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Phenylalanine metabolism

State Icon Reaction EC-Number Confidence maximal confidence score from EnzymeDetector
3-Phenylpropionic_acid + NADH + O2 + H+ <=> 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+ 1.14.12.19 3-phenylpropanoate dioxygenase

phenylpyruvate + O2 <=> 2-hydroxyphenylacetate + CO2 1.13.11.27 4-hydroxyphenylpyruvate dioxygenase

2-Phenylethylamine + O2 + H2O <=> phenylacetaldehyde + NH3 + H2O2 1.4.3.21 primary-amine oxidase
1.4.3.22 diamine oxidase
1.4.3.4 monoamine oxidase
1.5.3.5 (S)-6-hydroxynicotine oxidase




3-hydroxycinnamic_acid + O2 + NADH + H+ <=> (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + H2O + NAD+ 1.14.13.127 3-(3-hydroxyphenyl)propanoate hydroxylase

acetaldehyde + CoA + NAD+ <=> acetyl-CoA + NADH + H+ 1.2.1.10 acetaldehyde dehydrogenase (acetylating)
1.2.1.42 hexadecanal dehydrogenase (acylating)
1.2.1.57 butanal dehydrogenase
1.2.1.87 propanal dehydrogenase (CoA-propanoylating)




2,3-dehydroadipyl-CoA + acetyl-CoA <=> 3-oxo-5,6-dehydrosuberyl-CoA + CoA 2.3.1.16 acetyl-CoA C-acyltransferase
2.3.1.223 3-oxo-5,6-didehydrosuberyl-CoA thiolase


phenylacetate <=> 3-hydroxyphenylacetate not assigned

melilotate <=> 3-Phenylpropionic_acid not assigned

H+ + L-phenylalanine + O2 + H2O <=> phenylacetaldehyde + NH3 + H2O2 + CO2 4.1.1.109 phenylacetaldehyde synthase

L-phenylalanine + O2 <=> phenylacetamide + CO2 + H2O 1.11.1.21 catalase-peroxidase
1.13.12.3 tryptophan 2-monooxygenase
1.13.12.9 phenylalanine 2-monooxygenase



benzoylformate + CoA + NAD+ <=> benzoyl-CoA + CO2 + NADH 1.2.1.58 phenylglyoxylate dehydrogenase (acylating)
1.2.4.1 pyruvate dehydrogenase (acetyl-transferring)


(1R,2S)-ephedrine + NAD+ <=> (R)-2-Methylimino-1-phenylpropan-1-ol + NADH + H+ 1.5.1.18 ephedrine dehydrogenase

acetyl-CoA + D-Phe <=> CoA + N-Acetyl-D-Phe 2.3.1.36 D-amino-acid N-acetyltransferase

melilotate + NAD+ <=> H+ + NADH + coumaric_acid 1.3.1.11 2-coumarate reductase
1.3.1.31 2-enoate reductase


benzoate + pyruvate <=> 1-phenyl-1,2-propanedione + CO2 not assigned

3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+ <=> H+ + 3-(2,3-dihydroxyphenyl)propanoate + NADH 1.3.1.87 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate dehydrogenase

3-(2,3-dihydroxyphenyl)propanoate + O2 <=> H+ + (2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate 1.13.11.16 3-carboxyethylcatechol 2,3-dioxygenase

L-phenylalanine <=> Cinnamic_acid + NH3 4.3.1.1 aspartate ammonia-lyase
4.3.1.23 tyrosine ammonia-lyase
4.3.1.24 phenylalanine ammonia-lyase
4.3.1.25 phenylalanine/tyrosine ammonia-lyase
4.3.1.31 L-tryptophan ammonia lyase
4.3.1.5 phenylalanine ammonia-lyase






phenylacetamide + H2O <=> phenylacetate + NH3 3.5.1.11 penicillin amidase
3.5.1.4 amidase
3.5.1.86 mandelamide amidase



S-adenosyl-L-methionine + D-Cathine <=> (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + S-adenosyl-L-homocysteine + H+ 2.1.1
2.1.1.M76


(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O <=> 2-hydroxy-2,4-pentadienoate + succinate 3.7.1.14 2-hydroxy-6-oxonona-2,4-dienedioate hydrolase

