Copied!

Pathway Search


Isoquinoline alkaloid biosynthesis

State Icon Reaction EC-Number Confidence maximal confidence score from EnzymeDetector
(S)-1-hydroxy-N-methylcanadine + reduced_flavodoxin + O2 <=> (13S,14R)-1,13-dihydroxy-N-methylcanadine + flavin + H2O 1.14.14.163 (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
–
H+ + O2 + Dihydrosanguinarine <=> H2O2 + sanguinarine 1.3.3.8 tetrahydroberberine oxidase
1.5.3.12 dihydrobenzophenanthridine oxidase
–
–
3,4-Dihydroxybenzaldehyde + tyramine <=> Norcraugsodine + H2O + H+ 4.3.3
–
dopamine + secologanin <=> H2O + N-deacetylisoipecoside 4.3.3.3 deacetylisoipecoside synthase
–
(S)-cis-N-Methylstylopine + reduced_flavodoxin + O2 <=> protopine + flavin + H2O 1.14.14.97 methyltetrahydroprotoberberine 14-monooxygenase
–
dihydrochelirubine + reduced_flavodoxin + O2 <=> 12-hydroxydihydrochelirubine + flavin + H2O 1.14.14.101 dihydrochelirubine 12-monooxygenase
–
S-adenosyl-L-methionine + Columbamine <=> H+ + S-adenosyl-L-homocysteine + palmatine 2.1.1.118 columbamine O-methyltransferase
–
S-adenosyl-L-methionine + (S)-corytuberine <=> S-adenosyl-L-homocysteine + (S)-magnoflorine + H+ 2.1.1.337 reticuline N-methyltransferase
–
S-adenosyl-L-methionine + 12-hydroxydihydrochelirubine <=> H+ + S-adenosyl-L-homocysteine + Dihydromacarpine 2.1.1.120 12-hydroxydihydrochelirubine 12-O-methyltransferase
–
(13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine <=> 3-O-acetyl-4''-O-demethylpapaveroxine + H+ not assigned
 –
1alpha(S)-6-O-methyl-N-deacetylisoipecoside + H2O <=> 1alpha(S)-6-O-methyl-N-deacetylisoipecoside_aglycone + D-glucose 3.2.1
3.2.1.B16
–
–
dopamine + 3-(4-hydroxyphenyl)-propanal <=> (S)-Autumnaline not assigned
 –
S-adenosyl-L-methionine + (S)-Coclaurine <=> H+ + (S)-N-methylcoclaurine + S-adenosyl-L-homocysteine 2.1.1.115 (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
2.1.1.140 (S)-coclaurine-N-methyltransferase
–
–
codeine + 2-oxoglutarate + O2 <=> morphine + formaldehyde + succinate + CO2 1.14.11.32 codeine 3-O-demethylase
–
(S)-cheilanthifoline + reduced_flavodoxin + O2 <=> (S)-Stylopine + flavin + 2 H2O 1.14.19.64 (S)-stylopine synthase
–
(R)-reticuline + NADP+ <=> 1,2-dehydroreticuline + NADPH + H+ 1.5.1.27 1,2-dehydroreticulinium reductase (NADPH)
–
narcotoline_hemiacetal + NAD+ <=> Narcotoline + NADH + H+ 1.1.1.415 noscapine synthase
–
L-tyrosine + H2O + O2 <=> 4-hydroxyphenylpyruvate + NH3 + H2O2 1.4.3.11 L-glutamate oxidase
1.4.3.14 L-lysine oxidase
1.4.3.2 L-amino-acid oxidase
–
–
–
H+ + dihydrochelirubine + O2 <=> chelirubine + H2O2 1.5.3.12 dihydrobenzophenanthridine oxidase
–
S-adenosyl-L-methionine + (S)-norreticuline <=> (S)-Norlaudanine + S-adenosyl-L-homocysteine + H+ 2.1.1
–
(S)-tetrahydrocolumbamine + O2 + H+ <=> Columbamine + H2O2 1.3.3.8 tetrahydroberberine oxidase
–
narcotine_hemiacetal + NAD+ <=> noscapine + NADH + H+ 1.1.1.415 noscapine synthase
–
thebaine + 2-oxoglutarate + O2 <=> oripavine + formaldehyde + succinate + CO2 1.14.11.32 codeine 3-O-demethylase
–
