|
|
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
|
–
|
|
BRENDA:
BR52407
KEGG:
R12067
MetaCyc:
RXN-18458
|
|
|
|
1,4-dihydroxy-6-naphthoate <=> menaquinone
|
not assigned
|
–
|
|
KEGG:
R08596
|
|
|
|
3-geranyl-4-hydroxybenzoate + H+ <=> 2-polyprenylphenol + CO2
|
4.1.1.98
4-hydroxy-3-polyprenylbenzoate decarboxylase
|
–
|
|
BRENDA:
BR51054
KEGG:
R04985
MetaCyc:
RXN-15309
|
|
|
|
phytyl_diphosphate + homogentisate + H+ <=> 2-methyl-6-phytylbenzene-1,4-diol + CO2 + diphosphate
|
2.5.1.115
homogentisate phytyltransferase
|
–
|
|
BRENDA:
BR50958
KEGG:
R07500
MetaCyc:
RXN-2541
|
|
|
|
3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate <=> 2-polyprenyl-6-methoxyphenol + CO2
|
4.1.1
|
–
|
|
KEGG:
R08772
|
|
|
|
2,3-Epoxymenaquinone + dithiothreitol <=> menaquinone + oxidized_dithiothreitol + H2O
|
1.17.4.4
vitamin-K-epoxide reductase (warfarin-sensitive)
|
–
|
|
KEGG:
R09992
|
|
|
|
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
|
–
|
|
BRENDA:
BR50941
KEGG:
R10710
MetaCyc:
RXN-14917
|
|
|
|
beta-tocopherol <=> alpha-tocopherol
|
not assigned
|
–
|
|
KEGG:
R07508
|
|
|
|
2,3-Epoxymenaquinone + peptidyl-4-carboxyglutamate + H2O <=> menaquinol + peptidyl-glutamate + CO2 + O2
|
4.1.1.90
peptidyl-glutamate 4-carboxylase
|
–
|
|
KEGG:
R09991
|
|
|
|
S-adenosyl-L-methionine + delta-tocopherol <=> S-adenosyl-L-homocysteine + beta-tocopherol + H+
|
2.1.1.95
tocopherol C-methyltransferase
|
–
|
|
BRENDA:
BR52800
KEGG:
R07504
MetaCyc:
RXN-2562
|
|
|
|
trans-cinnamate + reduced_flavodoxin + O2 <=> p-coumaric_acid + flavin + H2O
|
1.14.14.91
trans-cinnamate 4-monooxygenase
|
–
|
|
BRENDA:
BR33713
KEGG:
R02253
|
|
|
|
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
|
–
–
–
|
|
BRENDA:
BR63
KEGG:
R01616
MetaCyc:
4-COUMARATE--COA-LIGASE-RXN
SABIO-RK:
1761
|
|
|
|
delta-tocopherol <=> 2-methyl-6-phytylbenzene-1,4-diol
|
5.5.1.24
tocopherol cyclase
|
–
|
|
BRENDA:
BR50791
KEGG:
R07503
MetaCyc:
RXN-2561
|
|
|
|
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
|
–
|
|
BRENDA:
BR49261
KEGG:
R07262
MetaCyc:
RXN-9311
|
|
|
|
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
|
–
|
|
BRENDA:
BR49306
KEGG:
R08769
MetaCyc:
RXN-12160
|
|
|
|
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)
|
–
–
–
–
–
|
|
BRENDA:
BS260199-a;
BS389339
KEGG:
R02964
MetaCyc:
RXN-20991;
RXN0-5388;
RXN0-7123
|
|
|
|
geranylhydroquinone + reduced_flavodoxin + O2 <=> 3''''-hydroxygeranylhydroquinone + flavin + H2O
|
1.14.14.174
geranylhydroquinone 3''-hydroxylase
|
–
|
|
BRENDA:
BR49271
KEGG:
R09042
|
|
|
|
S-adenosyl-L-methionine + delta-tocotrienol <=> S-adenosyl-L-homocysteine + beta-tocotrienol + H+
|
2.1.1.95
tocopherol C-methyltransferase
|
–
|
|
BRENDA:
BR52802
KEGG:
R10492
MetaCyc:
RXN-14919
|
|
|
|
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
|
–
|
|
BRENDA:
BR50940