L-phenylalanine + NAD+ + H2O <=> phenylpyruvate + NH3 + NADH + H+ 1.4.1.1 alanine dehydrogenase
1.4.1.19 tryptophan dehydrogenase
1.4.1.20 phenylalanine dehydrogenase
1.4.1.5 L-amino-acid dehydrogenase
1.4.1.8 valine dehydrogenase (NADP+)
1.4.1.9 leucine dehydrogenase






2-phenylethanol + NAD+ <=> H+ + phenylacetaldehyde + NADH 1.1.1.1 alcohol dehydrogenase
1.1.1.190 indole-3-acetaldehyde reductase (NADH)
1.1.1.71 alcohol dehydrogenase [NAD(P)+]
1.1.1.90 aryl-alcohol dehydrogenase
1.1.1.B3





4-hydroxy-2-oxopentanoate <=> pyruvate + acetaldehyde 4.1.2.52 4-hydroxy-2-oxoheptanedioate aldolase
4.1.3.17 4-hydroxy-4-methyl-2-oxoglutarate aldolase
4.1.3.39 4-hydroxy-2-oxovalerate aldolase
4.1.3.43 4-hydroxy-2-oxohexanoate aldolase




succinyl-CoA + acetyl-CoA <=> 3-oxoadipyl-CoA + CoA 2.3.1.16 acetyl-CoA C-acyltransferase
2.3.1.174 3-oxoadipyl-CoA thiolase


phenylacetaldehyde + NADP+ + H2O <=> phenylacetate + NADPH + H+ 1.2.1.19 aminobutyraldehyde dehydrogenase
1.2.1.39 phenylacetaldehyde dehydrogenase
1.2.1.5 aldehyde dehydrogenase [NAD(P)+]
1.2.1.8 betaine-aldehyde dehydrogenase




H+ + melilotate + O2 + NADH <=> 3-(2,3-dihydroxyphenyl)propanoate + H2O + NAD+ 1.14.13.4 melilotate 3-monooxygenase

trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylic_acid + NAD+ <=> (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NADH + H+ 1.3.1.87 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate dehydrogenase

(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + O2 <=> (2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H+ 1.13.11.16 3-carboxyethylcatechol 2,3-dioxygenase

(3S)-3-hydroxyadipyl-CoA <=> 2,3-dehydroadipyl-CoA + H2O 4.2.1.17 enoyl-CoA hydratase

S-adenosyl-L-methionine + (-)-Norephedrine <=> (1R,2S)-ephedrine + H+ + S-adenosyl-L-homocysteine 2.1.1
2.1.1.M76


L-phenylalanine + acetyl-CoA <=> H+ + N-acetyl-L-phenylalanine + CoA 2.3.1.53 phenylalanine N-acetyltransferase

phenylpyruvate + NADPH <=> D-phenyllactate + NADP+ 1.1.1.110 aromatic 2-oxoacid reductase
1.1.1.237 hydroxyphenylpyruvate reductase
1.1.1.28 D-lactate dehydrogenase
1.1.1.79 glyoxylate reductase (NADP+)




phenylacetyl-CoA + glycine <=> H+ + N-benzoyl-Gly + CoA 2.3.1.13 glycine N-acyltransferase
2.3.1.192 glycine N-phenylacetyltransferase
2.3.1.71 glycine N-benzoyltransferase



3-Phenylpropionic_acid <=> 3-(3-Hydroxyphenyl)propanoic_acid not assigned

H2O + L-phenylalanine + ATP <=> H+ + D-Phe + diphosphate + AMP 5.1.1.11 phenylalanine racemase (ATP-hydrolysing)

L-glutamine + phenylacetyl-CoA <=> H+ + alpha-N-phenylacetyl-L-glutamine + CoA 2.3.1.14 glutamine N-phenylacetyltransferase
2.3.1.192 glycine N-phenylacetyltransferase
2.3.1.68 glutamine N-acyltransferase
2.3.1.71 glycine N-benzoyltransferase




phenylacetate <=> 4-hydroxyphenylacetate not assigned

phenylacetate + ATP + CoA <=> phenylacetyl-CoA + AMP + diphosphate 6.2.1.2 medium-chain acyl-CoA ligase
6.2.1.27 4-hydroxybenzoate---CoA ligase
6.2.1.30 phenylacetate---CoA ligase



benzoate + NADPH + O2 <=> salicylate + NADP+ + H2O 1.14.13

phenylpyruvate <=> enol-phenylpyruvate 5.3.2.1 phenylpyruvate tautomerase
5.3.2.6 2-hydroxymuconate tautomerase


