KEGG   PATHWAY: psom00950
Entry
psom00950                   Pathway                                
Name
Isoquinoline alkaloid biosynthesis - Papaver somniferum (opium poppy)
Description
Isoquinoline alkaloids are tyrosine-derived plant alkaloids with an isoquinoline skeleton. Among them benzylisoquinoline alkaloids form an important group with potent pharmacological activity, including analgesic compounds of morphine and codeine, and anti-infective agents of berberine, palmatine, and magnoflorine. Biosynthesis of isoquinoline alkaloids proceeds via decarboxylation of tyrosine or DOPA to yield dopamine, which together with 4-hydroxyphenylacetaldehyde, an aldehyde derived from tyrosine, is converted to reticuline, an important precursor of various benzylisoquinoline alkaloids.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
psom00950  Isoquinoline alkaloid biosynthesis
psom00950

Module
psom_M00943  Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline [PATH:psom00950]
psom_M00944  Morphine biosynthesis, (S)-reticuline => morphine [PATH:psom00950]
psom_M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine [PATH:psom00950]
psom_M00946  Noscapine biosynthesis, (S)-reticuline => noscapine [PATH:psom00950]
Other DBs
GO: 0033075
Organism
Papaver somniferum (opium poppy) [GN:psom]
Gene
113303925  aspartate aminotransferase, cytoplasmic-like [KO:K14454] [EC:2.6.1.1]
113338059  aspartate aminotransferase, cytoplasmic [KO:K14454] [EC:2.6.1.1]
113348271  aspartate aminotransferase, cytoplasmic-like [KO:K14454] [EC:2.6.1.1]
113349091  aspartate aminotransferase, cytoplasmic-like [KO:K14454] [EC:2.6.1.1]
113302191  aspartate aminotransferase, mitochondrial-like [KO:K14455] [EC:2.6.1.1]
113297005  aspartate aminotransferase, mitochondrial-like [KO:K14455] [EC:2.6.1.1]
113282685  aspartate aminotransferase, chloroplastic-like [KO:K00811] [EC:2.6.1.1]
113355938  aspartate aminotransferase, chloroplastic-like [KO:K00811] [EC:2.6.1.1]
113331727  bifunctional aspartate aminotransferase and glutamate/aspartate-prephenate aminotransferase-like isoform X1 [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
113347486  bifunctional aspartate aminotransferase and glutamate/aspartate-prephenate aminotransferase-like isoform X1 [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
113318550  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113334119  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113335775  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113287557  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113341707  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113335631  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113341807  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113352867  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113353418  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113348796  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113350549  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113308110  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
113340282  uncharacterized protein LOC113340282 [KO:K13382] [EC:3.5.99.14]
113277377  S-norcoclaurine synthase 1-like [KO:K13382] [EC:3.5.99.14]
113326100  uncharacterized protein LOC113326100 [KO:K13382] [EC:3.5.99.14]
113283898  (RS)-norcoclaurine 6-O-methyltransferase [KO:K13383] [EC:2.1.1.128]
113294670  (S)-coclaurine N-methyltransferase [KO:K13384] [EC:2.1.1.115 2.1.1.140]
113318496  (S)-coclaurine N-methyltransferase-like isoform X1 [KO:K13384] [EC:2.1.1.115 2.1.1.140]
113314340  (S)-N-methylcoclaurine 3'-hydroxylase isozyme 1 [KO:K13385] [EC:1.14.14.102]
113339850  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2 [KO:K13386] [EC:2.1.1.116]
113326743  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2-like [KO:K13386] [EC:2.1.1.116]
113294323  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 1-like [KO:K13386] [EC:2.1.1.116]
113327792  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 1 [KO:K13386] [EC:2.1.1.116]
113339870  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2-like [KO:K13386] [EC:2.1.1.116]
113326977  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2-like [KO:K13386] [EC:2.1.1.116]
113328438  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2-like [KO:K13386] [EC:2.1.1.116]
113353561  3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase 2-like [KO:K13386] [EC:2.1.1.116]
113328355  norreticuline-7-O-methyltransferase [KO:K22088] [EC:2.1.1.-]
113274966  berberine bridge enzyme-like 8 [KO:K22089] [EC:1.3.3.8]
113303200  berberine bridge enzyme-like 8 [KO:K22089] [EC:1.3.3.8]