KEGG:
R10709
MetaCyc:
RXN-2762
|
|
|
|
1,4-dihydroxy-2-naphthoate <=> 2-carboxy-1,4-naphthoquinone
|
not assigned
|
–
|
|
KEGG:
R12254
|
|
|
|
3-geranyl-4-hydroxybenzoate <=> geranylhydroquinone
|
not assigned
|
–
|
|
KEGG:
R09041
|
|
|
|
S-adenosyl-L-methionine + gamma-tocotrienol <=> S-adenosyl-L-homocysteine + alpha-tocotrienol + H+
|
2.1.1.95
tocopherol C-methyltransferase
|
–
|
|
BRENDA:
BR52801
KEGG:
R10491
MetaCyc:
RXN-14918
|
|
|
|
geranyl_diphosphate + 4-hydroxybenzoate <=> 3-geranyl-4-hydroxybenzoate + diphosphate
|
2.5.1.39
4-hydroxybenzoate polyprenyltransferase
2.5.1.93
4-hydroxybenzoate geranyltransferase
|
–
–
|
|
BRENDA:
BR47433
KEGG:
R05000;
R09040
MetaCyc:
RXN-8920
|
|
|
|
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)
|
–
–
|
|
BRENDA:
BS370204-a
KEGG:
R03643;
R03816
MetaCyc:
RXN-19671_WOP
|
|
|
|
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
|
–
|
|
BRENDA:
BR50939
KEGG:
R07501
MetaCyc:
RXN-2542
|
|
|
|
4-(beta-D-glucosyloxy)benzoate + H2O <=> 4-hydroxybenzoate + D-glucose
|
3.2.1
|
–
|
|
KEGG:
R09039
|
|
|
|
geranyl_diphosphate + 1,4-dihydroxy-2-naphthoate <=> a_demethylmenaquinol + diphosphate + CO2
|
2.5.1.74
1,4-dihydroxy-2-naphthoate polyprenyltransferase
|
–
|
|
BRENDA:
BR49120
KEGG:
R10757
|
|
|
|
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
|
–
|
|
BRENDA:
BR49124;
BS427500
KEGG:
R05144
MetaCyc:
RXN-10683
|
|
|
|
gamma-tocopherol <=> 2,3-dimethyl-6-phytylbenzene-1,4-diol
|
5.5.1.24
tocopherol cyclase
|
–
|
|
BRENDA:
BR50792
KEGG:
R07502
MetaCyc:
RXN-2543
|
|
|
|
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)
|
–
–
|
|
BRENDA:
BS188897
KEGG:
R03511
|
|
|
|
4-hydroxyphenylpyruvate + O2 <=> CO2 + homogentisate
|
1.13.11.27
4-hydroxyphenylpyruvate dioxygenase
|
–
|
|
BRENDA:
BR37066
KEGG:
R02521
MetaCyc:
4-HYDROXYPHENYLPYRUVATE-DIOXYGENASE-RXN
SABIO-RK:
2446
|
|
|
|
S-adenosyl-L-methionine + gamma-tocopherol <=> S-adenosyl-L-homocysteine + alpha-tocopherol + H+
|
2.1.1.95
tocopherol C-methyltransferase
|
–
|
|
BRENDA:
BR43934
KEGG:
R07236
MetaCyc:
TOCOPHEROL-O-METHYLTRANSFERASE-RXN
|
|
|
|
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
|
–
|
|
BRENDA:
BR11624;
BS416184
KEGG:
R07263
MetaCyc:
NAPHTHOATE-SYN-RXN
|
|
|
|
(R)-3-(4-hydroxyphenyl)lactate <=> p-coumaric_acid + H2O
|
4.2.1
|
–
|
|
KEGG:
R08766
|
|
|
|
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
|
–
|
|
BRENDA:
BR43874
KEGG:
R08771
MetaCyc:
RXN-11757
|
|
|
|
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
|
–
–
–
|
|
BRENDA:
BR50990;
BS430835
KEGG:
R10668
MetaCyc:
RXN-12346
|
|
|
|
a_demethylmenaquinol + S-adenosyl-L-methionine <=> menaquinol + S-adenosyl-L-homocysteine
|
2.1.1.163
demethylmenaquinone methyltransferase
|
–
|
|
BRENDA:
BR49116
KEGG:
R09736
|
|
|
|
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
|
–
–
|
|
