Pathway Details

Recommended name

Isoquinoline alkaloid biosynthesis

Alternative names

Reactions

2 L-Tyrosine + O2 <-> 2 L-Dopa

O2 + 2 Columbamine <-> 2 H2O + 2 Berberine

H2O + L-Tyrosine + O2 <-> NH3 + H2O2 + 3-(4-Hydroxyphenyl)pyruvate

L-Tyrosine + O2 <-> H2O + L-Dopa

L-Tyrosine + 2-Oxoglutarate <-> L-Glutamate + 3-(4-Hydroxyphenyl)pyruvate

L-Tyrosine <-> CO2 + Tyramine

L-Dopa <-> CO2 + Dopamine

NADH + H+ + O2 + Tyramine <-> NAD+ + H2O + Dopamine

2 O2 + (S)-Canadine <-> 2 H2O2 + Berberine

3-(4-Hydroxyphenyl)pyruvate <-> CO2 + 4-Hydroxyphenylacetaldehyde

NAD+ + Morphine <-> NADH + H+ + Morphinone

NADP+ + Morphine <-> H+ + NADPH + Morphinone

Morphine <-> Codeine

Morphinone <-> Oripavine

S-Adenosyl-L-methionine + Columbamine <-> S-Adenosyl-L-homocysteine + Palmatine

2 O2 + 5,8,13,13a-Tetrahydrocolumbamine <-> 2 H2O2 + Columbamine

O2 + (S)-Reticuline <-> H2O2 + (S)-Scoulerine

S-Adenosyl-L-methionine + 3'-Hydroxy-N-methyl-(S)-coclaurine <-> S-Adenosyl-L-homocysteine + (S)-Reticuline

Acceptor + (S)-Reticuline <-> Reduced acceptor + 1,2-Dehydroreticuline

2 H2O + NADP+ + (S)-Cheilanthifoline <-> H+ + NADPH + O2 + (S)-Scoulerine

S-Adenosyl-L-methionine + (S)-Scoulerine <-> S-Adenosyl-L-homocysteine + 5,8,13,13a-Tetrahydrocolumbamine

S-Adenosyl-L-methionine + 5,8,13,13a-Tetrahydrocolumbamine <-> S-Adenosyl-L-homocysteine + Tetrahydropalmatine

Dopamine + 3,4-Dihydroxyphenylacetaldehyde <-> H2O + (S)-Norlaudanosoline

H2O + O2 + Dopamine <-> NH3 + H2O2 + 3,4-Dihydroxyphenylacetaldehyde

Dopamine + 4-Hydroxyphenylacetaldehyde <-> H2O + (S)-Norcoclaurine

2 H2O + NADP+ + (S)-Canadine <-> H+ + NADPH + O2 + 5,8,13,13a-Tetrahydrocolumbamine

2 H2O + NADP+ + Stylopine <-> H+ + NADPH + O2 + (S)-Cheilanthifoline

S-Adenosyl-L-methionine + Stylopine <-> S-Adenosyl-L-homocysteine + (S)-cis-N-Methylstylopine

S-Adenosyl-L-methionine + (S)-Coclaurine <-> S-Adenosyl-L-homocysteine + (S)-N-Methylcoclaurine

O2 + (S)-N-Methylcoclaurine <-> H2O + 3'-Hydroxy-N-methyl-(S)-coclaurine

2 H2O + NADP+ + Berbamunine <-> H+ + NADPH + O2 + (S)-N-Methylcoclaurine + (R)-N-Methylcoclaurine

NADP+ + (R)-Reticuline <-> H+ + NADPH + 1,2-Dehydroreticuline

2 H2O + NADP+ + Salutaridine <-> H+ + NADPH + O2 + (R)-Reticuline

NADP+ + 5,6,8,14-Tetradehydro-3,6-dimethoxy-17-methyl-morphinan-4,7-diol <-> H+ + NADPH + Salutaridine

H+ + NADPH + O2 + Protopine <-> H2O + NADP+ + 6-Hydroxyprotopine

Protopine <-> (S)-cis-N-Methylstylopine

6-Hydroxyprotopine <-> Dihydrosanguinarine

H+ + NADPH + O2 + Dihydrosanguinarine <-> H2O + NADP+ + 10-Hydroxydihydrosanguinarine

