylalanine hydroxylase
type: Protein
entity reference: Phenylalanine hydroxylase

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

ortho-Hydroxyphenylacetic acid
type: SmallMolecule
entity reference: ortho-Hydroxyphenylacetic acid

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

Reference/PathWhiz PW122512
type: UnificationXref
id: PW122512
db: PathWhiz

Reference/BioCyc PHENYL-PYRUVATE
type: UnificationXref
id: PHENYL-PYRUVATE
db: BioCyc

Amine oxidase
type: Protein
entity reference: Amine oxidase

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

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

Reference/PubChem-compound 133246
type: UnificationXref
id: 133246
db: PubChem-compound

ChemicalStructure/PW C002680
type: ChemicalStructure
structure format: SMILES
structure data: O=CCC1=CC=CC=C1

Reference/ChemSpider 117564
type: UnificationXref
id: 117564
db: ChemSpider

Reference/ChemSpider 556910
type: UnificationXref
id: 556910
db: ChemSpider

1.4.3.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001420/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000104/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000131/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001783/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000035/Stoichiometry/1.0
right: Hydrogen peroxide
right: Ammonia
right: Phenylpyruvic acid
spontaneous: false
EC number: 1.4.3.-
left: Water
left: Oxygen
left: L-Phenylalanine
name: L-Phenylalanine + Oxygen + Water → Ammonia + Hydrogen peroxide + Phenylpyruvic acid
conversion direction: LEFT_TO_RIGHT

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: C21H28N7O14P2
molecular weight: 664.11694
structure: ChemicalStructure/PW C000721

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

Reference/KEGG Compound C00011
type: UnificationXref
id: C00011
db: KEGG Compound

ChemicalStructure/PW C001316
type: ChemicalStructure
structure format: SMILES
structure data: O=C=O

ChemicalStructure/PW C000104
type: ChemicalStructure
structure format: SMILES
structure data: N[C@@H](CC1=CC=CC=C1)C(O)=O

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

Reference/UniProt Q0ZBR7
type: UnificationXref
id: Q0ZBR7
db: UniProt

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

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

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

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

2.6.1.1
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000131 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000095 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000104 Mitochondrion/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000134 Mitochondrion/Stoichiometry/1.0
right: L-Glutamic acid
right: Phenylpyruvic acid
spontaneous: false
EC number: 2.6.1.1
left: Oxoglutaric acid
left: L-Phenylalanine
name: L-Phenylalanine + Oxoglutaric acid ↔ L-Glutamic acid + Phenylpyruvic acid
conversion direction: REVERSIBLE

Reference/UniProt Q6NSN2
type: UnificationXref
id: Q6NSN2
db: UniProt

Reference/UniProt Q7ZU10
type: UnificationXref
id: Q7ZU10
db: UniProt

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

Phenylalanine and Tyrosine Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway110236
pathway component: SubPathwayInteraction110236
xref: Reference/PathWhiz PW122456
xref: Reference/SMPDB SMP0121168
name: SubPathway

Reference/HMDB HMDB0012225
type: UnificationXref
id: HMDB0012225
db: HMDB

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 C00268
type: UnificationXref
id: C00268
db: KEGG Compound

Reference/ChemSpider 13856352
type: UnificationXref
id: 13856352
db: ChemSpider

Phenylethylamine
type: SmallMolecule
entity reference: Phenylethylamine

Reference/KEGG Compound C00026
type: UnificationXref
id: C00026
db: KEGG Compound

Reference/KEGG Compound C00025
type: UnificationXref
id: C00025
db: KEGG Compound

Reference/CAS 614-75-5
type: UnificationXref
id: 614-75-5
db: CAS

Amine oxidase [flavin-containing]
type: ProteinReference
xref: Reference/UniProt Q6NSN2
organism: Danio rerio

Aldehyde dehydrogenase
type: ProteinReference
xref: Reference/UniProt Q7ZU10
organism: Danio rerio