BRENDA:
BR50959
KEGG:
R10708
MetaCyc:
RXN-14929
|
|
|
|
S-adenosyl-L-methionine + 3-[(1-carboxyvinyl)oxy]benzoate + H2O <=> 6-amino-6-deoxyfutalosine + L-methionine + HCO3- + H+
|
2.5.1.120
aminodeoxyfutalosine synthase
|
–
|
|
BRENDA:
BR50963
KEGG:
R10667
MetaCyc:
RXN-15264
|
|
|
|
(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
|
–
|
|
BRENDA:
BR48915
KEGG:
R08166
MetaCyc:
RXN-9310
|
|
|
|
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
|
–
–
–
–
–
–
–
–
–
–
–
–
|
|
BRENDA:
BR47696
KEGG:
R00734
MetaCyc:
TYROSINE-AMINOTRANSFERASE-RXN
SABIO-RK:
1097
|
|
|
|
geranylhydroquinone <=> Dihydroshikonofuran
|
not assigned
|
–
|
|
KEGG:
R09045
|
|
|
|
gamma-tocotrienol <=> 6-geranylgeranyl-2,3-dimethylbenzene-1,4-diol
|
5.5.1.24
tocopherol cyclase
|
–
|
|
BRENDA:
BR50794;
BS427883
KEGG:
R10624
MetaCyc:
RXN-14922
|
|
|
|
3''''-hydroxy-geranylhydroquinone <=> deoxyshikonin
|
not assigned
|
–
|
|
KEGG:
R09043
MetaCyc:
RXN-8923
|
|
|
|
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
|
–
|
|
BRENDA:
BR48908
KEGG:
R08165
MetaCyc:
2.5.1.64-RXN
SABIO-RK:
12389
|
|
|
|
o-succinylbenzoate + CoA + ATP <=> 4-(2''-carboxyphenyl)-4-oxobutyryl-CoA + AMP + diphosphate
|
6.2.1.26
o-succinylbenzoate---CoA ligase
|
–
|
|
BRENDA:
BR48386;
BS363640
KEGG:
R04030
MetaCyc:
O-SUCCINYLBENZOATE-COA-LIG-RXN
|
|
|
|
4-coumaroyl-CoA + CoA + H2O + NAD+ <=> H+ + 4-hydroxybenzoyl-CoA + acetyl-CoA + NADH
|
not assigned
|
–
|
|
KEGG:
R08767
MetaCyc:
RXN3O-1120
|
|
|
|
delta-tocotrienol <=> 6-geranylgeranyl-2-methylbenzene-1,4-diol
|
5.5.1.24
tocopherol cyclase
|
–
|
|
BRENDA:
BR50793
KEGG:
R10623
MetaCyc:
RXN-14921
|
|
|
|
UDP-glucose + 4-hydroxybenzoate <=> 4-(beta-D-glucosyloxy)benzoate + UDP + H+
|
2.4.1.194
4-hydroxybenzoate 4-O-beta-D-glucosyltransferase
|
–
|
|
BRENDA:
BR47409
KEGG:
R01304
MetaCyc:
2.4.1.194-RXN
|
|
|
|
o-succinylbenzoate <=> Spirodilactone + H2O
|
not assigned
|
–
|
|
KEGG:
R05454
|
|
|
|
(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate <=> o-succinylbenzoate + H2O
|
4.2.1.113
o-succinylbenzoate synthase
|
–
|
|
BRENDA:
BR48469;
BS368326
KEGG:
R04031
MetaCyc:
O-SUCCINYLBENZOATE-COA-SYN-RXN
SABIO-RK:
3766
|
|
|
|
2-succinylbenzoyl-CoA <=> Spirodilactone + CoA
|
not assigned
|
–
|
|
KEGG:
R05455
|
|
|
|
2-polyprenylphenol + O2 + NADPH + H+ <=> 2-polyprenyl-6-hydroxyphenol + H2O + NADP+
|
1.14.13.240
2-polyprenylphenol 6-hydroxylase
|
–
|
|
BRENDA:
BR52396
KEGG:
R08768
MetaCyc:
RXN-18459
|
|
|
|
deoxyshikonin <=> shikonin
|
not assigned
|
–
|
|
KEGG:
R09044
|
|
|
|
Dihydroshikonofuran <=> Dihydroechinofuran
|
not assigned
|
–
|
|
KEGG:
R09046
|
|
|
|
chorismate <=> 3-[(1-carboxyvinyl)oxy]benzoate + H2O
|
4.2.1.151
chorismate dehydratase
|
–
|
|
BRENDA:
BR51004
KEGG:
R10666
MetaCyc:
RXN-12345
|
|
|
|
futalosine + H2O <=> dehypoxanthine_futalosine + hypoxanthine
|