113318085  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113318091  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113325989  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113326693  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113310294  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113313874  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113288662  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113330934  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113287664  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113320211  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113284640  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113284645  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113306281  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113339778  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113288165  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113339945  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113276280  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113276320  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113291222  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113335035  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113321283  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113304358  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113317407  aureusidin synthase-like [KO:K00422] [EC:1.10.3.1]
113345373  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113322011  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113291768  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113344239  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113344391  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113276494  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113278524  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113290244  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113349439  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113358933  polyphenol oxidase I, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113353825  polyphenol oxidase, chloroplastic-like [KO:K00422] [EC:1.10.3.1]
113300024  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113300033  tyrosine/DOPA decarboxylase 5-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113300401  tyrosine decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113317135  tyrosine decarboxylase 1-like isoform X1 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113317142  tyrosine/DOPA decarboxylase 2-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113335689  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113336160  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113336161  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113336168  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113336188  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113336203  tyrosine/DOPA decarboxylase 1 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113275368  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113282258  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113315171  tyrosine decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113285898  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113289816  tyrosine/DOPA decarboxylase 5 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113300565  tyrosine/DOPA decarboxylase 2 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113328604  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113328798  tryptophan decarboxylase TDC2-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113342821  tryptophan decarboxylase TDC2-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113286311  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113286782  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113286784  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113286785  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113282799  tyrosine/DOPA decarboxylase 3 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113348283  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113349848  tyrosine decarboxylase 1-like isoform X1 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113355837  tyrosine/DOPA decarboxylase 3-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113347922  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113349080  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113349082  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113355340  tyrosine/DOPA decarboxylase 1-like [KO:K01593] [EC:4.1.1.28 4.1.1.105]
