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indole metabolism

see figure Biochemistry: - indole metabolism 1 - enzyme: aromatic amino acid decarboxylase - substrate: tryptophan - product: tryptamine + CO2 - indole metabolism 2 - enzyme: monoamine oxidase - substrate: tryptamine + NADH + H2O + O2 - product: tryptophal + NAD + NH3 + H2O2 - indole metabolism 3 - enzyme: aldehyde oxidoreductase - substrate: tryptophal - product: tryptophol - indole metabolism 4 - enzyme: aldehyde oxidoreductase - substrate: tryptophal - product: indoleacetic acid - indole metabolism 5 - enzyme: aminotransferase - substrate: tryptophan - product: indolepyruvate - indole metabolism 6 - enzyme: carboxy-lyase - substrate: indolepyruvate - product: indoleacetic acid + CO2 - indole metabolism 7 - enzyme: tryptophan hydroxylase - substrate: tryptophan + O2 + NADPH - product: 5-OH tryptophan + H2O + NADP - indole metabolism 8 - enzyme: 5-OH tryptophan decarboxylase - substrate: 5-OH tryptophan - product: serotonin + CO2 - indole metabolism 9 - enzyme: monoamine oxidase - substrate: serotonin + NADH + H2O + O2 - product: 5-OH tryptophal + NAD + NH3 + H2O2 - indole metabolism 10 - enzyme: aldehyde oxidoreductase - substrate: 5-OH tryptophal - product: 5-OH indoleacetic acid - indole metabolism 11 - enzyme: alcohol oxidoreductase - substrate: 5-OH tryptophal - product: 5-OH tryptophol - indole metabolism 12 - enzyme: N-methyltransferase - substrate: serotonin - product: N'methylserotonin - indole metabolism 13 - enzyme: acetyltransferase - substrate: serotonin - product: N'acetylserotonin - indole metabolism 14 - enzyme: aminotransferase - substrate: 5-OH tryptophan - product: 5-OH indolepyruvate - indole metabolism 15 - enzyme: carboxy-lyase - substrate: 5-OH indolepyruvate - product: 5-OH indoleacetic acid

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indole

General

biosynthetic pathway or anabolic pathway tryptophan metabolism

Properties

EVENTS: enzymatic reaction ENZYME: aromatic amino-acid decarboxylase MOTIF: active site SUBSTRATE: tryptophan PRODUCT: tryptamine CO2 TAG: INDOLE-METABOLISM-1 enzymatic reaction ENZYME: monoamine oxidase COMPARTMENT: mitochondrial outer membrane (GO:0005741) MOTIF: membrane region active site metal ion-binding site SUBSTRATE: tryptamine NADH H2O O2 PRODUCT: tryptophal NAD NH3 hydrogen peroxide TAG: INDOLE-METABOLISM-2 enzymatic reaction ENZYME: aldehyde oxidoreductase MOTIF: active site SUBSTRATE: tryptophal PRODUCT: tryptophol TAG: INDOLE-METABOLISM-3 enzymatic reaction ENZYME: aldehyde oxidoreductase MOTIF: active site SUBSTRATE: tryptophal PRODUCT: indoleacetic acid TAG: INDOLE-METABOLISM-4 enzymatic reaction ENZYME: aminotransferase MOTIF: cofactor-binding site COFACTOR-BOUND: pyridoxal phosphate SUBSTRATE: tryptophan PRODUCT: indolepyruvate TAG: INDOLE-METABOLISM-5 enzymatic reaction ENZYME: carboxy-lyase MOTIF: active site SUBSTRATE: indolepyruvate PRODUCT: indoleacetic acid CO2 TAG: INDOLE-METABOLISM-6 enzymatic reaction ENZYME: tryptophan hydroxylase MOTIF: ACT {18-92} MOTIF: Ser phosphorylation site {S58} cofactor-binding site COFACTOR-BOUND: 5,6,7-8-tetrahydrobiopterin Iron [Fe]-binding site SITE: 272-272 Iron [Fe]-binding site SITE: 277-277 Iron [Fe]-binding site SITE: 317-317 cofactor-binding site FOR-BINDING-OF: NADPH SUBSTRATE: tryptophan O2 NADPH PRODUCT: 5-hydroxytryptophan H2O NADP TAG: INDOLE-METABOLISM-7 enzymatic reaction ENZYME: dopa decarboxylase MOTIF: active site MOTIF: cofactor-binding site COFACTOR-BOUND: pyridoxal phosphate BOUND-VIA: lysine residue lysine residue SUBSTRATE: 5-hydroxytryptophan PRODUCT: serotonin CO2 TAG: INDOLE-METABOLISM-8 enzymatic reaction ENZYME: monoamine oxidase COMPARTMENT: mitochondrial outer membrane (GO:0005741) MOTIF: membrane region active site metal ion-binding site SUBSTRATE: serotonin NADH H2O O2 PRODUCT: 5-OH tryptophal NAD NH3 hydrogen peroxide TAG: INDOLE-METABOLISM-9 enzymatic reaction ENZYME: aldehyde oxidoreductase MOTIF: active site SUBSTRATE: 5-OH tryptophal PRODUCT: 5-OH indoleacetic acid TAG: INDOLE-METABOLISM-10 enzymatic reaction ENZYME: alcohol oxidoreductase MOTIF: active site SUBSTRATE: 5-OH tryptophal PRODUCT: 5-OH tryptophol TAG: INDOLE-METABOLISM-11 enzymatic reaction ENZYME: N-methyltransferase MOTIF: active site SUBSTRATE: serotonin PRODUCT: N'methyl-serotonin TAG: INDOLE-METABOLISM-12 enzymatic reaction ENZYME: acetyl transferase MOTIF: active site SUBSTRATE: serotonin PRODUCT: N'acetyl-serotonin TAG: INDOLE-METABOLISM-13 enzymatic reaction ENZYME: aminotransferase MOTIF: cofactor-binding site COFACTOR-BOUND: pyridoxal phosphate SUBSTRATE: 5-hydroxytryptophan PRODUCT: 5-OH indole pyruvate TAG: INDOLE-METABOLISM-14 enzymatic reaction ENZYME: carboxy-lyase MOTIF: active site SUBSTRATE: 5-OH indole pyruvate PRODUCT: 5-OH indoleacetic acid TAG: INDOLE-METABOLISM-15

References

  1. Principles of Biochemistry 6th ed., White, Handler, Smith, Hill, & Lehman (eds.) McGraw-Hill, NY 1978, pg 722