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Tryptophan metabolism

State Icon Reaction EC-Number Confidence maximal confidence score from EnzymeDetector
2 3-Hydroxyanthranilate + 4 O2 <=> Cinnabarinic_acid + 2 O2- + 2 H2O2 + 2 H+ 1.11.1.21 catalase-peroxidase
1.11.1.6 catalase


L-tryptophan + O2 <=> N-formyl-L-kynurenine 1.13.11.11 tryptophan 2,3-dioxygenase
1.13.11.26 peptide-tryptophan 2,3-dioxygenase
1.13.11.52 indoleamine 2,3-dioxygenase



acetyl-CoA + serotonin <=> H+ + CoA + N-acetylserotonin 2.3.1.5 arylamine N-acetyltransferase
2.3.1.87 aralkylamine N-acetyltransferase


4-(2-Amino-5-hydroxyphenyl)-2,4-dioxobutanoate <=> 6-Hydroxykynurenate + H2O not assigned

5-hydroxy-L-tryptophan + O2 <=> 5-hydroxy-N-formylkynurenine 1.13.11.26 peptide-tryptophan 2,3-dioxygenase
1.13.11.52 indoleamine 2,3-dioxygenase


indole-3-acetic_acid + 2-oxoglutarate + O2 <=> 2-oxoindole-3-acetate + succinate + CO2 1.14.11

2-aminomuconate + H2O <=> 2-hydroxy-2,4-hexadienedioate + NH3 3.5.99.11 2-aminomuconate deaminase (2-hydroxymuconate-forming)
3.5.99.5 2-aminomuconate deaminase


L-tryptophan + H2O + O2 <=> 3-Indole-2-oxopropanoate + NH3 + H2O2 1.4.3.2 L-amino-acid oxidase

alpha-amino-beta-carboxymuconate-epsilon-semialdehyde <=> quinolinic_acid + H2O + H+ not assigned

S-(Indolylmethylthiohydroximoyl)-L-cysteine + H2O <=> 2-(3-indolyl)acetothiohydroximate + pyruvate + NH3 4.4.1

Melatonin + O2 <=> Formyl-N-acetyl-5-methoxykynurenamine 1.13.11.52 indoleamine 2,3-dioxygenase

5-Hydroxykynurenamine + CO2 <=> 5-hydroxy-L-kynurenine 4.1.1.28 aromatic-L-amino-acid decarboxylase

N-Hydroxyl-tryptamine <=> (E,Z)-indolyl-3-acetaldoxime 2.5.1

5-hydroxyindoleacetate <=> 5-Hydroxyindoleacetylglycine 6.3.2

H+ + L-tryptophan <=> CO2 + tryptamine 4.1.1.105 L-tryptophan decarboxylase
4.1.1.28 aromatic-L-amino-acid decarboxylase
4.1.1.53 phenylalanine decarboxylase



O2 + N-Acetylindoxyl <=> H2O + N-Acetylisatin 1.7.3.2 acetylindoxyl oxidase

Indole-3-acetamide <=> indole-3-acetonitrile + H2O 4.2.1.84 nitrile hydratase

2-oxoadipate + NAD+ + CoA <=> CO2 + NADH + glutaryl-CoA 1.2.1.ak
1.2.4.2 oxoglutarate dehydrogenase (succinyl-transferring)
1.8.1.4 dihydrolipoyl dehydrogenase
2.3.1.61 dihydrolipoyllysine-residue succinyltransferase




S-adenosyl-L-methionine + serotonin <=> S-adenosyl-L-homocysteine + N-methylserotonin 2.1.1.49 amine N-methyltransferase

(R)-(indol-3-yl)lactate + NAD+ <=> 3-Indole-2-oxopropanoate + NADH + H+ 1.1.1.110 aromatic 2-oxoacid reductase

indole-3-acetic_acid + O2 <=> 3-Methyldioxyindole + CO2 not assigned

S-adenosyl-L-methionine + tryptamine <=> S-adenosyl-L-homocysteine + N-methyltryptamine + H+ 2.1.1.49 amine N-methyltransferase