113344052  uncharacterized protein LOC113344052 [KO:K00276] [EC:1.4.3.21]
113347115  primary amine oxidase 1-like [KO:K00276] [EC:1.4.3.21]
113346310  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113282356  uncharacterized protein LOC113282356 [KO:K00276] [EC:1.4.3.21]
113296430  primary amine oxidase 1-like [KO:K00276] [EC:1.4.3.21]
113304618  uncharacterized protein LOC113304618 [KO:K00276] [EC:1.4.3.21]
113340990  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113275136  uncharacterized protein LOC113275136 [KO:K00276] [EC:1.4.3.21]
113305321  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113317514  uncharacterized protein LOC113317514 isoform X1 [KO:K00276] [EC:1.4.3.21]
113335942  uncharacterized protein LOC113335942 [KO:K00276] [EC:1.4.3.21]
113276172  uncharacterized protein LOC113276172 isoform X1 [KO:K00276] [EC:1.4.3.21]
113275220  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113275222  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113305398  primary amine oxidase-like [KO:K00276] [EC:1.4.3.21]
113350725  primary amine oxidase 2-like [KO:K00276] [EC:1.4.3.21]
113277829  N-methyltransferase 4 [KO:K21580] [EC:2.1.1.337]
113324773  N-methyltransferase 4 [KO:K21580] [EC:2.1.1.337]
113344288  N-methyltransferase 4-like [KO:K21580] [EC:2.1.1.337]
113309783  N-methyltransferase 4-like [KO:K21580] [EC:2.1.1.337]
113319724  N-methyltransferase 4-like isoform X1 [KO:K21580] [EC:2.1.1.337]
113300499  N-methyltransferase 4-like isoform X1 [KO:K21580] [EC:2.1.1.337]
113338827  (R,S)-reticuline 7-O-methyltransferase [KO:K13390] [EC:2.1.1.291]
113322712  bifunctional protein STORR [KO:K22093] [EC:1.14.19.54 1.5.1.27]
113321914  salutaridine synthase [KO:K13391] [EC:1.14.19.67]
113339274  salutaridine synthase-like [KO:K13391] [EC:1.14.19.67]
113340174  salutaridine reductase isoform X1 [KO:K13392] [EC:1.1.1.248]
113322262  salutaridine reductase [KO:K13392] [EC:1.1.1.248]
113340083  salutaridinol 7-O-acetyltransferase-like [KO:K13393] [EC:2.3.1.150]
113321357  salutaridinol 7-O-acetyltransferase [KO:K13393] [EC:2.3.1.150]
113340172  major latex protein 149-like isoform X1 [KO:K01742] [EC:4.2.99.24]
113322169  major latex protein 149-like [KO:K01742] [EC:4.2.99.24]
113311621  codeine O-demethylase [KO:K14975] [EC:1.14.11.32]
113311630  codeine O-demethylase [KO:K14975] [EC:1.14.11.32]
113311635  codeine O-demethylase-like [KO:K14975] [EC:1.14.11.32]
113347787  thebaine 6-O-demethylase-like [KO:K14976] [EC:1.14.11.31]
113347789  thebaine 6-O-demethylase [KO:K14976] [EC:1.14.11.31]
113347786  thebaine 6-O-demethylase-like [KO:K14976] [EC:1.14.11.31]
113347790  thebaine 6-O-demethylase-like [KO:K14976] [EC:1.14.11.31]
113272570  thebaine 6-O-demethylase-like [KO:K14976] [EC:1.14.11.31]
113347785  thebaine 6-O-demethylase-like [KO:K14976] [EC:1.14.11.31]
113328200  NADPH-dependent codeinone reductase 1-5 [KO:K13394] [EC:1.1.1.247]
113328201  NADPH-dependent codeinone reductase 1-5 [KO:K13394] [EC:1.1.1.247]
113293958  NADPH-dependent codeinone reductase 1-4-like [KO:K13394] [EC:1.1.1.247]
113294469  NADPH-dependent codeinone reductase 1-4 [KO:K13394] [EC:1.1.1.247]
113325420  major latex protein 15-like [KO:K01828] [EC:5.3.3.24]
113320582  major latex protein 15-like [KO:K01828] [EC:5.3.3.24]
113323967  MLP-like protein 34 [KO:K01828] [EC:5.3.3.24]
113303821  reticuline oxidase-like [KO:K00307] [EC:1.21.3.3]
113317935  reticuline oxidase [KO:K00307] [EC:1.21.3.3]
113347886  cheilanthifoline synthase [KO:K21070] [EC:1.14.19.65]
113349486  cheilanthifoline synthase-like [KO:K21070] [EC:1.14.19.65]
113349389  cheilanthifoline synthase-like [KO:K21070] [EC:1.14.19.65]
113347890  (S)-stylopine synthase 1-like [KO:K13395] [EC:1.14.19.64 1.14.19.68 1.14.19.73]
113322097  trifunctional (S)-stylopine synthase/(S)-nandinine synthase/(S)-canadine synthase-like [KO:K13395] [EC:1.14.19.64 1.14.19.68 1.14.19.73]
113295244  (S)-tetrahydroprotoberberine N-methyltransferase [KO:K13396] [EC:2.1.1.122]
113323066  (S)-tetrahydroprotoberberine N-methyltransferase 1-like [KO:K13396] [EC:2.1.1.122]
113320885  (S)-tetrahydroprotoberberine N-methyltransferase 1-like isoform X1 [KO:K13396] [EC:2.1.1.122]
113317972  (S)-tetrahydroprotoberberine N-methyltransferase-like [KO:K13396] [EC:2.1.1.122]
113322396  bifunctional protein STORR-like [KO:K20621] [EC:1.14.14.166]
113322152  methyltetrahydroprotoberberine 14-monooxygenase-like [KO:K22094] [EC:1.14.14.163]
113273664  salutaridinol 7-O-acetyltransferase-like [KO:K22095] [EC:2.3.1.285]
113303870  salutaridinol 7-O-acetyltransferase-like [KO:K22095] [EC:2.3.1.285]