1-phenyl-1,2-propanedione <=> D-Cathinone 2.6.1

phenylacetate + reduced_flavodoxin + O2 <=> 2-hydroxyphenylacetate + flavin + H2O 1.14.14.54 phenylacetate 2-hydroxylase

Cinnamic_acid + NAD+ + H2O <=> benzoate + acetate + NADH + H+ not assigned

H+ + L-phenylalanine <=> 2-Phenylethylamine + CO2 4.1.1.14 valine decarboxylase
4.1.1.19 arginine decarboxylase
4.1.1.25 tyrosine decarboxylase
4.1.1.28 aromatic-L-amino-acid decarboxylase
4.1.1.53 phenylalanine decarboxylase





D-Cathinone <=> D-Cathine not assigned

D-Cathinone <=> (-)-Norephedrine not assigned

phenylpyruvate + H+ <=> phenylacetaldehyde + CO2 4.1.1
4.1.1.1 pyruvate decarboxylase
4.1.1.43 phenylpyruvate decarboxylase
4.1.1.7 benzoylformate decarboxylase
4.1.1.72 branched-chain-2-oxoacid decarboxylase
4.1.1.74 indolepyruvate decarboxylase






phenylacetaldehyde + H2O + NAD+ <=> phenylacetate + NADH + H+ 1.2.1.19 aminobutyraldehyde dehydrogenase
1.2.1.3 aldehyde dehydrogenase (NAD+)
1.2.1.39 phenylacetaldehyde dehydrogenase
1.2.1.5 aldehyde dehydrogenase [NAD(P)+]
1.2.1.8 betaine-aldehyde dehydrogenase





L-phenylalanine + O2 + H2O <=> phenylpyruvate + NH3 + H2O2 + H+ 1.13.12.9 phenylalanine 2-monooxygenase
1.4.3.14 L-lysine oxidase
1.4.3.2 L-amino-acid oxidase



L-phenylalanine + 2-oxoglutarate <=> phenylpyruvate + L-glutamate 2.6.1.1 aspartate transaminase
2.6.1.24 diiodotyrosine transaminase
2.6.1.27 tryptophan 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
2.6.1.60 aromatic-amino-acid---glyoxylate transaminase
2.6.1.64 glutamine---phenylpyruvate transaminase
2.6.1.7 kynurenine---oxoglutarate transaminase
2.6.1.70 aspartate---phenylpyruvate transaminase
2.6.1.79 glutamate---prephenate aminotransferase
2.6.1.9 histidinol-phosphate transaminase













phenylacetyl-CoA + H2O + 1,4-benzoquinone <=> hydroquinone + phenylglyoxylyl-CoA 1.17.5.1 phenylacetyl-CoA dehydrogenase

2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA <=> 2-oxepin-2(3H)-ylideneacetyl-CoA 5.3.3.18 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA isomerase

3-oxo-5,6-dehydrosuberyl-CoA_semialdehyde + NADP+ + H2O <=> 3-oxo-5,6-dehydrosuberyl-CoA + NADPH + H+ 1.2.1.91 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde dehydrogenase

2-hydroxyphenylacetate <=> 2,6-Dihydroxyphenylacetate not assigned

D-phenyllactate + NAD+ <=> phenylpyruvate + NADH + H+ 1.1.1.110 aromatic 2-oxoacid reductase
1.1.1.237 hydroxyphenylpyruvate reductase
1.1.1.26 glyoxylate reductase
1.1.1.27 L-lactate dehydrogenase
1.1.1.272 D-2-hydroxyacid dehydrogenase (NADP+)
1.1.1.28 D-lactate dehydrogenase
1.1.1.337 L-2-hydroxycarboxylate dehydrogenase (NAD+)
1.1.1.345 D-2-hydroxyacid dehydrogenase (NAD+)
1.1.1.37 malate dehydrogenase
1.1.1.79 glyoxylate reductase (NADP+)
1.1.1.96 diiodophenylpyruvate reductase
43380