Melatonin + reduced_flavodoxin + O2 <=> 6-hydroxymelatonin + flavin + H2O 1.14.14.1 unspecific monooxygenase

N-formyl-L-kynurenine + H2O <=> N-formylanthranilic_acid + L-alanine 3.7.1.3 kynureninase

UDP-glucose + 2-(3-indolyl)acetothiohydroximate <=> desulfo-indol-3-yl-methyl_glucosinolate + UDP 2.4.1.195 N-hydroxythioamide S-beta-glucosyltransferase

serotonin + 5-methyltetrahydrofolate <=> 5-methoxytryptamine + tetrahydrofolate 2.1.1

Indole-3-acetaldehyde + O2 + H2O <=> H+ + indole-3-acetic_acid + H2O2 1.2.3.1 aldehyde oxidase
1.2.3.7 indole-3-acetaldehyde oxidase


2-Aminophenol + O2 <=> Isophenoxazine + H2O 1.10.3.4 o-aminophenol oxidase

glutaryl-CoA + flavin <=> crotonyl-CoA + CO2 + reduced_flavodoxin 1.3.8.6 glutaryl-CoA dehydrogenase (ETF)

indole-3-acetic_acid + H+ <=> 3-Methylindole + CO2 4.1.1.115 indoleacetate decarboxylase

serotonin + O2 <=> Formyl-5-hydroxykynurenamine 1.13.11.52 indoleamine 2,3-dioxygenase

2-oxoadipate + NH3 + NADP+ <=> 2-aminomuconate + NADPH + H+ + H2O 1.5.1

(E,Z)-indolyl-3-acetaldoxime <=> indole-3-acetonitrile + H2O 4.99.1.6 indoleacetaldoxime dehydratase
4.99.1.7 phenylacetaldoxime dehydratase


N-formylanthranilic_acid + H2O <=> formate + anthranilate 3.5.1.9 arylformamidase

Kynurenic_acid + NADH + O2 <=> 7,8-Dihydro-7,8-dihydroxykynurenate + NAD+ 1.14.99.2 kynurenine 7,8-hydroxylase

5-(2''-Formylethyl)-4,6-dihydroxypicolinate + CO2 <=> 5-(3''-Carboxy-3''-oxopropyl)-4,6-dihydroxypicolinate not assigned

5-hydroxyindoleacetate + S-adenosyl-L-methionine <=> S-adenosyl-L-homocysteine + 5-methoxyindoleacetic_acid 2.1.1.4 acetylserotonin O-methyltransferase

L-tryptophan + 4-methylsulfanyl-2-oxobutanoate <=> 3-Indole-2-oxopropanoate + L-methionine 2.6.1
2.6.1.27 tryptophan transaminase
2.6.1.57 aromatic-amino-acid transaminase
2.6.1.88 methionine transaminase
2.6.1.99 L-tryptophan---pyruvate aminotransferase





Indole-3-acetaldehyde + NAD+ + H2O <=> indole-3-acetic_acid + NADH + H+ 1.17.1.4 xanthine dehydrogenase
1.2.1.3 aldehyde dehydrogenase (NAD+)
1.2.1.39 phenylacetaldehyde dehydrogenase
1.2.1.5 aldehyde dehydrogenase [NAD(P)+]
1.2.1.88 L-glutamate gamma-semialdehyde dehydrogenase





2-aminomuconate_6-semialdehyde + NAD+ + H2O <=> 2-aminomuconate + NADH + H+ 1.2.1.32 aminomuconate-semialdehyde dehydrogenase

(5-hydroxy-1H-indol-3-yl)acetaldehyde + NAD+ + H2O <=> 5-hydroxyindoleacetate + NADH + H+ 1.2.1.3 aldehyde dehydrogenase (NAD+)
1.2.1.5 aldehyde dehydrogenase [NAD(P)+]