L-tyrosine + O2 + H2O <=> 4-hydroxyphenylacetaldehyde + CO2 + NH3 + H2O2 4.1.1.108 4-hydroxyphenylacetaldehyde synthase
–
4''-O-Desmethylpapaveroxine <=> narcotoline_hemiacetal not assigned
 –
H+ + (-)-tetrahydropalmatine + O2 <=> palmatine + H2O2 1.21.3.3 reticuline oxidase
1.3.3.8 tetrahydroberberine oxidase
–
–
S-adenosyl-L-methionine + (S)-canadine <=> (S)-N-methylcanadine + S-adenosyl-L-homocysteine 2.1.1.122 (S)-tetrahydroprotoberberine N-methyltransferase
–
Dihydrosanguinarine + reduced_flavodoxin + O2 <=> 10-Hydroxydihydrosanguinarine + flavin + H2O 1.14.14.100 dihydrosanguinarine 10-monooxygenase
–
S-adenosyl-L-methionine + N-deacetylisoipecoside <=> 1alpha(S)-6-O-methyl-N-deacetylisoipecoside + S-adenosyl-L-homocysteine + H+ 2.1.1
2.1.1.B84
–
–
neopinone <=> codeinone not assigned
 –
L-tyrosine + O2 <=> L-Dopa 1.10.3.1 catechol oxidase
1.14.18.1 tyrosinase
–
–
S-adenosyl-L-methionine + cephaeline <=> emetine + S-adenosyl-L-homocysteine + H+ 2.1.1
2.1.1.B83
2.1.1.B84
–
–
–
(S)-canadine + O2 + H+ <=> Berberine + H2O2 1.3.3.8 tetrahydroberberine oxidase
–
norbelladine + NADP+ <=> Norcraugsodine + NADPH + H+ 1.4.1
–
4-hydroxyphenylpyruvate + H+ <=> 4-hydroxyphenylacetaldehyde + CO2 4.1.1.72 branched-chain-2-oxoacid decarboxylase
4.1.1.74 indolepyruvate decarboxylase
4.1.1.80 4-hydroxyphenylpyruvate decarboxylase
–
–
–
S-adenosyl-L-methionine + Isoandrocymbine <=> H+ + O-Methylandrocymbine + S-adenosyl-L-homocysteine 2.1.1
–
(S)-reticuline + reduced_flavodoxin + O2 <=> (S)-corytuberine + flavin + 2 H2O 1.14.19.51 (S)-corytuberine synthase
–
S-adenosyl-L-methionine + (S)-Norlaudanosoline <=> S-adenosyl-L-homocysteine + (S)-6-O-methylnorlaudanosoline + H+ 2.1.1.128 (RS)-norcoclaurine 6-O-methyltransferase
–
O2 + (S)-reticuline <=> H+ + H2O2 + (S)-scoulerine 1.21.3.3 reticuline oxidase
–
Demethylisoalangiside <=> Isoalangiside not assigned
 –
Protoemetine <=> Ankorine not assigned
 –
Caranine <=> lycorine not assigned
 –
dopamine + Protoemetine <=> 7''-O-demethylcephaeline + H2O not assigned
 –
4''-O-Methylnorbelladine + reduced_flavodoxin + O2 <=> N-Demethylnarwedine + flavin + 2 H2O 1.14.19
–
Noroxopluviine <=> Caranine not assigned
 –
(4aR,10bS)-Normaritidine <=> crinine not assigned
 –
L-tyrosine + tetrahydrobiopterin + O2 <=> L-Dopa + 4a-hydroxytetrahydrobiopterin 1.14.16.2 tyrosine 3-monooxygenase
–
Demethylalangiside <=> Alangiside not assigned
 –
acetyl-CoA + (13S,14R)-1,13-dihydroxy-N-methylcanadine <=> (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + CoA 2.3.1.285 (13S,14R)-1,13-dihydroxy-N-methylcanadine 13-O-acetyltransferase
–
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + reduced_flavodoxin + O2 <=> (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + flavin + H2O 1.14.14.167 (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
–
S-adenosyl-L-methionine + (S)-6-O-methylnorlaudanosoline <=> S-adenosyl-L-homocysteine + 3''-Hydroxy-N-methyl-(S)-coclaurine 2.1.1.115 (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
–
colcemid <=> Deacetylcolchicine not assigned
