serotonin

Three steps

• (R)-normetanephrineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, COMT, LRTOMTextracellular space, cytosol

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

• ophthalmateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrix

• S-methylmercury-L-cysteineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by AANAT, NAGS, SLC7A8cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-aminoisobutanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by AANAT, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 11-cis-retinyl esterReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol + a fatty acyl-CoA = 11-cis-retinyl ester + CoA

  Catalysed by AANAT, DGAT1, LRAT, AWAT1 and 2 morecytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by AANAT, ACLY, AGXT2cytosol

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrixOne of 2 routes

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by AANAT, ACSM4, ACSM1, ACSM2A and 5 morecytosol

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by AANAT, CROT, MOGAT2, MOGAT1cytosol, mitochondrial matrix

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 7 morecytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrixOne of 3 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by AANAT, ACSM4, ACSM1, ACSM2A and 4 morecytosol

• S-disulfanyl-L-cysteineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by AANAT, NAGS, CARS2cytosol, mitochondrial matrix

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, UGT1A9 and 5 moreextracellular space, cytosol

• 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5
  3. 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, UGT2B7 and 2 moreextracellular space, cytosol

• 15-O-(beta-D-glucuronosyl)-prostaglandin B1Reach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin B1 (cytosol to extracellular)
  3. prostaglandin B1 + UDP-alpha-D-glucuronate = 15-O-(beta-D-glucuronosyl)-prostaglandin B1 + UDP + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, UGT1A9 and 3 moreextracellular space, cytosol

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

  Catalysed by AANAT, CPT1A, CPT1C, CPT1B and 7 morecytosol

• (R)-noradrenaline 4'-O-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. sulfotransferase (noradrenaline)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3extracellular space, cytosolOne of 2 routes

• L-homocysteine thiolactoneReach from here →
  1. transport of GSH and serotonin (cytosol to extracellular)
  2. Formation of Homocystine
  3. arylesterase (homocysteine-thiolactone)

  Catalysed by SLCO1A2, SLCO1B3, PON1, PON2 and 1 moreextracellular space, cytosol

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 8 morecytosolOne of 2 routes

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by AANAT, HADHA, ACADVL, HADHB and 2 morecytosol, mitochondrial matrix

• (2E,4Z,7Z,10Z,13Z)-hexadecapentaenoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
  3. Fatty Acid Beta Oxidation (C16:4->C16:5), Mitochondrial

  Catalysed by AANAT, HADHA, ACADVL, HADHBcytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial
  3. (7Z,10Z,13Z)-hexadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by AANAT, HADHA, ACADVL, HADHB and 2 morecytosol, mitochondrial matrix

• (2E,4Z,7Z)-decatrienoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial
  3. Fatty Acid Beta Oxidation (C10:2->C10:3), Mitochondrial

  Catalysed by AANAT, ECHS1, ACAA2, HADH and 1 morecytosol, mitochondrial matrixOne of 3 routes

• ursodeoxycholate 3-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. ursodeoxycholate + 3'-phosphoadenylyl sulfate = ursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• tauroursodeoxycholate 3-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. tauroursodeoxycholate + 3'-phosphoadenylyl sulfate = tauroursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• glycoursodeoxycholate 3-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of glycoursodeoxycholate (cytosol to extracellular)
  3. glycoursodeoxycholate + 3'-phosphoadenylyl sulfate = glycoursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• chenodeoxycholate 3-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + 3'-phosphoadenylyl sulfate = chenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• deoxycholateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cytochrome P450 (cholate)

  Catalysed by SLCO1A2, SLCO1B3, CYP7A1extracellular space, cytosolOne of 4 routes

• docosanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. Docosanoyl-CoA hydrolase

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 7 morecytosolOne of 4 routes

• CHEBI:240943Reach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrixOne of 4 routes

• hypochlorous acidReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of chloride (cytosol to extracellular)
  3. Peroxidase

  Catalysed by SLC6A4, SLC12A2, SLC12A1, LPOextracellular space, cytosolOne of 4 routes

• octadecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Stearoyl-CoA hydrolase

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 9 morecytosolOne of 4 routes

• octanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. Octanoyl-CoA hydrolase

  Catalysed by AANAT, CROT, ACOT7cytosol, mitochondrial matrixOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. fatty acylamide amidohydrolase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, FAAHextracellular space, cytosol

• imidazole-4-acetaldehydeReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. amine oxidase copper containing (histamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 1 moreextracellular space, cytosolOne of 2 routes

• alpha-linolenic acidReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by AANAT, CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 2 routes

• phenylacetylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrixOne of 6 routes

• decanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. Decanoyl-CoA hydrolase

  Catalysed by AANAT, ACSM4, ACSM1, ACSM2A and 4 morecytosolOne of 2 routes

• 3,4-dihydroxyphenylacetaldehydeReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. monoamine oxidase (dopamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 3 moreextracellular space, cytosolOne of 2 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 7 morecytosolOne of 2 routes

• 5-hydroxytryptophanReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
  3. L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)

  Catalysed by DDC, TPH1, TPH2cytosolOne of 2 routes

• hexacosan-1-olReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + 2 NADPH + 2 H(+) = hexacosan-1-ol + 2 NADP(+) + CoA

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, STSextracellular space, cytosolOne of 3 routes

• O-decanoyl-(R)-carnitineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + (R)-carnitine = O-decanoyl-(R)-carnitine + CoA

  Catalysed by AANAT, ACSM4, ACSM1, ACSM2A and 5 morecytosol

• pyridoxine 5'-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by AANAT, SCLYcytosol, mitochondrial matrix

• CHEBI:28918Reach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:phenylethanolamine N-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, PNMTextracellular space, cytosol

• N-acetyl-L-cysteineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by AANAT, NAGScytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A6extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 6 routes