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

Reference/KEGG Compound C00272
type: UnificationXref
id: C00272
db: KEGG Compound

Compound/PW C001499/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4a-Carbinolamine tetrahydrobiopterin
stoichiometric coefficient: 1.0

Compound/PW C000103/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Tyrosine
stoichiometric coefficient: 1.0

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

Amine oxidase
type: ProteinReference
xref: Reference/UniProt F1QRA1
organism: Danio rerio

Aspartate aminotransferase
type: ProteinReference
xref: Reference/UniProt Q7ZWF5
organism: Danio rerio

Tat protein
type: ProteinReference
xref: Reference/UniProt A0JMN6
organism: Danio rerio

Phenylalanine hydroxylase
type: ProteinReference
xref: Reference/UniProt Q6PHI7
organism: Danio rerio

ChemicalStructure/PW C000721
type: ChemicalStructure
structure format: SMILES

Macrophage migration inhibitory factor
type: Protein
entity reference: Macrophage migration inhibitory factor

Reference/ChEBI CHEBI 18397
type: UnificationXref
id: CHEBI:18397
db: ChEBI

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

ChemicalStructure/PW C001144
type: ChemicalStructure
structure format: SMILES

Reference/CAS 328-50-7
type: UnificationXref
id: 328-50-7
db: CAS

Reference/BioCyc CPD-16
type: UnificationXref
id: CPD-16
db: BioCyc

Water
type: SmallMolecule
entity reference: Water

Hydrogen peroxide
type: SmallMolecule
entity reference: Hydrogen peroxide

4-hydroxyphenylpyruvate dioxygenase
type: Protein
entity reference: 4-hydroxyphenylpyruvate dioxygenase

Tyrosine metabolism
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway110235
pathway component: SubPathwayInteraction110235
name: SubPathway

Amine oxidase
type: Protein
entity reference: Amine oxidase

Reference/BioCyc TETRA-H-BIOPTERIN
type: UnificationXref
id: TETRA-H-BIOPTERIN
db: BioCyc

Ddc protein
type: Protein
entity reference: Ddc protein

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

Reference/HMDB HMDB0006236
type: UnificationXref
id: HMDB0006236
db: HMDB

Reference/ChemSpider 10181341
type: UnificationXref
id: 10181341
db: ChemSpider

Reference/KEGG Compound C00601
type: UnificationXref
id: C00601
db: KEGG Compound

Reference/ChEBI CHEBI 16424
type: UnificationXref
id: CHEBI:16424
db: ChEBI

Reaction179730
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001420/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000019/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000104/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001499/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000103/Stoichiometry/1.0
right: Water
right: L-Tyrosine
right: 4a-Carbinolamine tetrahydrobiopterin
spontaneous: false
left: Oxygen
left: L-Phenylalanine
left: Tetrahydrobiopterin
name: L-Phenylalanine + Oxygen + Tetrahydrobiopterin → 4a-Carbinolamine tetrahydrobiopterin + L-Tyrosine + Water
conversion direction: LEFT_TO_RIGHT

Reference/PubChem-compound 999
type: UnificationXref
id: 999
db: PubChem-compound

Reference/UniProt F1R2V0
type: UnificationXref
id: F1R2V0
db: UniProt

Reference/PubChem-compound 997
type: UnificationXref
id: 997
db: PubChem-compound

Reference/PubChem-compound 998
type: UnificationXref
id: 998
db: PubChem-compound

Reference/KEGG Compound C00166
type: UnificationXref
id: C00166
db: KEGG Compound

Compound/PW C000134 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxoglutaric acid
stoichiometric coefficient: 1.0

Reference/KEGG Compound C05852
type: UnificationXref
id: C05852
db: KEGG Compound

