ENTRY R04691 Reaction DEFINITION Stylopine + S-Adenosyl-L-methionine <=> (S)-cis-N-Methylstylopine + S-Adenosyl-L-homocysteine EQUATION C05175 + C00019 <=> C06163 + C00021 RCLASS RC00003 C00019_C00021 RC01197 C05175_C06163 ENZYME 2.1.1.122 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00945 Sanguinarine biosynthesis, (S)-reticuline => sanguinarine BRITE Enzymatic reactions [BR:br08201] 2. Transferase reactions 2.1 Transferring one-carbon groups 2.1.1 Methyltransferases 2.1.1.122 R04691 Stylopine + S-Adenosyl-L-methionine <=> (S)-cis-N-Methylstylopine + S-Adenosyl-L-homocysteine IUBMB reaction hierarchy [BR:br08202] 2. Transferase reactions 2.1.1.122 R04716 (S)-Tetrahydroprotoberberine <=> (S)-cis-N-Methyl-7,8,13,14-tetrahydroprotoberberine R04691 Stylopine <=> (S)-cis-N-Methylstylopine ORTHOLOGY K13396 (S)-tetrahydroprotoberberine N-methyltransferase [EC:2.1.1.122] DBLINKS RHEA: 75978 /// ENTRY R04692 Reaction NAME S-adenosyl-L-methionine:(S)-coclaurine-N-methyltransferase DEFINITION S-Adenosyl-L-methionine + (S)-Coclaurine <=> S-Adenosyl-L-homocysteine + (S)-N-Methylcoclaurine + H+ EQUATION C00019 + C06161 <=> C00021 + C05176 + C00080 RCLASS RC00003 C00019_C00021 RC01198 C05176_C06161 ENZYME 2.1.1.115 2.1.1.140 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00943 Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline BRITE Enzymatic reactions [BR:br08201] 2. Transferase reactions 2.1 Transferring one-carbon groups 2.1.1 Methyltransferases 2.1.1.115 R04692 S-Adenosyl-L-methionine + (S)-Coclaurine <=> S-Adenosyl-L-homocysteine + (S)-N-Methylcoclaurine + H+ 2.1.1.140 R04692 S-Adenosyl-L-methionine + (S)-Coclaurine <=> S-Adenosyl-L-homocysteine + (S)-N-Methylcoclaurine + H+ ORTHOLOGY K13384 (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase [EC:2.1.1.115 2.1.1.140] DBLINKS RHEA: 17412 /// ENTRY R04693 Reaction NAME monophenol,L-dopa:oxygen oxidoreductase DEFINITION (S)-N-Methylcoclaurine + Oxygen + Reduced acceptor <=> 3'-Hydroxy-N-methyl-(S)-coclaurine + H2O + Acceptor EQUATION C05176 + C00007 + C00030 <=> C05202 + C00001 + C00028 COMMENT Ref:1. Meth Enzymol 1987; 142: 165-169 RCLASS RC00046 C05176_C05202 ENZYME 1.14.18.1 BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen 1.14.18 With another compound as one donor, and incorporation of one atom of oxygen into the other donor 1.14.18.1 R04693 (S)-N-Methylcoclaurine + Oxygen + Reduced acceptor <=> 3'-Hydroxy-N-methyl-(S)-coclaurine + H2O + Acceptor ORTHOLOGY K00505 tyrosinase [EC:1.14.18.1] /// ENTRY R04694 Reaction NAME (S)-N-methylcoclaurine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (C-O phenol-coupling) DEFINITION (S)-N-Methylcoclaurine + (R)-N-Methylcoclaurine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Berbamunine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O EQUATION C05176 + C05243 + C03024 + C00007 <=> C05177 + C03161 + 2 C00001 RCLASS RC00878 C05176_C05177 RC01199 C05177_C05243 ENZYME 1.14.19.66 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01110 Biosynthesis of secondary metabolites BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen 1.14.19 With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water 1.14.19.66 R04694 (S)-N-Methylcoclaurine + (R)-N-Methylcoclaurine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Berbamunine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O ORTHOLOGY K13387 berbamunine synthase [EC:1.14.19.66] DBLINKS RHEA: 23579 /// ENTRY R04695 Reaction NAME (R)-reticuline:NADP+ oxidoreductase DEFINITION (R)-Reticuline + NADP+ <=> 1,2-Dehydroreticuline + NADPH EQUATION C05178 + C00006 <=> C06167 + C00005 RCLASS RC00001 C00005_C00006 RC01200 C05178_C06167 ENZYME 1.5.1.27 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00944 Morphine biosynthesis, (S)-reticuline => morphine BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.5 Acting on the CH-NH group of donors 1.5.1 With