(2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H2O <=> 2-hydroxy-2,4-pentadienoate + fumarate 3.7.1.14 2-hydroxy-6-oxonona-2,4-dienedioate hydrolase

2-oxepin-2(3H)-ylideneacetyl-CoA + H2O <=> 3-oxo-5,6-dehydrosuberyl-CoA_semialdehyde 3.3.2.12 oxepin-CoA hydrolase

trans-cinnamate <=> 3-hydroxycinnamic_acid not assigned

2-Phenylethylamine + H2O + acceptor <=> phenylacetaldehyde + NH3 + reduced_acceptor 1.4.9.1 methylamine dehydrogenase (amicyanin)
1.4.9.2 aralkylamine dehydrogenase (azurin)
1.4.98



phenylacetyl-CoA + H2O <=> phenylacetate + CoA + H+ 3.1.2
3.1.2.20 acyl-CoA hydrolase
3.1.2.23 4-hydroxybenzoyl-CoA thioesterase
3.1.2.25 phenylacetyl-CoA hydrolase
3.1.2.B5





(3S)-3-hydroxyadipyl-CoA + NAD+ <=> H+ + 3-oxoadipyl-CoA + NADH 1.1.1.157 3-hydroxybutyryl-CoA dehydrogenase
1.1.1.35 3-hydroxyacyl-CoA dehydrogenase


D-Phe + H2O + 1,4-benzoquinone <=> phenylpyruvate + NH3 + hydroquinone 1.4.5.1 D-amino acid dehydrogenase (quinone)

H+ + 3-(3-hydroxyphenyl)propanoate + NADH + O2 <=> 3-(2,3-dihydroxyphenyl)propanoate + H2O + NAD+ 1.14.13.127 3-(3-hydroxyphenyl)propanoate hydroxylase

H2O + hippuric_acid <=> glycine + benzoate 3.4.17.B1
3.5.1.32 hippurate hydrolase
3.5.1.71 N-feruloylglycine deacylase



phenylglyoxylyl-CoA + H2O <=> benzoylformate + H+ + CoA 3.1.2.25 phenylacetyl-CoA hydrolase

3-Phenylpropionic_acid + NAD+ <=> trans-cinnamate + NADH + H+ 1.3.1.31 2-enoate reductase

L-phenylalanine + tetrahydrobiopterin + O2 <=> L-tyrosine + dihydrobiopterin + H2O 1.14.16.1 phenylalanine 4-monooxygenase
1.14.16.4 tryptophan 5-monooxygenase


L-phenylalanine + O2 <=> phenylacetamide + CO2 + H2O 1.11.1.21 catalase-peroxidase
1.13.12.3 tryptophan 2-monooxygenase
1.13.12.9 phenylalanine 2-monooxygenase



D-Phe + 2-oxoglutarate <=> phenylpyruvate + D-glutamate 2.6.1.21 D-amino-acid transaminase

benzoyl-CoA + glycine <=> H+ + hippuric_acid + CoA 2.3.1.13 glycine N-acyltransferase
2.3.1.14 glutamine N-phenylacetyltransferase
2.3.1.71 glycine N-benzoyltransferase



Cinnamic_acid + NADH + O2 + H+ <=> trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylic_acid + NAD+ 1.14.12.19 3-phenylpropanoate dioxygenase

phenylacetyl-CoA + O2 + NADPH + H+ <=> 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP+ + H2O 1.14.13.149 phenylacetyl-CoA 1,2-epoxidase

H+ + Cinnamic_acid + O2 + NADPH <=> H2O + NADP+ + coumaric_acid 1.14.13.14 trans-cinnamate 2-monooxygenase
1.14.14.91 trans-cinnamate 4-monooxygenase


4-hydroxy-2-oxopentanoate <=> 2-oxopent-4-enoate + H2O 4.2.1.80 2-oxopent-4-enoate hydratase

L-phenylalanine + pyruvate <=> phenylpyruvate + L-alanine 2.6.1.12 alanine---oxo-acid transaminase
2.6.1.15 glutamine---pyruvate transaminase
2.6.1.44 alanine---glyoxylate transaminase
2.6.1.51 serine---pyruvate transaminase
2.6.1.57 aromatic-amino-acid transaminase
2.6.1.58 phenylalanine(histidine) transaminase
2.6.1.64 glutamine---phenylpyruvate transaminase







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