acetylcholine

Three steps

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 5 routes

• 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. Acetylcholine aectylhydrolase
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-O-acyl-N-(acetyl)-sphing-4-enine

  Catalysed by BCHE, ACHE, ASAH1, PLA2G15cytosol

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by BCHE, ACHE, CHAT, CPT1A and 2 morecytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 5 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP1A1, CYP1A2 and 3 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1B3, SLCO1B1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by BCHE, ACHE, CHAT, CRAT and 1 morecytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by BCHE, ACHE, CHAT, ACAA1 and 3 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by BCHE, ACHE, CHAT, CPT1A and 2 morecytosolOne of 2 routes

• pristanoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. fatty-acid-CoA ligase

  Catalysed by BCHE, ACHE, CHAT, SLC27A2cytosolOne of 2 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. Acetylcholine aectylhydrolase
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine

  Catalysed by BCHE, ACHE, ASAH1, PLA2G15cytosol

• undecanoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by BCHE, ACHE, CHAT, ACSM4 and 5 morecytosolOne of 3 routes

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9S)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS1 and 1 morecytosol

• (9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9R)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS1 and 1 morecytosol

• 7-oxolithocholateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + NAD(+) = 7-oxolithocholate + NADH + H(+)

  Catalysed by SLCO1B3, SLCO1A2, HSD17B10extracellular space, cytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosolOne of 3 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosolOne of 3 routes

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

  Catalysed by SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by SLCO1B3, SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by BCHE, ACHE, CHDH, MOCOScytosolOne of 2 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B3, SLCO1B1, CYP1A1, CYP1A2 and 25 moreextracellular space, cytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B3, SLCO1B1, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. Acetylcholine aectylhydrolase
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phosphoserine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by BCHE, ACHE, ASAH1, PLA2G15cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. Acetylcholine aectylhydrolase
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by BCHE, ACHE, ASAH1, PLA2G15cytosolOne of 8 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by BCHE, ACHE, CHAT, ACADM and 3 morecytosol, mitochondrial matrix

• 2-glyceryl-prostaglandin H2Reach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• 11beta-prostaglandin F2Reach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1B3, SLCO1B1, AKR1C3, AKR1C2extracellular space, cytosol

• N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
  1. Acetylcholine aectylhydrolase
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by BCHE, ACHE, ASAH1, CERKcytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by BCHE, ACHE, CHAT, HADHA and 2 morecytosol, mitochondrial matrix

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP3A7extracellular space, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. Acetylcholine aectylhydrolase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by BCHE, ACHE, CHAT, SLC27A2 and 7 morecytosolOne of 4 routes

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by SLCO1B3, SLCO1B1, TBXAS1, CYP2S1 and 1 moreextracellular space, cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol

• prostaglandin H1Reach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosolOne of 3 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. transport of acetylcholine (cytosol to extracellular)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. Acetylcholine aectylhydrolase
  2. choline + A = betaine aldehyde + AH2
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by BCHE, ACHE, CHDH, PTGS2cytosol