3.2.2.26
futalosine hydrolase
|
–
|
|
BRENDA:
BR48967
KEGG:
R08587
MetaCyc:
RXN-9780
|
|
|
|
(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
|
–
–
–
–
–
–
|
|
BRENDA:
BR29263-a;
BS186997
KEGG:
R03337
MetaCyc:
1.1.1.222-RXN_WOP;
HYDROXYPHENYLPYRUVATE-REDUCTASE-RXN
SABIO-RK:
3145
|
|
|
|
chorismate <=> isochorismate
|
5.4.4.2
isochorismate synthase
|
–
|
|
BRENDA:
BR44348
KEGG:
R01717
MetaCyc:
ISOCHORSYN-RXN
SABIO-RK:
1829
|
|
|
|
3-geranyl-4-hydroxybenzoate + O2 <=> 3,4-dihydroxy-5-all-trans-polyprenylbenzoate
|
not assigned
|
–
|
|
KEGG:
R08770
|
|
|
|
demethylphylloquinone + NADPH + H+ <=> demethylphylloquinol + NADP+
|
1.6.5.12
demethylphylloquinone reductase
|
–
|
|
BRENDA:
BR51489
KEGG:
R11061
MetaCyc:
RXN-17007
|
|
|
|
geranyl_diphosphate + 4-hydroxybenzoate <=> 3-geranyl-4-hydroxybenzoate + diphosphate
|
2.5.1.39
4-hydroxybenzoate polyprenyltransferase
2.5.1.93
4-hydroxybenzoate geranyltransferase
|
–
–
|
|
BRENDA:
BR47433
KEGG:
R05000;
R09040
MetaCyc:
RXN-8920
|
|
|
|
S-adenosyl-L-methionine + dehypoxanthine_futalosine <=> cyclic_dehypoxanthinyl_futalosine + L-methionine + 5''-deoxyadenosine + H+
|
1.21.98.1
cyclic dehypoxanthinyl futalosine synthase
|
–
|
|
BRENDA:
BR50934
KEGG:
R08588
MetaCyc:
RXN-10620
|
|
|
|
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
|
–
–
–
|
|
BRENDA:
BR2508
KEGG:
R01301
MetaCyc:
3.1.2.23-RXN
SABIO-RK:
1516
|
|
|
|
S-adenosyl-L-methionine + demethylphylloquinol <=> vitamin_KH2 + S-adenosyl-L-homocysteine + H+
|
2.1.1.329
demethylphylloquinol methyltransferase
|
–
|
|
BRENDA:
BR51848
KEGG:
R04994
MetaCyc:
RXN-7569
|
|
|
|
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
|
–
|
|
BRENDA:
BR49307;
BS410184
KEGG:
R09737
MetaCyc:
RXN-11754
|
|
|
|
cyclic_dehypoxanthinyl_futalosine <=> 1,4-dihydroxy-6-naphthoate
|
1.14
|
–
|
|
KEGG:
R08589
|
|
|
|
(R)-3-(4-hydroxyphenyl)lactate + NADP+ <=> 4-hydroxyphenylpyruvate + NADPH + H+
|
1.1.1.110
aromatic 2-oxoacid reductase
1.1.1.237
hydroxyphenylpyruvate reductase
|
–
–
|
|
BRENDA:
BR29263;
BS370805
KEGG:
R03339
MetaCyc:
1.1.1.222-RXN
|
|
|
|
chorismate <=> 4-hydroxybenzoate + pyruvate
|
4.1.3.40
chorismate lyase
|
–
|
|
BRENDA:
BR48792
KEGG:
R01302
MetaCyc:
CHORPYRLY-RXN
|
|
|
|
6-amino-6-deoxyfutalosine + H2O + H+ <=> futalosine + NH3
|
3.5.4.40
aminodeoxyfutalosine deaminase
|
–
|
|
BRENDA:
BR50991
KEGG:
R10695
MetaCyc:
RXN-14910
|
|
|
|
2-carboxy-1,4-naphthoquinone + phytyl_diphosphate + H+ <=> demethylphylloquinone + diphosphate + CO2
|
2.5.1.130
2-carboxy-1,4-naphthoquinone phytyltransferase
|
–
|
|
BRENDA:
BR51528
KEGG:
R12255
MetaCyc:
RXN-7568
|
|
|
|
nonaprenyl_diphosphate + homogentisate + H+ <=> 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2 + diphosphate
|
2.5.1.117
homogentisate solanesyltransferase
|
–
|
|
BRENDA:
BR50960
KEGG:
R08782
MetaCyc:
RXN-2761
|
|