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Ubiquinone and other terpenoid-quinone biosynthesis

State Icon Reaction EC-Number Confidence maximal confidence score from EnzymeDetector
6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol + O2 + reduced_acceptor <=> 3-demethyubiquinol + H2O + acceptor 1.14.99.60 3-demethoxyubiquinol 3-hydroxylase

1,4-dihydroxy-6-naphthoate <=> menaquinone not assigned

3-geranyl-4-hydroxybenzoate + H+ <=> 2-polyprenylphenol + CO2 4.1.1.98 4-hydroxy-3-polyprenylbenzoate decarboxylase

phytyl_diphosphate + homogentisate + H+ <=> 2-methyl-6-phytylbenzene-1,4-diol + CO2 + diphosphate 2.5.1.115 homogentisate phytyltransferase

3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate <=> 2-polyprenyl-6-methoxyphenol + CO2 4.1.1

2,3-Epoxymenaquinone + dithiothreitol <=> menaquinone + oxidized_dithiothreitol + H2O 1.17.4.4 vitamin-K-epoxide reductase (warfarin-sensitive)

S-adenosyl-L-methionine + 6-geranylgeranyl-2-methylbenzene-1,4-diol <=> S-adenosyl-L-homocysteine + 6-geranylgeranyl-2,3-dimethylbenzene-1,4-diol + H+ 2.1.1.295 2-methyl-6-phytyl-1,4-hydroquinone methyltransferase

beta-tocopherol <=> alpha-tocopherol not assigned

2,3-Epoxymenaquinone + peptidyl-4-carboxyglutamate + H2O <=> menaquinol + peptidyl-glutamate + CO2 + O2 4.1.1.90 peptidyl-glutamate 4-carboxylase

S-adenosyl-L-methionine + delta-tocopherol <=> S-adenosyl-L-homocysteine + beta-tocopherol + H+ 2.1.1.95 tocopherol C-methyltransferase

trans-cinnamate + reduced_flavodoxin + O2 <=> p-coumaric_acid + flavin + H2O 1.14.14.91 trans-cinnamate 4-monooxygenase

p-coumaric_acid + CoA + ATP <=> 4-coumaroyl-CoA + AMP + diphosphate 6.2.1.12 4-coumarate---CoA ligase
6.2.1.2 medium-chain acyl-CoA ligase
6.2.1.30 phenylacetate---CoA ligase



delta-tocopherol <=> 2-methyl-6-phytylbenzene-1,4-diol 5.5.1.24 tocopherol cyclase

1,4-dihydroxy-2-naphthoyl-CoA + H2O <=> H+ + 1,4-dihydroxy-2-naphthoate + CoA 3.1.2.28 1,4-dihydroxy-2-naphthoyl-CoA hydrolase

S-adenosyl-L-methionine + 2-polyprenyl-6-hydroxyphenol <=> 2-polyprenyl-6-methoxyphenol + S-adenosyl-L-homocysteine + H+ 2.1.1.222 2-polyprenyl-6-hydroxyphenol methylase

menaquinone + NADH + H+ <=> menaquinol + NAD+ 1.6.5
1.6.5.2 NAD(P)H dehydrogenase (quinone)
1.6.5.9 NADH:quinone reductase (non-electrogenic)
7.1.1.2 NADH:ubiquinone reductase (H+-translocating)
7.2.1.1 NADH:ubiquinone reductase (Na+-transporting)





geranylhydroquinone + reduced_flavodoxin + O2 <=> 3''''-hydroxygeranylhydroquinone + flavin + H2O 1.14.14.174 geranylhydroquinone 3''-hydroxylase

S-adenosyl-L-methionine + delta-tocotrienol <=> S-adenosyl-L-homocysteine + beta-tocotrienol + H+ 2.1.1.95 tocopherol C-methyltransferase

S-adenosyl-L-methionine + 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol <=> plastoquinol + S-adenosyl-L-homocysteine + H+ 2.1.1.295 2-methyl-6-phytyl-1,4-hydroquinone methyltransferase

1,4-dihydroxy-2-naphthoate <=> 2-carboxy-1,4-naphthoquinone not assigned

3-geranyl-4-hydroxybenzoate <=> geranylhydroquinone not assigned

S-adenosyl-L-methionine + gamma-tocotrienol <=> S-adenosyl-L-homocysteine + alpha-tocotrienol + H+ 2.1.1.95 tocopherol C-methyltransferase

geranyl_diphosphate + 4-hydroxybenzoate <=> 3-geranyl-4-hydroxybenzoate + diphosphate 2.5.1.39 4-hydroxybenzoate polyprenyltransferase
2.5.1.93 4-hydroxybenzoate geranyltransferase