(E,Z)-indolyl-3-acetaldoxime + L-cysteine + NADPH + O2 + H+ <=> S-(Indolylmethylthiohydroximoyl)-L-cysteine + NADP+ + 2 H2O 1.14.14.43 (methylsulfanyl)alkanaldoxime N-monooxygenase
1.14.14.45 aromatic aldoxime N-monooxygenase


indole-3-acetic_acid + O2 <=> 2-Formaminobenzoylacetate 1.13.11

L-tryptophan + 2-oxoglutarate <=> 3-Indole-2-oxopropanoate + L-glutamate 2.6.1.1 aspartate transaminase
2.6.1.24 diiodotyrosine transaminase
2.6.1.26 thyroid-hormone transaminase
2.6.1.27 tryptophan transaminase
2.6.1.28 tryptophan---phenylpyruvate transaminase
2.6.1.39 2-aminoadipate transaminase
2.6.1.42 branched-chain-amino-acid transaminase
2.6.1.5 tyrosine transaminase
2.6.1.57 aromatic-amino-acid transaminase
2.6.1.7 kynurenine---oxoglutarate transaminase
2.6.1.9 histidinol-phosphate transaminase











alpha-amino-beta-carboxymuconate-epsilon-semialdehyde + H+ <=> 2-aminomuconate_6-semialdehyde + CO2 4.1.1.45 aminocarboxymuconate-semialdehyde decarboxylase

(S)-3-hydroxybutyryl-CoA + NAD+ <=> acetoacetyl-CoA + NADH + H+ 1.1.1.178 3-hydroxy-2-methylbutyryl-CoA dehydrogenase
1.1.1.35 3-hydroxyacyl-CoA dehydrogenase
1.1.1.36 acetoacetyl-CoA reductase



3''-phosphoadenylyl-sulfate + desulfo-indol-3-yl-methyl_glucosinolate <=> adenosine_3,5''-bisphosphate + glucobrassicin + H+ 2.8.2.24 aromatic desulfoglucosinolate sulfotransferase
2.8.2.38 aliphatic desulfoglucosinolate sulfotransferase


2-oxoadipate + NH3 + NAD+ <=> 2-aminomuconate + NADH + H+ + H2O 1.5.1

L-tryptophan + O2 <=> 3-Indoleglycolaldehyde + CO2 + NH3 1.13.99.3 tryptophan 2'-dioxygenase

tryptophol + NADP+ <=> H+ + NADPH + Indole-3-acetaldehyde 1.1.1
1.1.1.191 indole-3-acetaldehyde reductase (NADPH)
1.1.1.2 alcohol dehydrogenase (NADP+)
1.1.1.21 aldose reductase




indole-3-acetonitrile + H2O <=> indole-3-acetic_acid + NH3 3.5.5.1 nitrilase
3.5.5.5 arylacetonitrilase
3.5.5.7 aliphatic nitrilase



NAD+ + 7,8-Dihydro-7,8-dihydroxykynurenate <=> NADH + 7,8-Dihydroxykynurenate 1.3.1.18 kynurenate-7,8-dihydrodiol dehydrogenase

H+ + 3-Indole-2-oxopropanoate <=> CO2 + Indole-3-acetaldehyde 4.1.1.1 pyruvate decarboxylase
4.1.1.43 phenylpyruvate decarboxylase
4.1.1.72 branched-chain-2-oxoacid decarboxylase
4.1.1.74 indolepyruvate decarboxylase




N-Acetylindoxyl <=> 3-hydroxyindole not assigned

3-Hydroxyanthranilate + O2 <=> alpha-amino-beta-carboxymuconate-epsilon-semialdehyde 1.13.11.6 3-hydroxyanthranilate 3,4-dioxygenase

5-(3''-Carboxy-3''-oxopropenyl)-4,6-dihydroxypicolinate + NADPH + H+ <=> 5-(3''-Carboxy-3''-oxopropyl)-4,6-dihydroxypicolinate + NADP+ 1.3.1

L-tryptophan + 2 reduced_flavodoxin + 2 O2 <=> (E,Z)-indolyl-3-acetaldoxime + 2 flavin + CO2 + 3 H2O 1.14.14.156 tryptophan N-monooxygenase

(E,Z)-indolyl-3-acetaldoxime <=> Indole-3-acetaldehyde 1.7.3

tryptamine + H2O + O2 <=> NH3 + Indole-3-acetaldehyde + H2O2 1.4.3.10 putrescine oxidase
1.4.3.21 primary-amine oxidase
1.4.3.22 diamine oxidase
1.4.3.4 monoamine oxidase
1.4.3.5 pyridoxal 5'-phosphate synthase
1.5.3.17 non-specific polyamine oxidase