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

Reference/HMDB HMDB0000027
type: UnificationXref
id: HMDB0000027
db: HMDB

Reference/HMDB HMDB0000148
type: UnificationXref
id: HMDB0000148
db: HMDB

Danio rerio
type: BioSource
xref: Reference/TAXONOMY 7955

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

ortho-Hydroxyphenylacetic acid
type: SmallMoleculeReference
xref: Reference/PubChem-compound 11970
xref: Reference/ChEBI CHEBI 28478
xref: Reference/HMDB HMDB0000669
xref: Reference/CAS 614-75-5
xref: Reference/ChemSpider 11476
xref: Reference/KEGG Compound C05852
chemical formula: C8H8O3
molecular weight: 152.04735
structure: ChemicalStructure/PW C000526

Reference/BioCyc ENOL-PHENYLPYRUVATE
type: UnificationXref
id: ENOL-PHENYLPYRUVATE
db: BioCyc

Oxoglutaric acid
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Oxoglutaric acid

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

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

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

Reference/HMDB HMDB0002215
type: UnificationXref
id: HMDB0002215
db: HMDB

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/HMDB HMDB0000158
type: UnificationXref
id: HMDB0000158
db: HMDB

Compound/PW C001316/Stoichiometry/1.0
type: Stoichiometry
physical entity: Carbon dioxide
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0000159
type: UnificationXref
id: HMDB0000159
db: HMDB

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

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

Reference/CAS 56-86-0
type: UnificationXref
id: 56-86-0
db: CAS

Reference/SMPDB SMP0121218
type: UnificationXref
id: SMP0121218
db: SMPDB

L-Glutamic acid
type: SmallMoleculeReference
xref: Reference/PubChem-compound 33032
xref: Reference/ChEBI CHEBI 16015
xref: Reference/ChemSpider 30572
xref: Reference/HMDB HMDB0000148
xref: Reference/CAS 56-86-0
xref: Reference/BioCyc GLT
xref: Reference/KEGG Compound C00025
chemical formula: C5H9NO4
molecular weight: 147.05316
structure: ChemicalStructure/PW C000095

Reference/CAS 156-06-9
type: UnificationXref
id: 156-06-9
db: CAS

Reference/PubChem-compound 33032
type: UnificationXref
id: 33032
db: PubChem-compound

Reference/CAS 60-18-4
type: UnificationXref
id: 60-18-4
db: CAS

Compound/PW C000019/Stoichiometry/1.0
type: Stoichiometry
physical entity: Tetrahydrobiopterin
stoichiometric coefficient: 1.0

Reference/CAS 64-04-0
type: UnificationXref
id: 64-04-0
db: CAS

Reference/ChEBI CHEBI 16526
type: UnificationXref
id: CHEBI:16526
db: ChEBI

Reference/ChEBI CHEBI 17295
type: UnificationXref
id: CHEBI:17295
db: ChEBI

Reference/ChemSpider 1093
type: UnificationXref
id: 1093
db: ChemSpider

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

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

Compound/PW C002680/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phenylacetaldehyde
stoichiometric coefficient: 1.0

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

Reference/CAS 79647-29-3
type: UnificationXref
id: 79647-29-3
db: CAS

Reference/UniProt A0JMN6
type: UnificationXref
id: A0JMN6
db: UniProt

ChemicalStructure/PW C001499
type: ChemicalStructure
structure format: SMILES

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

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

Reference/CAS 17528-72-2
type: UnificationXref
id: 17528-72-2
db: CAS

L-Phenylalanine
type: SmallMoleculeReference
xref: Reference/PubChem-compound 6140
xref: Reference/HMDB HMDB0000159
xref: Reference/ChemSpider 5910
xref: Reference/ChEBI CHEBI 17295
xref: Reference/BioCyc PHE
xref: Reference/CAS 63-91-2
xref: Reference/KEGG Compound C00079
chemical formula: C9H11NO2
molecular weight: 165.07898
structure: ChemicalStructure/PW C000104

Reference/BioCyc 2-KETOGLUTARATE
type: UnificationXref
id: 2-KETOGLUTARATE
db: BioCyc