NADH + vitamin_K + H+ <=> NAD+ + vitamin_KH2 1.6.5.2 NAD(P)H dehydrogenase (quinone)
7.1.1.2 NADH:ubiquinone reductase (H+-translocating)


S-adenosyl-L-methionine + 2-methyl-6-phytylbenzene-1,4-diol <=> H+ + 2,3-dimethyl-6-phytylbenzene-1,4-diol + S-adenosyl-L-homocysteine 2.1.1.295 2-methyl-6-phytyl-1,4-hydroquinone methyltransferase

4-(beta-D-glucosyloxy)benzoate + H2O <=> 4-hydroxybenzoate + D-glucose 3.2.1

geranyl_diphosphate + 1,4-dihydroxy-2-naphthoate <=> a_demethylmenaquinol + diphosphate + CO2 2.5.1.74 1,4-dihydroxy-2-naphthoate polyprenyltransferase

peptidyl-4-carboxyglutamate + 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + H+ + H2O <=> CO2 + peptidyl-glutamate + vitamin_KH2 + O2 4.1.1.90 peptidyl-glutamate 4-carboxylase

gamma-tocopherol <=> 2,3-dimethyl-6-phytylbenzene-1,4-diol 5.5.1.24 tocopherol cyclase

2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + dithiothreitol <=> vitamin_K + oxidized_dithiothreitol 1.17.4.4 vitamin-K-epoxide reductase (warfarin-sensitive)
1.17.4.5 vitamin-K-epoxide reductase (warfarin-insensitive)


4-hydroxyphenylpyruvate + O2 <=> CO2 + homogentisate 1.13.11.27 4-hydroxyphenylpyruvate dioxygenase

S-adenosyl-L-methionine + gamma-tocopherol <=> S-adenosyl-L-homocysteine + alpha-tocopherol + H+ 2.1.1.95 tocopherol C-methyltransferase

H+ + 4-(2''-carboxyphenyl)-4-oxobutyryl-CoA <=> 1,4-dihydroxy-2-naphthoyl-CoA + H2O 4.1.3.36 1,4-dihydroxy-2-naphthoyl-CoA synthase

(R)-3-(4-hydroxyphenyl)lactate <=> p-coumaric_acid + H2O 4.2.1

S-adenosyl-L-methionine + 3,4-dihydroxy-5-all-trans-polyprenylbenzoate <=> 3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate + S-adenosyl-L-homocysteine + H+ 2.1.1.114 polyprenyldihydroxybenzoate methyltransferase

6-amino-6-deoxyfutalosine + H2O <=> dehypoxanthine_futalosine + adenine 3.2.2.16 methylthioadenosine nucleosidase
3.2.2.26 futalosine hydrolase
3.2.2.30 aminodeoxyfutalosine nucleosidase



a_demethylmenaquinol + S-adenosyl-L-methionine <=> menaquinol + S-adenosyl-L-homocysteine 2.1.1.163 demethylmenaquinone methyltransferase

geranylgeranyl_diphosphate + homogentisate + H+ <=> diphosphate + 6-geranylgeranyl-2-methylbenzene-1,4-diol + CO2 2.5.1.115 homogentisate phytyltransferase
2.5.1.116 homogentisate geranylgeranyltransferase


S-adenosyl-L-methionine + 3-[(1-carboxyvinyl)oxy]benzoate + H2O <=> 6-amino-6-deoxyfutalosine + L-methionine + HCO3- + H+ 2.5.1.120 aminodeoxyfutalosine synthase

(1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <=> (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate + pyruvate 4.2.99.20 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase

L-tyrosine + 2-oxoglutarate <=> 4-hydroxyphenylpyruvate + L-glutamate 2.6.1.1 aspartate transaminase
2.6.1.2 alanine 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
2.6.1.49 dihydroxyphenylalanine transaminase
2.6.1.5 tyrosine transaminase
2.6.1.57 aromatic-amino-acid transaminase
2.6.1.7 kynurenine---oxoglutarate transaminase
2.6.1.79 glutamate---prephenate aminotransferase
2.6.1.9 histidinol-phosphate transaminase












geranylhydroquinone <=> Dihydroshikonofuran not assigned

gamma-tocotrienol <=> 6-geranylgeranyl-2,3-dimethylbenzene-1,4-diol 5.5.1.24 tocopherol cyclase

3''''-hydroxy-geranylhydroquinone <=> deoxyshikonin not assigned

H+ + isochorismate + 2-oxoglutarate <=> (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2 2.2.1.9 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic-acid synthase

o-succinylbenzoate + CoA + ATP <=> 4-(2''-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate 6.2.1.26 o-succinylbenzoate---CoA ligase