 –
(S)-N-methylcanadine + reduced_flavodoxin + O2 <=> Allocryptopine + flavin + H2O 1.14.14.97 methyltetrahydroprotoberberine 14-monooxygenase
–
S-adenosyl-L-methionine + (S)-Stylopine <=> (S)-cis-N-Methylstylopine + S-adenosyl-L-homocysteine 2.1.1
2.1.1.122 (S)-tetrahydroprotoberberine N-methyltransferase
–
–
S-adenosyl-L-methionine + (S)-norreticuline <=> S-adenosyl-L-homocysteine + (S)-reticuline 2.1.1.115 (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
–
4''-O-Desmethyl-3-O-acetylpapaveroxine + H2O <=> 4''-O-Desmethylpapaveroxine + acetate 3.1.1.105 3-O-acetylpapaveroxine carboxylesterase
–
S-adenosyl-L-methionine + (S)-3''-hydroxy-N-methylcoclaurine <=> H+ + S-adenosyl-L-homocysteine + (S)-reticuline 2.1.1.116 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase
2.1.1.128 (RS)-norcoclaurine 6-O-methyltransferase
–
–
NADP+ + salutaridinol <=> H+ + NADPH + salutaridine 1.1.1.248 salutaridine reductase (NADPH)
–
2 (R)-N-methylcoclaurine + reduced_flavodoxin + O2 <=> (R,R)-guattegaumerine + flavin + 2 H2O 1.14.19.66 berbamunine synthase
–
S-adenosyl-L-methionine + 3-O-acetyl-4''-O-demethylpapaveroxine <=> 3-O-acetylpapaveroxine + S-adenosyl-L-homocysteine + H+ 2.1.1.352 3-O-acetyl-4'-O-demethylpapaveroxine 4'-O-methyltransferase
–
S-adenosyl-L-methionine + 7''-O-demethylcephaeline <=> cephaeline + S-adenosyl-L-homocysteine + H+ 2.1.1
2.1.1.B83
2.1.1.B85
–
–
–
S-adenosyl-L-methionine + (S)-6-O-methylnorlaudanosoline <=> S-adenosyl-L-homocysteine + (S)-norreticuline + H+ 2.1.1.116 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase
2.1.1.121 6-O-methylnorlaudanosoline 5'-O-methyltransferase
–
–
(S)-scoulerine + reduced_flavodoxin + O2 <=> (S)-cheilanthifoline + flavin + 2 H2O 1.14.19.65 (S)-cheilanthifoline synthase
–
S-adenosyl-L-methionine + (S)-6-O-methylnorlaudanosoline <=> S-adenosyl-L-homocysteine + (S)-Nororientaline 2.1.1.121 6-O-methylnorlaudanosoline 5'-O-methyltransferase
–
N-deacetylipecoside <=> Demethylalangiside not assigned
 –
thebaine + 2-oxoglutarate + O2 <=> neopinone + formaldehyde + succinate + CO2 1.14.11.31 thebaine 6-O-demethylase
–
4''-O-methylnorbelladine + reduced_flavodoxin + O2 <=> (4aS,10bR)-8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one + flavin + 2 H2O 1.14.19.50 noroxomaritidine synthase
–
Floramultine + S-adenosyl-L-methionine <=> Kreysigine + S-adenosyl-L-homocysteine 2.1.1
–
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + reduced_flavodoxin + O2 <=> Berbamunine + flavin + 2 H2O 1.14.19.66 berbamunine synthase
–
Vittatine <=> (+)-haemanthamine not assigned
 –
dopamine + 4-hydroxyphenylacetaldehyde <=> H2O + (S)-norcoclaurine 4.2.1.78 (S)-norcoclaurine synthase
–
Papaveroxine <=> narcotine_hemiacetal not assigned
 –
NADP+ + codeine <=> H+ + NADPH + codeinone 1.1.1.218 morphine 6-dehydrogenase
1.1.1.247 codeinone reductase (NADPH)
–
–
salutaridinol + acetyl-CoA <=> 7-O-acetylsalutaridinol + CoA 2.3.1.150 salutaridinol 7-O-acetyltransferase
–
(R)-reticuline + reduced_flavodoxin + O2 <=> salutaridine + flavin + 2 H2O 1.14.19.67 salutaridine synthase