O2 + Dihydrosanguinarine <-> H2O2 + Sanguinarine

S-Adenosyl-L-methionine + 12-Hydroxydihydrochelirubine <-> S-Adenosyl-L-homocysteine + Dihydromacarpine

O2 + Dihydrochelirubine <-> H2O2 + Chelirubine

S-Adenosyl-L-methionine + 10-Hydroxydihydrosanguinarine <-> S-Adenosyl-L-homocysteine + Dihydrochelirubine

H+ + NADPH + O2 + Dihydrochelirubine <-> H2O + NADP+ + 12-Hydroxydihydrochelirubine

Acetyl-CoA + 5,6,8,14-Tetradehydro-3,6-dimethoxy-17-methyl-morphinan-4,7-diol <-> Coenzyme A + 7-O-Acetylsalutaridinol

O2 + Dihydromacarpine <-> H2O2 + Macarpine

7-O-Acetylsalutaridinol <-> Thebaine

S-Adenosyl-L-methionine + (S)-Norcoclaurine <-> S-Adenosyl-L-homocysteine + (S)-Coclaurine

NADP+ + Codeine <-> H+ + NADPH + 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methoxy-(5_)-morphinan-6-one

7,8-Didehydro-4,5-epoxy-3-methoxy-17-methoxy-(5_)-morphinan-6-one <-> Neopinone

Neopinone <-> Thebaine

Thebaine <-> Oripavine

2 H2O + NADP+ + 2'-Norberbamunine <-> H+ + NADPH + O2 + (R)-N-Methylcoclaurine + (S)-Coclaurine

S-Adenosyl-L-methionine + (S)-Norreticuline <-> S-Adenosyl-L-homocysteine + (S)-Reticuline

S-Adenosyl-L-methionine + (S)-3'-Hydroxycoclaurine <-> S-Adenosyl-L-homocysteine + (S)-Norreticuline

S-Adenosyl-L-methionine + (S)-6-O-Methylnorlaudanosoline <-> S-Adenosyl-L-homocysteine + (S)-Nororientaline

S-Adenosyl-L-methionine + (S)-Norlaudanosoline <-> S-Adenosyl-L-homocysteine + (S)-6-O-Methylnorlaudanosoline

2 H2O + NADP+ + Guattegaumerine <-> H+ + NADPH + O2 + 2 (R)-N-Methylcoclaurine

S-Adenosyl-L-methionine + (R)-Norreticuline <-> S-Adenosyl-L-homocysteine + (R)-Reticuline

H+ + NADPH + O2 + (S)-N-Methylcoclaurine <-> H2O + NADP+ + 3'-Hydroxy-N-methyl-(S)-coclaurine

Secologanin + Dopamine <-> H2O + Deacetylipecoside

Secologanin + Dopamine <-> H2O + Deacetylisoipecoside

Deacetylipecoside <-> Demethylalangiside

Demethylalangiside <-> Alangiside

Deacetylisoipecoside <-> Demethylisoalangiside

Demethylisoalangiside <-> Isoalangiside

Deacetylisoipecoside <-> Protoemetine

Protoemetine <-> Emetine

Protoemetine <-> Cephaeline

Protoemetine <-> Tubulosine

Tryptamine + Protoemetine <-> Deoxytubulosine

Deoxytubulosine <-> Alangimarckine

Protoemetine <-> Ankorine

L-Tyrosine + O2 + Tetrahydrobiopterin <-> L-Dopa + 4a-Hydroxytetrahydrobiopterin

2 NADP+ + (R)-Canadine <-> 2 H+ + 2 NADPH + Berberine

S-Adenosyl-L-methionine + (S)-Reticuline <-> S-Adenosyl-L-homocysteine + Laudanine

S-Adenosyl-L-methionine + (R)-Reticuline <-> S-Adenosyl-L-homocysteine + Laudanine

S-Adenosyl-L-methionine + (S)-Norlaudanosoline <-> S-Adenosyl-L-homocysteine + 6-O-Methylnorlaudanosoline

Classification

Biosynthesis of Other Secondary Metabolites