4-coumaroyl-CoA + CoA + H2O + NAD+ <=> H+ + 4-hydroxybenzoyl-CoA + acetyl-CoA + NADH not assigned

delta-tocotrienol <=> 6-geranylgeranyl-2-methylbenzene-1,4-diol 5.5.1.24 tocopherol cyclase

UDP-glucose + 4-hydroxybenzoate <=> 4-(beta-D-glucosyloxy)benzoate + UDP + H+ 2.4.1.194 4-hydroxybenzoate 4-O-beta-D-glucosyltransferase

o-succinylbenzoate <=> Spirodilactone + H2O not assigned

(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate <=> o-succinylbenzoate + H2O 4.2.1.113 o-succinylbenzoate synthase

2-succinylbenzoyl-CoA <=> Spirodilactone + CoA not assigned

2-polyprenylphenol + O2 + NADPH + H+ <=> 2-polyprenyl-6-hydroxyphenol + H2O + NADP+ 1.14.13.240 2-polyprenylphenol 6-hydroxylase

deoxyshikonin <=> shikonin not assigned

Dihydroshikonofuran <=> Dihydroechinofuran not assigned

chorismate <=> 3-[(1-carboxyvinyl)oxy]benzoate + H2O 4.2.1.151 chorismate dehydratase

futalosine + H2O <=> dehypoxanthine_futalosine + hypoxanthine 3.2.2.26 futalosine hydrolase

(R)-3-(4-hydroxyphenyl)lactate + NAD+ <=> 4-hydroxyphenylpyruvate + NADH + H+ 1.1.1.110 aromatic 2-oxoacid reductase
1.1.1.222 (R)-4-hydroxyphenyllactate dehydrogenase
1.1.1.237 hydroxyphenylpyruvate reductase
1.1.1.345 D-2-hydroxyacid dehydrogenase (NAD+)
1.1.1.37 malate dehydrogenase
1.1.1.96 diiodophenylpyruvate reductase






chorismate <=> isochorismate 5.4.4.2 isochorismate synthase

3-geranyl-4-hydroxybenzoate + O2 <=> 3,4-dihydroxy-5-all-trans-polyprenylbenzoate not assigned

demethylphylloquinone + NADPH + H+ <=> demethylphylloquinol + NADP+ 1.6.5.12 demethylphylloquinone reductase

geranyl_diphosphate + 4-hydroxybenzoate <=> 3-geranyl-4-hydroxybenzoate + diphosphate 2.5.1.39 4-hydroxybenzoate polyprenyltransferase
2.5.1.93 4-hydroxybenzoate geranyltransferase


S-adenosyl-L-methionine + dehypoxanthine_futalosine <=> cyclic_dehypoxanthinyl_futalosine + L-methionine + 5''-deoxyadenosine + H+ 1.21.98.1 cyclic dehypoxanthinyl futalosine synthase

4-hydroxybenzoyl-CoA + H2O <=> H+ + 4-hydroxybenzoate + CoA 3.1.2.2 palmitoyl-CoA hydrolase
3.1.2.20 acyl-CoA hydrolase
3.1.2.23 4-hydroxybenzoyl-CoA thioesterase



S-adenosyl-L-methionine + demethylphylloquinol <=> vitamin_KH2 + S-adenosyl-L-homocysteine + H+ 2.1.1.329 demethylphylloquinol methyltransferase

S-adenosyl-L-methionine + 2-methoxy-6-polyprenyl-1,4-benzoquinol <=> 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine + H+ 2.1.1.201 2-methoxy-6-polyprenyl-1,4-benzoquinol methylase

cyclic_dehypoxanthinyl_futalosine <=> 1,4-dihydroxy-6-naphthoate 1.14

(R)-3-(4-hydroxyphenyl)lactate + NADP+ <=> 4-hydroxyphenylpyruvate + NADPH + H+ 1.1.1.110 aromatic 2-oxoacid reductase
1.1.1.237 hydroxyphenylpyruvate reductase


chorismate <=> 4-hydroxybenzoate + pyruvate 4.1.3.40 chorismate lyase

6-amino-6-deoxyfutalosine + H2O + H+ <=> futalosine + NH3 3.5.4.40 aminodeoxyfutalosine deaminase

2-carboxy-1,4-naphthoquinone + phytyl_diphosphate + H+ <=> demethylphylloquinone + diphosphate + CO2 2.5.1.130 2-carboxy-1,4-naphthoquinone phytyltransferase

nonaprenyl_diphosphate + homogentisate + H+ <=> 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2 + diphosphate 2.5.1.117 homogentisate solanesyltransferase

Visualization of the pathway