serotonin

Three steps

• prostaglandin J2Reach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin J2 hydrolysis

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 2 routes

• 15-oxoprostaglandin F2alphaReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin F2alpha (cytosol to extracellular)
  3. 15-keto-prostaglandin F2alpha reduction

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SULT1B1, SULT1A3 and 2 moreextracellular space, cytosol

• dopamine 4-O-sulfateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. Dopamine 4-O-Sulfotransferase

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A1extracellular space, cytosolOne of 2 routes

• hyocholateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. Chenodeoxycholic acid 6alpha-hydroxylase

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• prostaglandin A2-S-(R)-glutathioneReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, GSTA1 and 1 moreextracellular space, cytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, GSTP1 and 1 moreextracellular space, cytosol

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15extracellular space, cytosol

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15extracellular space, cytosol

• N-(9Z-octadecenoyl)glycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

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

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PM20D1extracellular space, cytosol

• N-octadecanoylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 2 routes

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 25 moreextracellular space, cytosolOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 25 moreextracellular space, cytosolOne of 2 routes

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosol

• chenodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + UDP-alpha-D-glucuronate = chenodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by SLCO1A2, SLCO1B3, UGT2A2, UGT1A3extracellular space, cytosol

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 25 moreextracellular space, cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. transport of GSH and serotonin (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 5 moreextracellular space, cytosol

• 2-hydroxyoctanoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by AANAT, CROT, PHYHcytosol, mitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

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

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

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

• 2-hydroxydodecanoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

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

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

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

• 11-cis-retinyl tetradecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

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

• 13-cis-retinyl tetradecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

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

• all-trans-retinyl tetradecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

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

• tetradecyl tetradecanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

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

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach 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 + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

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

• beta-D-glucosyl-(1->3)-O-chenodeoxycholateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, GBA2extracellular space, cytosolOne of 2 routes

• N-hexadecanoylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

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

• N-dodecanoylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• N-decanoylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

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

• N-octanoylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by AANAT, CROT, GLYATL2cytosol, mitochondrial matrixOne of 2 routes

• L-homocarnosineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of Ca2+ and K+ (cytosol to extracellular)
  3. Transport of Homocarnosine

  Catalysed by SLC6A4, SLC24A1, SLC24A5, SLC24A4 and 2 moreextracellular space, cytosolOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

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

• L-cystine-bis-glycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

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

• an N-octadecanoyl-sphingoid baseReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

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

• glycyldehydrophenylalanineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

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

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, FAAH and 1 moreextracellular space, cytosol

• an N-(fatty acyl)-glycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrix

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

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

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• cholesteryl (7Z)-octadecenoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by AANAT, CPT1A, CPT1C, CPT1B and 1 morecytosol

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of prostaglandin G2 (cytosol to extracellular)
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

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

• pyruvateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by AANAT, AGXT2cytosol, mitochondrial matrixOne of 20 routes

• 4a-hydroxytetrahydrobiopterinReach 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, TPH2cytosol

• CHEBI:15467Reach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Acetoacetate:CoA ligase (AMP-forming)
  3. 3-hydroxy-3-methylglutaryl-CoA synthase (acetoacetyl-CoA)

  Catalysed by AANAT, AACS, HMGCS1cytosolOne of 3 routes