Phenylalanine Metabolism
type: Pathway
pathway order: PathwayEnzymeReaction/2125353
pathway order: PathwayEnzymeReaction/2125355
pathway order: PathwayEnzymeReaction/2125354
pathway order: PathwayEnzymeReaction/2125346
pathway order: PathwayEnzymeReaction/2125357
pathway order: PathwayEnzymeReaction/2125347
pathway order: PathwayEnzymeReaction/2125358
pathway order: PathwayEnzymeReaction/2125360
pathway order: PathwaySubPathway/110236
pathway order: PathwayEnzymeReaction/2125351
pathway order: PathwaySubPathway/110235
pathway order: PathwayEnzymeReaction/2125350
pathway component: ReactionCatalysis169608
pathway component: ReactionCatalysis169607
pathway component: Phenylalanine and Tyrosine Biosynthesis
pathway component: ReactionCatalysis169606
pathway component: Reaction179730
pathway component: 1.4.3.-
pathway component: Reaction180212
pathway component: Reaction180211
pathway component: ReactionCatalysis169612
pathway component: 1.4.3.4
pathway component: Reaction180208
pathway component: ReactionCatalysis170064
pathway component: ReactionCatalysis170063
pathway component: ReactionCatalysis170065
pathway component: Tyrosine metabolism
pathway component: Reaction180210
pathway component: 2.6.1.1
pathway component: ReactionCatalysis170060
pathway component: ReactionCatalysis170062
pathway component: ReactionCatalysis170061
xref: Reference/PathWhiz PW122512
xref: Reference/SMPDB SMP0121218
organism: Danio rerio

L-Tyrosine
type: SmallMoleculeReference
xref: Reference/CAS 60-18-4
xref: Reference/PubChem-compound 6057
xref: Reference/HMDB HMDB0000158
xref: Reference/ChEBI CHEBI 17895
xref: Reference/KEGG Compound C00082
xref: Reference/ChemSpider 5833
xref: Reference/BioCyc TYR
chemical formula: C9H11NO3
molecular weight: 181.0739
structure: ChemicalStructure/PW C000103

Compound/PW C007772/Stoichiometry/1.0
type: Stoichiometry
physical entity: Enol-phenylpyruvate
stoichiometric coefficient: 1.0

Carbon dioxide
type: SmallMoleculeReference
xref: Reference/PubChem-compound 280
xref: Reference/ChEBI CHEBI 16526
xref: Reference/ChemSpider 274
xref: Reference/HMDB HMDB0001967
xref: Reference/CAS 124-38-9
xref: Reference/KEGG Compound C00011
chemical formula: CO2
molecular weight: 43.98983
structure: ChemicalStructure/PW C001316

Phenylacetic acid
type: SmallMolecule
entity reference: Phenylacetic acid

Tetrahydrobiopterin
type: SmallMolecule
entity reference: Tetrahydrobiopterin

Reference/HMDB HMDB0012275
type: UnificationXref
id: HMDB0012275
db: HMDB

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

Reference/KEGG Compound C00079
type: UnificationXref
id: C00079
db: KEGG Compound

ChemicalStructure/PW C000526
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CC1=C(O)C=CC=C1

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

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

Reference/ChemSpider 972
type: UnificationXref
id: 972
db: ChemSpider

Compound/PW C000131 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phenylpyruvic acid
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00082
type: UnificationXref
id: C00082
db: KEGG Compound

Phenylpyruvic acid
type: SmallMolecule
entity reference: Phenylpyruvic acid

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

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

ChemicalStructure/PW C000095
type: ChemicalStructure
structure format: SMILES
structure data: N[C@@H](CCC(O)=O)C(O)=O

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

Reference/PubChem-compound 6057
type: UnificationXref
id: 6057
db: PubChem-compound

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+]

4-hydroxyphenylpyruvate dioxygenase
type: ProteinReference
xref: Reference/UniProt Q7ZUY6
organism: Danio rerio