NAD+ or NADP+ as acceptor 1.5.1.27 R04695 (R)-Reticuline + NADP+ <=> 1,2-Dehydroreticuline + NADPH ORTHOLOGY K22093 1,2-dehydroreticuline synthase/reductase [EC:1.14.19.54 1.5.1.27] DBLINKS RHEA: 17572 /// ENTRY R04696 Reaction NAME (R)-reticuline,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (C-C phenol-coupling) DEFINITION (R)-Reticuline + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Salutaridine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O EQUATION C05178 + C03024 + C00007 <=> C05179 + C03161 + 2 C00001 RCLASS RC02285 C05178_C05179 ENZYME 1.14.19.67 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00944 Morphine biosynthesis, (S)-reticuline => morphine BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen 1.14.19 With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water 1.14.19.67 R04696 (R)-Reticuline + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Salutaridine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O ORTHOLOGY K13391 salutaridine synthase [EC:1.14.19.67] DBLINKS RHEA: 17716 /// ENTRY R04697 Reaction NAME salutaridinol:NADP+ 7-oxidoreductase DEFINITION Salutaridinol + NADP+ <=> Salutaridine + NADPH + H+ EQUATION C05220 + C00006 <=> C05179 + C00005 + C00080 RCLASS RC00001 C00005_C00006 RC01202 C05179_C05220 ENZYME 1.1.1.248 PATHWAY rn00950 Isoquinoline alkaloid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00944 Morphine biosynthesis, (S)-reticuline => morphine BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.1 Acting on the CH-OH group of donors 1.1.1 With NAD+ or NADP+ as acceptor 1.1.1.248 R04697 Salutaridinol + NADP+ <=> Salutaridine + NADPH + H+ ORTHOLOGY K13392 salutaridine reductase (NADPH) [EC:1.1.1.248] DBLINKS RHEA: 10111 /// ENTRY R03876 Reaction DEFINITION ATP + Ubiquitin + Protein lysine <=> AMP + Diphosphate + Protein N-ubiquityllysine EQUATION C00002 + C00496 + C02188 <=> C00020 + C00013 + C03635 /// ENTRY R06209 Reaction DEFINITION Starch(n+m) + H2O <=> Starch(n) + Starch(m) EQUATION G10545(n+m) + C00001 <=> G10545(n) + G10545(m) REMARK Same as: R02108 ENZYME 3.2.1.1 BRITE Enzymatic reactions [BR:br08201] 3. Hydrolase reactions 3.2 Glycosylases 3.2.1 Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds 3.2.1.1 R06209 Starch(n+m) + H2O <=> Starch(n) + Starch(m) /// ENTRY C00099 Compound NAME beta-Alanine; 3-Aminopropionic acid; 3-Aminopropanoate FORMULA C3H7NO2 EXACT_MASS 89.0477 MOL_WEIGHT 89.09 REMARK Same as: D07561 REACTION R00489 R00904 R00905 R00906 R00907 R00908 R00909 R00910 R00911 R00912 R00913 R00914 R00915 R00916 R00917 R01164 R01166 R02473 R02474 R02741 R03286 R03288 R03935 R09379 R09648 R10821 PATHWAY map00240 Pyrimidine metabolism map00410 beta-Alanine metabolism map00640 Propanoate metabolism map00770 Pantothenate and CoA biosynthesis map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites map01240 Biosynthesis of cofactors map04080 Neuroactive ligand-receptor interaction map04974 Protein digestion and absorption MODULE M00046 Pyrimidine degradation, uracil => beta-alanine, thymine => 3-aminoisobutanoate M00119 Pantothenate biosynthesis, valine/L-aspartate => pantothenate M00913 Pantothenate biosynthesis, 2-oxoisovalerate/spermine => pantothenate ENZYME 1.2.1.3 1.2.1.5 1.2.1.19 1.5.1.26 2.6.1.18 2.6.1.19 2.6.1.55 2.6.1.120 2.8.3.- 3.4.13.4 3.4.13.5 3.4.13.18 3.4.13.20 3.5.1.6 3.5.1.21 3.5.1.22 3.5.1.100 3.5.3.17 4.1.1.11 4.1.1.15 6.3.2.1 6.3.2.11 6.3.2.23 6.3.2.36 6.3.2.44 BRITE Compounds with biological roles [BR:br08001] Peptides Amino acids Other amino acids C00099 beta-Alanine Amines Biogenic amines C00099 beta-Alanine DBLINKS CAS: 107-95-9 PubChem: 3399 ChEBI: 16958 KNApSAcK: C00001333 PDB-CCD: BAL NIKKAJI: J4.070C ATOM 6 1 C1b C 25.6778 -16.8919 2 C6a C 24.4732 -16.1936 3 C1b C 26.8940 -16.1936 4 O6a O 23.2571 -16.8978 5 O6a O 24.4732 -14.7912 6 N1a N 28.1045 -16.8919 BOND 5 1 1 2 1 2 1 3 1 3 2 4 1 4 2 5 2 5 3 6 1 ///