–
dopamine + H2O + O2 <=> 3,4-dihydroxyphenylacetaldehyde + NH3 + H2O2 1.4.3.21 primary-amine oxidase
1.4.3.22 diamine oxidase
1.4.3.4 monoamine oxidase
1.4.9.2 aralkylamine dehydrogenase (azurin)
–
–
–
–
4''-O-methylnorbelladine + reduced_flavodoxin + O2 <=> (10bS,4aR)-noroxomaritidine + flavin + 2 H2O 1.14.19.50 noroxomaritidine synthase
–
H+ + L-tyrosine <=> CO2 + tyramine 4.1.1.25 tyrosine decarboxylase
4.1.1.28 aromatic-L-amino-acid decarboxylase
–
–
dopamine + 3,4-dihydroxyphenylacetaldehyde <=> (S)-Norlaudanosoline + H2O 4.2.1.78 (S)-norcoclaurine synthase
–
S-adenosyl-L-methionine + (R)-norreticuline <=> S-adenosyl-L-homocysteine + (R)-N-methylnorreticuline + H+ 2.1.1
2.1.1.115 (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
–
–
NADP+ + morphine <=> NADPH + morphinone + H+ 1.1.1.218 morphine 6-dehydrogenase
1.1.1.247 codeinone reductase (NADPH)
–
–
N-Demethylnarwedine + NADPH <=> Norgalanthamine + NADP+ 1.1.1
–
NAD+ + morphine <=> NADH + morphinone + H+ 1.1.1.218 morphine 6-dehydrogenase
1.1.1.239 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)
–
–
(S)-Coclaurine <=> (S)-6-O-methylnorlaudanosoline not assigned
 –
protopine + reduced_flavodoxin + O2 <=> 6-hydroxyprotopine + flavin + H2O 1.14.14.98 protopine 6-monooxygenase
–
(S)-N-methylcanadine + reduced_flavodoxin + O2 <=> (S)-1-hydroxy-N-methylcanadine + flavin + H2O 1.14.14.166 (S)-N-methylcanadine 1-hydroxylase
–
(S)-reticuline + S-adenosyl-L-methionine <=> laudanine + S-adenosyl-L-homocysteine 2.1.1.291 (R,S)-reticuline 7-O-methyltransferase
–
tyramine + O2 + NADH + H+ <=> dopamine + NAD+ + H2O 1.14.13
1.14.18.1 tyrosinase
–
–
(S)-Autumnaline + NADPH + O2 + H+ <=> Isoandrocymbine + NADP+ + 2 H2O 1.14.21
–
S-adenosyl-L-methionine + Norgalanthamine <=> S-adenosyl-L-homocysteine + galanthamine + H+ 2.1.1
–
O-Methylandrocymbine <=> N-Formyldemecolcine not assigned
 –
(S)-tetrahydropapaverine + 2 O2 <=> papaverine + 2 H2O2 1.3.3.8 tetrahydroberberine oxidase
–
dopamine + secologanin <=> H2O + N-deacetylipecoside 4.3.3.4 deacetylipecoside synthase
–
6-hydroxyprotopine <=> Dihydrosanguinarine + H2O not assigned
 –
(4aS,10bR)-8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one <=> (-)-8-Demethylmaritidine not assigned
 –
(R)-canadine + NADP+ <=> Berberine + NADPH + H+ 1.5.1.31 berberine reductase
–
7-O-acetylsalutaridinol <=> H+ + thebaine + acetate 4.2.99.24 thebaine synthase
–
N-Formyldemecolcine + H2O <=> colcemid + formate 3.5.1
–
S-adenosyl-L-methionine + (S)-scoulerine <=> H+ + S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine 2.1.1.117 (S)-scoulerine 9-O-methyltransferase
–
(4aS,10bR)-8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one <=> Maritinamine not assigned
 –
Deacetylcolchicine + acetyl-CoA <=> H+ + Colchicine + CoA 2.3.1
–
S-adenosyl-L-methionine + (S)-tetrahydrocolumbamine <=> H+ + S-adenosyl-L-homocysteine + (-)-tetrahydropalmatine 2.1.1.117 (S)-scoulerine 9-O-methyltransferase
2.1.1.89 tetrahydrocolumbamine 2-O-methyltransferase
–
–