113322791  salutaridinol 7-O-acetyltransferase-like [KO:K22095] [EC:2.3.1.285]
113322295  methyltetrahydroprotoberberine 14-monooxygenase-like [KO:K22096] [EC:1.14.14.167]
113322812  carboxylesterase 1-like [KO:K22097] [EC:3.1.1.105]
113323289  carboxylesterase 1-like [KO:K22097] [EC:3.1.1.105]
113275170  vestitone reductase-like [KO:K22098] [EC:1.1.1.415]
113322802  (RS)-norcoclaurine 6-O-methyltransferase-like [KO:K23157] [EC:2.1.1.352]
113322330  (RS)-norcoclaurine 6-O-methyltransferase-like [KO:K23158]
113322770  methyltetrahydroprotoberberine 14-monooxygenase [KO:K21692] [EC:1.14.14.97]
113330723  protopine 6-monooxygenase [KO:K21693] [EC:1.14.14.98]
113357146  protopine 6-monooxygenase-like [KO:K21693] [EC:1.14.14.98]
113322507  (S)-scoulerine 9-O-methyltransferase-like [KO:K13397] [EC:2.1.1.117]
113293137  (S)-scoulerine 9-O-methyltransferase-like isoform X1 [KO:K13397] [EC:2.1.1.117]
113362144  (S)-scoulerine 9-O-methyltransferase-like isoform X1 [KO:K13397] [EC:2.1.1.117]
Compound
C00082  L-Tyrosine
C00355  3,4-Dihydroxy-L-phenylalanine
C00483  Tyramine
C00757  Berberine
C00811  4-Coumarate
C01179  3-(4-Hydroxyphenyl)pyruvate
C01516  Morphine
C01735  Morphinone
C01795  Columbamine
C01852  Secologanin
C02105  (S)-Reticuline
C02106  (S)-Scoulerine
C02134  Allocryptopine
C02890  Tetrahydropalmatine
C02915  (S)-cis-N-Methylcanadine
C02916  (S)-Norlaudanosoline
C03329  (S)-Canadine
C03758  Dopamine
C03765  4-Hydroxyphenylacetaldehyde
C04043  3,4-Dihydroxyphenylacetaldehyde
C04118  Isocorypalmine
C05174  (S)-Cheilanthifoline
C05175  Stylopine
C05176  (S)-N-Methylcoclaurine
C05177  Berbamunine
C05178  (R)-Reticuline
C05179  Salutaridine
C05189  Protopine
C05190  6-Hydroxyprotopine
C05191  Dihydrosanguinarine
C05193  12-Hydroxydihydrochelirubine
C05194  Dihydrochelirubine
C05202  3'-Hydroxy-N-methyl-(S)-coclaurine
C05220  Salutaridinol
C05243  (R)-N-Methylcoclaurine
C05247  10-Hydroxydihydrosanguinarine
C05315  Palmatine
C05316  Dihydromacarpine
C05322  7-O-Acetylsalutaridinol
C06160  (S)-Norcoclaurine
C06161  (S)-Coclaurine
C06162  Sanguinarine
C06163  (S)-cis-N-Methylstylopine
C06165  Macarpine
C06167  1,2-Dehydroreticuline
C06171  Codeinone
C06172  Neopinone
C06173  Thebaine
C06174  Codeine
C06175  Oripavine
C06327  Chelirubine
C06511  Guattegaumerine
C06512  2'-Norberbamunine
C06516  (R)-Norreticuline
C06517  (S)-6-O-Methylnorlaudanosoline
C06518  (S)-Nororientaline
C06520  (S)-Norreticuline
C06533  Papaverine
C06546  Mescaline
C07304  Deacetylisoipecoside
C07307  Deacetylipecoside
C07547  Tubocurarine
C07592  Colchicine
C08521  Caranine
C08526  Galanthamine
C08527  Haemanthamine
C08532  Lycorine
C09248  Tubulosine
C09328  Alangimarckine
C09330  Alangiside
C09337  Ankorine
C09390  Cephaeline
C09421  Emetine
C09464  Ipecoside
C09541  (S)-Isoboldine
C09581  Magnoflorine
C09592  alpha-Narcotine
C09593  Narcotoline
C09654  (+)-Tetrandrine
C11250  Demecolcine
C11813  Demethylalangiside
C11814  Demethylisoalangiside
C11815  Isoalangiside
C11816  Protoemetine
C11817  Deoxytubulosine
C11818  (R)-Canadine
C12162  Crinine
C12173  Norgalanthamine
C12180  (-)-8-Demethylmaritidine
C12193  Vittatine
C12231  Anhalamine
C15530  Corydaline
C16700  3,4-Dihydroxybenzaldehyde
C16701  Norbelladine
C16702  4'-O-Methylnorbelladine
C16703  N-Demethylnarwedine
C16704  Anhalonidine
C16705  Anhalonine
C16706  4-Hydroxydihydrocinnamaldehyde
C16707  (S)-Autumnaline
C16708  Isoandrocymbine
C16709  O-Methylandrocymbine
C16710  N-Formyldemecolcine
C16712  Deacetylcolchicine
C16713  Floramultine
C16714  Kreysigine
C17591  (S)-Corytuberine
C17592  Laudanine
C20297  Narcotine hemiacetal
C20299  Papaveroxine
C21405  (4aS,10bR)-Noroxomaritidine
C21406  (4aR,10bS)-Noroxomaritidine
C21566  6-O-Methyldeacetylisoipecoside
C21583  6-O-Methyl-N-deacetylisoipecoside aglycon
C21584  7'-O-Dmethylcephaeline
C21586  (S)-1-Hydroxy-cis-N-methylcanadine
C21587  (13S,14R)-1,13-Dihydroxy-cis-N-methylcanadine
C21588  (13S,14R)-13-O-Acetyl-1-hydroxy-cis-N-methylcanadine
C21589  (13S,14R)-13-O-Acetyl-1,8-dihydroxy-cis-N-methylcanadine
C21590  4'-O-Desmethyl-3-O-acetylpapaveroxine
C21591  3-O-Acetylpapaveroxine
C21599  4'-O-Desmethylpapaveroxine
C21600  Narcotoline hemiacetal
C21630  (S)-Norlaudanine
C21631  (S)-Tetrahydropapaverine
C21633  Noroxopluviine
C21634  Norcraugsodine
C21635  (4aR,10bS)-Normaritidine
C21637  Elwesine
C21639  Maritinamine
C22694  Ipecoside aglycone
Reference
PMID:10811648
  Authors
Morishige T, Tsujita T, Yamada Y, Sato F
  Title
Molecular characterization of the S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica.
