ENTRY R04901 Reaction NAME (2S)-flavan-4-ol:NADP+ 4-oxidoreductase; cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase DEFINITION Luteoforol + NADP+ <=> Eriodictyol + NADPH + H+ EQUATION C05907 + C00006 <=> C05631 + C00005 + C00080 COMMENT flavanone 4-reductase dihydroflavonol 4-reductase RCLASS RC00001 C00005_C00006 RC00234 C05631_C05907 ENZYME 1.1.1.234 PATHWAY rn00941 Flavonoid biosynthesis 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 1.1.1.234 R04901 Luteoforol + NADP+ <=> Eriodictyol + NADPH + H+ IUBMB reaction hierarchy [BR:br08202] 1. Oxidoreductase reactions 1.1.1.234 R03827 (2S)-Flavan-4-ol <=> (2S)-Flavanone R04901 Luteoforol <=> Eriodictyol ORTHOLOGY K13082 bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase [EC:1.1.1.219 1.1.1.234] /// ENTRY R04902 Reaction NAME eriodictyol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase DEFINITION Eriodictyol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Pentahydroxyflavanone + [Oxidized NADPH---hemoprotein reductase] + H2O EQUATION C05631 + C03024 + C00007 <=> C05911 + C03161 + C00001 COMMENT flavonoid 3',5'-hydroxylase flavonoid 3',5'-monooxygenase second step of two-step reaction (see R02443, R02442+R04902) RCLASS RC00046 C05631_C05911 ENZYME 1.14.14.81 PATHWAY rn00941 Flavonoid 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 1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor 1.14.14.81 R04902 Eriodictyol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Pentahydroxyflavanone + [Oxidized NADPH---hemoprotein reductase] + H2O IUBMB reaction hierarchy [BR:br08202] 1. Oxidoreductase reactions 1.14.14.81 R07370 3'-Hydroxyflavanone <=> 3',5'-Dihydroxyflavanone R04902 Eriodictyol <=> Pentahydroxyflavanone ORTHOLOGY K13083 flavonoid 3',5'-hydroxylase [EC:1.14.14.81] DBLINKS RHEA: 61103 /// ENTRY R04903 Reaction NAME 5-hydroxyindoleacetaldehyde:NAD+ oxidoreductase DEFINITION 5-Hydroxyindoleacetaldehyde + NAD+ + H2O <=> 5-Hydroxyindoleacetate + H+ + NADH EQUATION C05634 + C00003 + C00001 <=> C05635 + C00080 + C00004 RCLASS RC00001 C00003_C00004 RC00080 C05634_C05635 ENZYME 1.2.1.3 PATHWAY rn00380 Tryptophan metabolism rn01100 Metabolic pathways BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.2 Acting on the aldehyde or oxo group of donors 1.2.1 With NAD+ or NADP+ as acceptor 1.2.1.3 R04903 5-Hydroxyindoleacetaldehyde + NAD+ + H2O <=> 5-Hydroxyindoleacetate + H+ + NADH IUBMB reaction hierarchy [BR:br08202] 1. Oxidoreductase reactions 1.2.1.3 R00538 Aldehyde <=> Carboxylate R04903 5-Hydroxyindoleacetaldehyde <=> 5-Hydroxyindoleacetate ORTHOLOGY K00128 aldehyde dehydrogenase (NAD+) [EC:1.2.1.3] K00149 aldehyde dehydrogenase family 9 member A1 [EC:1.2.1.47 1.2.1.3] K14085 aldehyde dehydrogenase family 7 member A1 [EC:1.2.1.31 1.2.1.8 1.2.1.3] DBLINKS RHEA: 31218 /// ENTRY R04904 Reaction NAME 5-hydroxyindoleacetaldehyde:oxygen oxidoreductase DEFINITION 5-Hydroxyindoleacetaldehyde + Oxygen + H2O <=> 5-Hydroxyindoleacetate + Hydrogen peroxide EQUATION C05634 + C00007 + C00001 <=> C05635 + C00027 RCLASS RC00080 C05634_C05635 RC02755 C00007_C00027 ENZYME 1.2.3.1 PATHWAY rn00380 Tryptophan metabolism rn01100 Metabolic pathways BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.2 Acting on the aldehyde or oxo group of donors 1.2.3 With oxygen as acceptor 1.2.3.1 R04904 5-Hydroxyindoleacetaldehyde + Oxygen + H2O <=> 5-Hydroxyindoleacetate + Hydrogen peroxide IUBMB reaction hierarchy [BR:br08202] 1. Oxidoreductase reactions 1.2.3.1 R00635 Aldehyde <=> Carboxylate R04904 5-Hydroxyindoleacetaldehyde <=> 5-Hydroxyindoleacetate ORTHOLOGY K00157 aldehyde oxidase [EC:1.2.3.1] /// ENTRY R04905 Reaction NAME S-adenosyl-L-methionine:N-acetylserotonin O-methyltransferase DEFINITION S-Adenosyl-L-methionine + 5-Hydroxyindoleacetate <=> S-Adenosyl-L-homocysteine + 5-Methoxyindoleacetate EQUATION C00019 + C05635 <=> C00021 + C05660 RCLASS RC00003 C00019_C00021 RC00392 C05635_C05660 ENZYME 2.1.1.4 PATHWAY rn00380 Tryptophan metabolism BRITE Enzymatic reactions [BR:br08201] 2. Transferase reactions 2.1 Transferring one-carbon groups 2.1.1 Methyltransferases 2.1.1.4 R04905 S-Adenosyl-L-methionine + 5-Hydroxyindoleacetate <=> S-Adenosyl-L-homocysteine + 5-Methoxyindoleacetate ORTHOLOGY K00543 acetylserotonin O-methyltransferase [EC:2.1.1.4] /// ENTRY R04906 Reaction DEFINITION 5-Hydroxyindoleacetate <=> 5-Hydroxyindoleacetylglycine EQUATION C05635 <=> C05832 COMMENT incomplete reaction RCLASS RC00090 C05635_C05832 ENZYME 6.3.2.- PATHWAY rn00380 Tryptophan metabolism BRITE Enzymatic reactions [BR:br08201] 6. Ligase reactions 6.3 Forming carbon-nitrogen bonds 6.3.2 Acid-D-amino-acid ligases (peptide synthases) 6.3.2.- R04906 5-Hydroxyindoleacetate <=> 5-Hydroxyindoleacetylglycine /// ENTRY R04907 Reaction NAME 3-hydroxykynurenamine:oxygen oxidoreductase(deaminating)(flavin-containing) DEFINITION 3-Hydroxykynurenamine + Oxygen <=> 4,8-Dihydroxyquinoline + Ammonia + Hydrogen peroxide EQUATION C05636 + C00007 <=> C05637 + C00014 + C00027 COMMENT possibly intermediate RCLASS RC02713 C05636_C05637 RC02755 C00007_C00027 ENZYME 1.4.3.4 PATHWAY rn00380 Tryptophan metabolism BRITE Enzymatic reactions [BR:br08201] 1. Oxidoreductase reactions 1.4 Acting on the CH-NH2 group of donors 1.4.3 With oxygen as acceptor 1.4.3.4 R04907 3-Hydroxykynurenamine + Oxygen <=> 4,8-Dihydroxyquinoline + Ammonia + Hydrogen peroxide ORTHOLOGY K00274 monoamine oxidase [EC:1.4.3.4] /// ENTRY R12370 Reaction NAME 4alpha-formyl-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-3beta-ol,ferrocytochrome-b5:oxygen oxidoreductase DEFINITION 4alpha-Formyl-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-3beta-ol + 2 Ferrocytochrome b5 + Oxygen + 2 H+ <=> 3beta-Hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate + 2 Ferricytochrome b5 + H2O EQUATION C22115 + 2 C00999 + C00007 + 2 C00080 <=> C22116 + 2 C00996 + C00001 COMMENT the last step of three-step reaction (see R12377, R12368+R12369+R12370) RCLASS RC01563 C22115_C22116 ENZYME 1.14.18.10 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 1.14.18.10 R12370 4alpha-Formyl-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-3beta-ol + 2 Ferrocytochrome b5 + Oxygen + 2 H+ <=> 3beta-Hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate + 2 Ferricytochrome b5 + H2O /// ENTRY R12371 Reaction NAME 3beta-hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate:NAD+ 3-oxidoreductase (decarboxylating) DEFINITION 3beta-Hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate + NAD+ <=> Cycloeucalenone + NADH + CO2 + H+ EQUATION C22116 + C00003 <=> C22121 + C00004 + C00011 + C00080 RCLASS RC01163 C22116_C22121 ENZYME 1.1.1.418 PATHWAY rn00100 Steroid biosynthesis rn01100 Metabolic pathways rn01110 Biosynthesis of secondary metabolites MODULE M00917 Phytosterol biosynthesis, squalene 2,3-epoxide => campesterol/sitosterol 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 1.1.1.418 R12371 3beta-Hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate + NAD+ <=> Cycloeucalenone + NADH + CO2 + H+ IUBMB reaction hierarchy [BR:br08202] 1. Oxidoreductase reactions 1.1.1.418 R12366 3beta-Hydroxysteroid-4alpha-carboxylate <=> 3-Oxosteroid R12371 3beta-Hydroxy-4beta,14alpha-dimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-4alpha-carboxylate <=> Cycloeucalenone ORTHOLOGY K23558 plant 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase [EC:1.1.1.418] /// 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 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 ///