Macrophage migration inhibitory factor
type: ProteinReference
xref: Reference/UniProt Q0ZBR7
organism: Danio rerio

Reference/ChemSpider 5910
type: UnificationXref
id: 5910
db: ChemSpider

Ddc protein
type: ProteinReference
xref: Reference/UniProt Q7SZR0
organism: Danio rerio

Amine oxidase
type: ProteinReference
xref: Reference/UniProt F1R2V0
organism: Danio rerio

Compound/PW C000526/Stoichiometry/1.0
type: Stoichiometry
physical entity: ortho-Hydroxyphenylacetic acid
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 15372
type: UnificationXref
id: CHEBI:15372
db: ChEBI

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

Reference/PubChem-compound 280
type: UnificationXref
id: 280
db: PubChem-compound

Reference/ChEBI CHEBI 30745
type: UnificationXref
id: CHEBI:30745
db: ChEBI

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

Reference/CAS 122-78-1
type: UnificationXref
id: 122-78-1
db: CAS

Reference/CAS 103-82-2
type: UnificationXref
id: 103-82-2
db: CAS

ChemicalStructure/PW C007816
type: ChemicalStructure
structure format: SMILES
structure data: NCCC1=CC=CC=C1

Reference/ChEBI CHEBI 30851
type: UnificationXref
id: CHEBI:30851
db: ChEBI

Compound/PW C000131/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phenylpyruvic acid
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

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

Compound/PW C000135/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phenylacetic acid
stoichiometric coefficient: 1.0

Compound/PW C000095 Mitochondrion/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Glutamic acid
stoichiometric coefficient: 1.0

Reference/PubChem-compound 641637
type: UnificationXref
id: 641637
db: PubChem-compound

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

Aldehyde dehydrogenase
type: Protein
entity reference: Aldehyde dehydrogenase

Amine oxidase [flavin-containing]
type: Protein
entity reference: Amine oxidase [flavin-containing]

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

Reference/ChEBI CHEBI 17895
type: UnificationXref
id: CHEBI:17895
db: ChEBI

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

L-Phenylalanine
type: SmallMolecule
cellular location: Mitochondrion
entity reference: L-Phenylalanine

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

ReactionCatalysis169612
type: Catalysis
controller: Phenylalanine hydroxylase
controlled: Reaction179730
control type: ACTIVATION

Carbon dioxide
type: SmallMolecule
entity reference: Carbon dioxide

L-Phenylalanine
type: SmallMolecule
entity reference: L-Phenylalanine
name: SubPathwayOutput

Reference/HMDB HMDB0001967
type: UnificationXref
id: HMDB0001967
db: HMDB

L-Tyrosine
type: SmallMolecule
entity reference: L-Tyrosine
name: SubPathwayInput

Reference/PathWhiz PW122456
type: UnificationXref
id: PW122456
db: PathWhiz

Compound/PW C007816/Stoichiometry/1.0
type: Stoichiometry
physical entity: Phenylethylamine
stoichiometric coefficient: 1.0

Phenylpyruvic acid
type: SmallMolecule
cellular location: Mitochondrion
entity reference: Phenylpyruvic acid

Enol-phenylpyruvate
type: SmallMolecule
entity reference: Enol-phenylpyruvate

Reference/UniProt Q6PHI7
type: UnificationXref
id: Q6PHI7
db: UniProt

Enol-phenylpyruvate
type: SmallMoleculeReference
xref: Reference/ChemSpider 556910
xref: Reference/BioCyc ENOL-PHENYLPYRUVATE
xref: Reference/HMDB HMDB0012225
xref: Reference/KEGG Compound C02763
xref: Reference/PubChem-compound 641637
xref: Reference/ChEBI CHEBI 16815
xref: Reference/CAS 5801-57-0
chemical formula: C9H8O3
molecular weight: 164.04735
structure: ChemicalStructure/PW C007772

Reference/UniProt Q7ZUY6
type: UnificationXref
id: Q7ZUY6
db: UniProt