CHEBI:16856

Three steps

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + ATP + CoA = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by CYP2C9, ACSL4, ACSL3, ACSL5extracellular space, cytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoyl-CoAReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. unspecific monooxygenase (arachidonate)
  3. 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate + ATP + CoA = 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 27 moreextracellular space, cytosol

• 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. unspecific monooxygenase (arachidonate)
  3. 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate + ATP + CoA = 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 moreextracellular space, cytosol

• cholesterol sulfateReach from here →
  1. transport of GSH and sulfoglycolithocholate (cytosol to extracellular)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. Steryl-Sulfatase

  Catalysed by SLCO1A2, SLCO1B3, STSextracellular space, cytosol, Golgi apparatusOne of 2 routes

• deoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cytochrome P450 (cholate)
  3. deoxycholate + UDP-alpha-D-glucuronate = deoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by SLCO1A2, SLCO1B3, CYP7A1, UGT2A1 and 2 moreextracellular space, cytosol

• hyodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. transport of GSH and lithocholate (cytosol to extracellular)
  2. cytochrome P450 (lithocholate)
  3. hyodeoxycholate + UDP-alpha-D-glucuronate = hyodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4, UGT2A1 and 1 moreextracellular space, cytosol

• hyodeoxycholate 6-O-(beta-D-glucuronate)Reach from here →
  1. transport of GSH and lithocholate (cytosol to extracellular)
  2. cytochrome P450 (lithocholate)
  3. hyodeoxycholate + UDP-alpha-D-glucuronate = hyodeoxycholate 6-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4, UGT2A2 and 2 moreextracellular space, cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. transport of GSH and sulfoglycolithocholate (cytosol to extracellular)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. steroid sulfatase (5-alpha-dihydrotestosterone)

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

• acetoacetateReach from here →
  1. transport of acetylcholine and GSH (cytosol to extracellular)
  2. Acetylcholine aectylhydrolase
  3. transport of acetate and acetoacetate (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHE and 5 moreextracellular space, cytosolOne of 10 routes

• 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerolReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerol

  Catalysed by FAAH, ALOX15Bextracellular space, cytosol

• (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate = (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate

  Catalysed by ALOX15B, ALOX15, ALOX12, CYP2J2extracellular space, cytosol

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + glutathione = (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 8 morecytosol

• (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by ALOX5, ALOX15Bextracellular space, cytosol

• a phenyl acetateReach from here →
  1. transport of acetylcholine and GSH (cytosol to extracellular)
  2. Acetylcholine aectylhydrolase
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHE and 3 moreextracellular space, cytosol

• an aryl sulfateReach from here →
  1. transport of GSH and sulfoglycolithocholate (cytosol to extracellular)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, STS, ARSL and 5 moreextracellular space, cytosol

• 3-sulfinopyruvateReach from here →
  1. cystine to cysteine conversion
  2. L-Cysteine:oxygen oxidoreductase
  3. 3-sulfino-L-alanine:2-oxoglutarate aminotransferase

  Catalysed by CDO1, GOT1cytosolOne of 2 routes

• S-methyl glutathioneReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. apo-[alkylcobalamin reductase] + methylcob(III)alamin + glutathione = S-methyl glutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 7 morecytosol

• N-hexadecanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL3cytosol

• N-dodecanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosolOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoylglycineReach from here →
  1. transport of dopamine and GSH (cytosol to extracellular)
  2. dopamine + 2 L-ascorbate + O2 = (R)-noradrenaline + 2 monodehydro-L-ascorbate radical + H2O
  3. N-(9Z,12Z,15Z)-octadecatrienoylglycine + 2 L-ascorbate + O2 = N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLCO1A2, SLCO1B3, DBH, PAMextracellular space, cytosol

• N-decanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosolOne of 2 routes

• N-octanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosolOne of 2 routes

• D-histidineReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and ornithine (cytosol to extracellular)
  3. D-histidine(in) + L-ornithine(out) + H(+)(in) = D-histidine(out) + L-ornithine(in) + H(+)(out)

  Catalysed by SLC7A6, SLC25A2cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-homoarginineReach from here →
  1. cystine to cysteine conversion
  2. transport of arginine and cysteine (cytosol to extracellular)
  3. L-homoarginine(in) + L-arginine(out) = L-homoarginine(out) + L-arginine(in)

  Catalysed by SLC7A6, SLC25A29cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-homocarnosineReach from here →
  1. transport of GSH and histamine (cytosol to extracellular)
  2. L-histidine + H(+) = histamine + CO2
  3. 4-aminobutanoate + L-histidine + ATP = L-homocarnosine + ADP + phosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, HDC, CARNS1extracellular space, cytosolOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

  Catalysed by LTC4S, GARTcytosol

• N(2)-[4-(indol-3-yl)butanoyl]-L-glutamineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. S-Adenosyl-L-methionine:phenylethanolamine N-methyltransferase
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, PNMT, COMT and 1 moreextracellular space, cytosol

• indoxyl sulfateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  3. indoxyl sulfate(out) + a dicarboxylate(in) = indoxyl sulfate(in) + a dicarboxylate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A6, SLC22A8extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• glycyldehydrophenylalanineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by LTC4S, DPEP1cytosol

• S-adenosylglutathioneReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. apo-[alkylcobalamin reductase] + adenosylcob(III)alamin + glutathione = S-adenosylglutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 7 morecytosol

• 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerolReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerol

  Catalysed by FAAH, ALOX15Bextracellular space, cytosol

• 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidineReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and glutamine (cytosol to extracellular)
  3. N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + L-glutamine + ATP + H2O = 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine + L-glutamate + ADP + phosphate + H(+)

  Catalysed by SLC3A2, SLC7A5, SLC7A10, PFAScytosol, extracellular space

• kinetensinReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. Chymase

  Catalysed by SLC7A5, CMA1cytosol, extracellular spaceOne of 3 routes

• an N-(fatty acyl)-glycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosol

• 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreextracellular space, cytosol

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosol

• (7Z)-octadecenoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosolOne of 3 routes

• acetaldehydeReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and threonine (cytosol to extracellular)
  3. L-threonine acetaldehyde-lyase (glycine-forming)

  Catalysed by SLC7A5cytosol, extracellular space

• CHEBI:15345Reach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 30 moreextracellular space, cytosolOne of 2 routes

• acetylpyruvateReach from here →
  1. transport of acetylcholine and GSH (cytosol to extracellular)
  2. Acetylcholine aectylhydrolase
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHE and 1 moreextracellular space, cytosolOne of 2 routes

• all-trans-retinoic acidReach from here →
  1. transport of acetylcholine and GSH (cytosol to extracellular)
  2. Acetylcholine aectylhydrolase
  3. transport of acetate and retinoate (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHE and 3 moreextracellular space, cytosolOne of 8 routes

• 4a-hydroxytetrahydrobiopterinReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and tryptophan (cytosol to extracellular)
  3. L-tryptophan,tetrahydrobiopterin:oxygen oxidoreductase(5-hydroxylating)

  Catalysed by SLC7A5, TPH1, TPH2cytosol, extracellular spaceOne of 3 routes

• CHEBI:15380Reach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 31 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. Production of Tiglylcarnitine

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 31 moreextracellular space, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 30 moreextracellular space, cytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• palmitoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 37 moreextracellular space, cytosolOne of 11 routes

• oleoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosolOne of 11 routes