5-hydroxy-N-formylkynurenine + H2O <=> 5-hydroxy-L-kynurenine + formate 3.5.1.9 arylformamidase

2,3-Dihydroxyindole + O2 <=> H+ + anthranilate + CO2 1.13.11.23 2,3-dihydroxyindole 2,3-dioxygenase

5-(2''-Formylethyl)-4,6-dihydroxypicolinate + NADP+ + H2O <=> 5-(2''-Carboxyethyl)-4,6-dihydroxypicolinate + NADPH + H+ 1.2.1

5-(2''-Formylethyl)-4,6-dihydroxypicolinate + NAD+ + H2O <=> 5-(2''-Carboxyethyl)-4,6-dihydroxypicolinate + NADH + H+ 1.2.1

O2 + indole <=> 2-formylaminobenzaldehyde 1.13.11.17 indole 2,3-dioxygenase

tetrahydrobiopterin + L-tryptophan + O2 <=> 5-hydroxy-L-tryptophan + dihydrobiopterin + H2O 1.14.16.4 tryptophan 5-monooxygenase

acetyl-CoA <=> acetoacetyl-CoA + CoA 1.1.1.34 hydroxymethylglutaryl-CoA reductase (NADPH)
2.3.1.155 acetyl-CoA C-myristoyltransferase
2.3.1.16 acetyl-CoA C-acyltransferase
2.3.1.38 [acyl-carrier-protein] S-acetyltransferase
2.3.1.9 acetyl-CoA C-acetyltransferase





5-hydroxy-L-kynurenine + a_2-oxo_carboxylate <=> 4-(2-Amino-5-hydroxyphenyl)-2,4-dioxobutanoate + amino_acid 2.6.1

tryptamine + O2 + NADPH <=> N-Hydroxyl-tryptamine + H2O + NADP+ 1.14.13

L-tryptophan + H2O <=> indole + pyruvate + NH3 4.1.99.1 tryptophanase

3-Hydroxyanthranilate <=> 2-Aminophenol + CO2 4.1.1

2-aminomuconate_6-semialdehyde <=> Picolinic_acid + H2O + H+ not assigned

4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoate <=> H+ + xanthurenic_acid + H2O not assigned

anthranilate + O2 + FADH2 <=> H+ + 3-Hydroxyanthranilate + H2O + FAD 1.14.14.8 anthranilate 3-monooxygenase (FAD)

(5-hydroxy-1H-indol-3-yl)acetaldehyde + O2 + H2O <=> 5-hydroxyindoleacetate + H2O2 1.2.3.1 aldehyde oxidase

4-(2-aminophenyl)-2,4-dioxobutanoate <=> Kynurenic_acid + H2O + H+ 0.0.0.0

tryptophol + NAD+ <=> H+ + NADH + Indole-3-acetaldehyde 1.1.1
1.1.1.1 alcohol dehydrogenase
1.1.1.190 indole-3-acetaldehyde reductase (NADH)
1.1.1.21 aldose reductase




(S)-3-hydroxybutyryl-CoA <=> H2O + crotonyl-CoA 1.3.8.7 medium-chain acyl-CoA dehydrogenase
4.2.1.116 3-hydroxypropionyl-CoA dehydratase
4.2.1.150 short-chain-enoyl-CoA hydratase
4.2.1.17 enoyl-CoA hydratase




Kynurenic_acid + NADPH + O2 <=> 7,8-Dihydro-7,8-dihydroxykynurenate + NADP+ 1.14.99.2 kynurenine 7,8-hydroxylase

3-Indole-2-oxopropanoate + NADPH + O2 + H+ <=> indole-3-acetic_acid + CO2 + NADP+ + H2O 1.14.13.168 indole-3-pyruvate monooxygenase

S-adenosyl-L-methionine + N-acetylserotonin <=> H+ + S-adenosyl-L-homocysteine + Melatonin 2.1.1.4 acetylserotonin O-methyltransferase