S-adenosyl-L-methionine + palmatine + NADPH <=> S-adenosyl-L-homocysteine + corydaline + NADP+ 2.1.1.147 corydaline synthase
–
O2 + Columbamine <=> H2O + Berberine 1.21.3.2 columbamine oxidase
–
L-tyrosine + O2 <=> L-Dopa 1.10.3.1 catechol oxidase
1.14.18.1 tyrosinase
–
–
S-adenosyl-L-methionine + norbelladine <=> 4''-O-methylnorbelladine + S-adenosyl-L-homocysteine + H+ 2.1.1.336 norbelladine O-methyltransferase
–
H+ + L-Dopa <=> dopamine + CO2 4.1.1.22 histidine decarboxylase
4.1.1.25 tyrosine decarboxylase
4.1.1.28 aromatic-L-amino-acid decarboxylase
4.1.1.53 phenylalanine decarboxylase
–
–
–
–
S-adenosyl-L-methionine + (S)-norcoclaurine <=> H+ + S-adenosyl-L-homocysteine + (S)-Coclaurine 2.1.1.128 (RS)-norcoclaurine 6-O-methyltransferase
–
(S)-Autumnaline <=> Floramultine not assigned
 –
Narcotoline + S-adenosyl-L-methionine <=> noscapine + S-adenosyl-L-homocysteine 2.1.1.352 3-O-acetyl-4'-O-demethylpapaveroxine 4'-O-methyltransferase
–
N-deacetylisoipecoside <=> Demethylisoalangiside not assigned
 –
oripavine + 2-oxoglutarate + O2 <=> morphinone + formaldehyde + succinate + CO2 1.14.11.31 thebaine 6-O-demethylase
–
S-adenosyl-L-methionine + 10-Hydroxydihydrosanguinarine <=> H+ + S-adenosyl-L-homocysteine + dihydrochelirubine 2.1.1.119 10-hydroxydihydrosanguinarine 10-O-methyltransferase
–
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
–
–
–
–
–
–
–
–
–
–
–
–
(S)-Coclaurine + (R)-N-methylcoclaurine + reduced_flavodoxin + O2 <=> 2''-Norberbamunine + flavin + 2 H2O 1.14.19.66 berbamunine synthase
–
Protoemetine <=> Tubulosine not assigned
 –
(S)-N-methylcoclaurine + reduced_flavodoxin + O2 <=> (S)-3''-hydroxy-N-methylcoclaurine + flavin + H2O 1.14.14.102 N-methylcoclaurine 3'-monooxygenase
–
(10bS,4aR)-noroxomaritidine <=> (4aR,10bS)-Normaritidine not assigned
 –
(S)-tetrahydrocolumbamine + reduced_flavodoxin + O2 <=> (S)-canadine + flavin + 2 H2O 1.14.19.64 (S)-stylopine synthase
1.14.19.68 (S)-canadine synthase
1.14.19.73 (S)-nandinine synthase
–
–
–
(-)-8-Demethylmaritidine <=> Vittatine not assigned
 –
(10bS,4aR)-noroxomaritidine <=> Elwesine not assigned
 –
3-O-acetylpapaveroxine + H2O <=> Papaveroxine + acetate 3.1.1.105 3-O-acetylpapaveroxine carboxylesterase
–
deoxytubulosine <=> alangimarckine not assigned
 –
Protoemetine + tryptamine <=> deoxytubulosine not assigned
 –
p-coumaric_acid <=> 3,4-Dihydroxybenzaldehyde not assigned
 –
(S)-reticuline + reduced_flavodoxin + O2 <=> 1,2-dehydroreticuline + flavin + 2 H2O 1.14.19.54 1,2-dehydroreticuline synthase
–
H+ + Dihydromacarpine + O2 <=> Macarpine + H2O2 1.5.3.12 dihydrobenzophenanthridine oxidase
–
4''-O-Methylnorbelladine <=> Noroxopluviine not assigned
 –
S-adenosyl-L-methionine + (S)-Norlaudanine <=> (S)-tetrahydropapaverine + S-adenosyl-L-homocysteine + H+ 2.1.1
–
1alpha(S)-6-O-methyl-N-deacetylisoipecoside_aglycone <=> Protoemetine not assigned
 –
(S)-reticuline + S-adenosyl-L-methionine <=> laudanine + S-adenosyl-L-homocysteine 2.1.1.291 (R,S)-reticuline 7-O-methyltransferase
–

Visualization of the pathway