serotonin

Three steps

• (15S)-hydroperoxy-(5Z,8Z,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 + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15B and 2 moreextracellular space, cytosol

• (5S)-hydroperoxy-(6E,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 + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX5extracellular space, cytosol

• 7,8-dihydrofolateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)

  Catalysed by AANAT, BAAT, MTO1cytosol

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 2 morecytosol, mitochondrial matrix

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of aspartate (cytosol to extracellular)
  3. L-Citrulline:L-aspartate ligase (AMP-forming)

  Catalysed by SLC6A4, SLC1A7, SLC1A3, SLC1A2 and 3 moreextracellular space, cytosolOne of 2 routes

• propane-1,3-diamineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. [eIF5A protein]-L-lysine + spermidine = [eIF5A protein]-deoxyhypusine + propane-1,3-diamine

  Catalysed by AANAT, SAT1, SAT2, DHPScytosol

• L-dopaReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. L-dopa + H(+) = dopamine + CO2

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

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• a 1-acylglycerone 3-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 2 morecytosol, Golgi apparatus

• N(6)-(1,2-dicarboxyethyl)-AMPReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of aspartate (cytosol to extracellular)
  3. IMP:L-aspartate ligase (GDP-forming)

  Catalysed by SLC6A4, SLC1A7, SLC1A3, SLC1A2 and 4 moreextracellular space, cytosolOne of 2 routes

• O-acetyl-(R)-carnitineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by AANAT, CPT1A, CPT1C, CPT1BcytosolOne of 9 routes

• L-histidineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. L-histidine + H(+) = histamine + CO2

  Catalysed by SLCO1A2, SLCO1B3, HDCextracellular space, cytosol

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 2 morecytosol, Golgi apparatusOne of 2 routes

• an N-acylglycineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 4 morecytosol, Golgi apparatusOne of 2 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by AANAT, NAGS, GOT2, GOT1cytosol, mitochondrial matrixOne of 3 routes

• guanidinoacetateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-Arginine:glycine amidinotransferase

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 3 morecytosol, Golgi apparatus

• glutathioneReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ABCC4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 17 routes

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

  Catalysed by AANAT, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-kynurenineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by AANAT, KYNUcytosol, mitochondrial matrix

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

  Catalysed by AANAT, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 7 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sn-glycerol 3-phosphate + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 5 morecytosol, Golgi apparatus

• taurocyamineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by AANAT, BAAT, GATMcytosol

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of aspartate (cytosol to extracellular)
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by SLC6A4, SLC1A7, SLC1A3, SLC1A2 and 3 moreextracellular space, cytosol

• L-cysteateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. L-cysteate + H(+) = taurine + CO2

  Catalysed by AANAT, BAAT, GADL1, CSADcytosol

• L-phenylalanineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and phenylalanine (cytosol to extracellular)

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 38 routes

• N(1)-acetylspermineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

  Catalysed by AANAT, SAT1, SAT2, PAOXcytosol

• 3-hydroxy-L-kynurenineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by AANAT, KYNUcytosol, mitochondrial matrix

• gamma-L-glutamyl-L-cysteineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by AANAT, NAGS, GCLC, GCLMcytosol, mitochondrial matrixOne of 2 routes

• L-homocysteineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  3. L-homocysteine + L-serine = L,L-cystathionine + H2O

  Catalysed by AANAT, NAGS, CBScytosol, mitochondrial matrixOne of 2 routes

• S-methyl-L-methionineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by AANAT, NAGS, BHMT2cytosol, mitochondrial matrix

• 3-oxosphinganineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

  Catalysed by AANAT, SLC27A2, ACSL4, ACSL3 and 8 morecytosol

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

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

• L-tyrosineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by AANAT, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrixOne of 4 routes

• N(1)-acetylspermidineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine + acetyl-CoA = N(1)-acetylspermidine + CoA + H(+)

  Catalysed by AANAT, SAT1, SAT2cytosol

• 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 3 routes

• 3-aminopropanalReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

  Catalysed by AANAT, SAT1, SAT2, SMOXcytosol

• trans-4-hydroxy-L-prolineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by AANAT, SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• (2S)-2-[5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of aspartate (cytosol to extracellular)
  3. 1-(5-Phosphoribosyl)-5-amino-4-carboxyimidazole:L-aspartate ligase (ADP-forming)

  Catalysed by SLC6A4, SLC1A7, SLC1A3, SLC1A2 and 3 moreextracellular space, cytosolOne of 2 routes

• N(8)-acetylspermidineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by AANAT, SAT1, SAT2cytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by AANATcytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase

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

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

  Catalysed by AANAT, NAGS, CARS2cytosol, mitochondrial matrix

• N(tau)-methylhistamineReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:histamine N-tele-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, HNMTextracellular space, cytosolOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by AANAT, ASAH1, ACER2, ACER1 and 14 morecytosol, Golgi apparatus

• N-formyl-L-kynurenineReach 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 + O2 = N-formyl-L-kynurenine

  Catalysed by DDC, TPH1, TPH2, IDO1 and 2 more

• (3S)-citramalyl-CoAReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

  Catalysed by AANAT, SUCLG1, SUCLG2, SUCLA2 and 1 morecytosol, mitochondrial matrix

• phosphoenolpyruvateReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by AANAT, ACLY, PCK1, PCK2cytosol

• L-methionine (S)-S-oxideReach from here →
  1. acetyl-CoA:aralkylamine N-acetyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by AANAT, NAGS, MSRAcytosol, mitochondrial matrix