5-Hydroxykynurenamine + H2O + O2 <=> 4,6-Dihydroxyquinoline + NH3 + H2O2 + H2O 1.4.3.4 monoamine oxidase

O2 + 7,8-Dihydroxykynurenate <=> 5-(3-Carboxy-3-oxopropenyl)-4,6-dihydroxypyridine-2-carboxylate + H+ 1.13.11.10 7,8-dihydroxykynurenate 8,8a-dioxygenase

O2 + L-tryptophan <=> Indole-3-acetamide + H2O + CO2 1.13.12.3 tryptophan 2-monooxygenase

5-hydroxy-L-tryptophan + 2-oxoglutarate <=> 3-(5-Hydroxyindole)-2-oxopropanoate + L-glutamate 2.6.1.27 tryptophan transaminase
2.6.1.57 aromatic-amino-acid transaminase


L-tryptophan + pyruvate <=> 3-Indole-2-oxopropanoate + L-alanine 2.6.1.28 tryptophan---phenylpyruvate transaminase
2.6.1.44 alanine---glyoxylate transaminase
2.6.1.5 tyrosine transaminase
2.6.1.51 serine---pyruvate transaminase
2.6.1.57 aromatic-amino-acid transaminase
2.6.1.64 glutamine---phenylpyruvate transaminase
2.6.1.99 L-tryptophan---pyruvate aminotransferase







L-kynurenine + H2O <=> H+ + L-alanine + anthranilate 3.7.1.3 kynureninase

L-3-hydroxykynurenine <=> 3-Hydroxykynurenamine + CO2 4.1.1

indole <=> indole-3-acetic_acid 2.5.1

L-kynurenine + 2-oxoglutarate <=> L-glutamate + 4-(2-aminophenyl)-2,4-dioxobutanoate 2.6.1.7 kynurenine---oxoglutarate transaminase
2.6.1.75 cysteine-conjugate transaminase


S-adenosyl-L-methionine + 3-Indole-2-oxopropanoate <=> S-adenosyl-L-homocysteine + 3-Methylindolepyruvate 2.1.1.47 indolepyruvate C-methyltransferase

xanthurenic_acid + S-adenosyl-L-methionine <=> 8-Methoxykynurenate + S-adenosyl-L-homocysteine 2.1.1

5-hydroxy-L-tryptophan + H+ <=> serotonin + CO2 4.1.1.28 aromatic-L-amino-acid decarboxylase
4.1.1.53 phenylalanine decarboxylase


L-3-hydroxykynurenine + H2O <=> H+ + 3-Hydroxyanthranilate + L-alanine 3.7.1.3 kynureninase

anthranilate <=> 2-Formaminobenzoylacetate not assigned

3-Hydroxykynurenamine + O2 <=> 4,8-Dihydroxyquinoline + NH3 + H2O2 1.4.3.4 monoamine oxidase

L-kynurenine + O2 + NADPH + H+ <=> L-3-hydroxykynurenine + H2O + NADP+ 1.14.13.9 kynurenine 3-monooxygenase

Indole-3-acetamide + H2O <=> indole-3-acetic_acid + NH3 3.5.1
3.5.1.4 amidase


3-Hydroxyanthranilate + S-adenosyl-L-methionine <=> 3-Methoxyanthranilate + S-adenosyl-L-homocysteine 2.1.1

indole + NADPH + H+ + O2 <=> 3-hydroxyindole + NADP+ + H2O 1.14.13.8 flavin-containing monooxygenase
1.14.16


L-3-hydroxykynurenine + 2-oxoglutarate <=> 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoate + L-glutamate 2.6.1.7 kynurenine---oxoglutarate transaminase

N-formyl-L-kynurenine + H2O <=> L-kynurenine + formate + H+ 3.5.1.9 arylformamidase

serotonin + O2 + H2O <=> (5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2 1.4.3.21 primary-amine oxidase
1.4.3.4 monoamine oxidase


glucobrassicin + H2O <=> indole-3-acetonitrile + D-glucose + sulfate + sulfur 3.2.1.147 thioglucosidase

Visualization of the pathway