  Journal
J Biol Chem 275:23398-405 (2000)
DOI:10.1074/jbc.M002439200
Reference
PMID:12423366
  Authors
Morishige T, Dubouzet E, Choi KB, Yazaki K, Sato F
  Title
Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells.
  Journal
Eur J Biochem 269:5659-67 (2002)
DOI:10.1046/j.1432-1033.2002.03275.x
Reference
PMID:14675446
  Authors
Ounaroon A, Decker G, Schmidt J, Lottspeich F, Kutchan TM
  Title
(R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy.
  Journal
Plant J 36:808-19 (2003)
DOI:10.1046/j.1365-313X.2003.01928.x
Reference
PMID:18230623
  Authors
Ikezawa N, Iwasa K, Sato F
  Title
Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells.
  Journal
J Biol Chem 283:8810-21 (2008)
DOI:10.1074/jbc.M705082200
Reference
PMID:18476877
  Authors
Facchini PJ, De Luca V
  Title
Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants.
  Journal
Plant J 54:763-84 (2008)
DOI:10.1111/j.1365-313X.2008.03438.x
Reference
PMID:18492807
  Authors
Minami H, Kim JS, Ikezawa N, Takemura T, Katayama T, Kumagai H, Sato F
  Title
Microbial production of plant benzylisoquinoline alkaloids.
  Journal
Proc Natl Acad Sci U S A 105:7393-8 (2008)
DOI:10.1073/pnas.0802981105
Reference
  Authors
Rueffer M, Bauer W, Zenk MH.
  Title
The formation of corydaline and related alkaloids in Corydalis cava in vivo and in vitro.
  Journal
Can J Chem 72:170-175 (1994)
DOI:10.1139/v94-026
Reference
  Authors
Sekine Y, Crevelling C, Bell M, Brossi A.
  Title
Mammalian alkaloids: O-methylation of (+-)-norcoclaurine-1-carboxylic acid and related isoquinolines including (S)- and (R)-norcoclaurine with 14C-labeled S-adenosyl-L-methionine in presence of mammalian catechol O-methyltransferase.
  Journal
Helv Chim Acta 73:426-432 (1990)
DOI:10.1002/hlca.19900730222
Reference
  Authors
De-Eknamkul W, Tanahashi T, Zenk MH.
  Title
Enzymic 10-hydroxylation and 10-O-methylation of dihydrosanguinarine in dihydrochelirubine formation by Eschscholtzia.
  Journal
Phytochemistry 31:2713-2717 (1992)
DOI:10.1016/0031-9422(92)83617-8
Reference
  Authors
Kammerer L, De-Eknamkul W, Zenk MH.
  Title
Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum.
  Journal
Phytochemistry 36:1409-1416 (1994)
DOI:10.1016/S0031-9422(00)89732-0
Reference
PMID:24241413
  Authors
Schumacher HM, Zenk MH
  Title
Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures.
  Journal
Plant Cell Rep 7:43-6 (1988)
DOI:10.1007/BF00272975
Reference
  Authors
Rueffer M, Zenk MH.
  Title
Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans.
  Journal
Tetrahedron Lett 28:5307-5310 (1987)
DOI:10.1016/S0040-4039(00)96715-7
Related
pathway
psom00350  Tyrosine metabolism
psom00360  Phenylalanine metabolism
psom00400  Phenylalanine, tyrosine and tryptophan biosynthesis
psom00902  Monoterpenoid biosynthesis
KO pathway
ko00950   
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