2,4-dinitrophenyl-S-glutathione

Three steps

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2 and 7 moreextracellular space, cytosolOne of 5 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLCO1A2, SLCO1B3, AANAT, CPT1A and 2 moreextracellular space, cytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2 and 7 moreextracellular space, cytosolOne of 5 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by SLCO1A2, SLCO1B3, AANAT, CRAT and 1 moreextracellular space, cytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by SLCO1A2, SLCO1B3, AANAT, ACAA1 and 3 moreextracellular space, cytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by SLCO1A2, SLCO1B3, AANAT, CPT1A and 2 moreextracellular space, cytosolOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by SLCO1B1, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, endoplasmic reticulumOne of 7 routes

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 9 moreextracellular space, cytosol

• (11Z,14Z)-eicosadienoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• (17Z)-hexacosenoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• pristanoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. fatty-acid-CoA ligase

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 10 moreextracellular space, cytosol

• undecanoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, ACSM4 and 5 moreextracellular space, cytosolOne of 3 routes

• 16alpha-hydroxyestroneReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. Estrone 3-sulfate sulfohydrolase
  3. unspecific monooxygenase (estrone)

  Catalysed by SLCO1B1, STS, CYP1A1, CYP1A2 and 22 moreextracellular space, cytosolOne of 3 routes

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. (9S)-hydroperoxy-(10E,12Z)-octadecadienoate + 2 glutathione = (9S)-hydroxy-(10E,12Z)-octadecadienoate + glutathione disulfide + H2O

  Catalysed by SLCO1A2, SLCO1B3, ABCC4, GPX1 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• 7R-hydroxy-5S,6S-epoxy-(8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of arachidonate (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 = 7R-hydroxy-5S,6S-epoxy-(8Z,11Z,14Z)-eicosatrienoate

  Catalysed by SLCO1B1, ALOX5, ALOXE3extracellular space, cytosol

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. phosphatidate phosphatase (1-lyso-2-arachidonoyl-phosphatidate)

  Catalysed by SLCO1B1, FAAH, PLPP1, PLPP3 and 9 moreextracellular space, cytosolOne of 4 routes

• 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 10 moreextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-heptadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 9 moreextracellular space, cytosol

• tricosanoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1B1extracellular space, cytosolOne of 12 routes

• 3beta,7alpha-dihydroxyandrost-5-en-17-oneReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. 3beta-hydroxyandrost-5-en-17-one + reduced [NADPH--hemoprotein reductase] + O2 = 3beta,7alpha-dihydroxyandrost-5-en-17-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, STS, CYP7B1extracellular space, cytosol

• cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 10 moreextracellular space, cytosol

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A24extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• glycodeoxycholateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cytochrome P450 (cholate)
  3. Glycodeoxycholate amidohydrolase

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

• (R)-lipoateReach from here →
  1. transport of dopamine (cytosol to extracellular)
  2. dopamine,ascorbate:oxygen oxidoreductase (beta-hydroxylating)
  3. ascorbate to dehydroascorbic acid conversion

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosol

• androst-5-ene-3,17-dioneReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. dehydroepiandrosterone:NAD+ oxidoreductase

  Catalysed by SLCO1B1, STS, HSD3B1, HSD3B2extracellular space, cytosolOne of 3 routes

• pentanalReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. pentanoate(in) + estrone 3-sulfate(out) = pentanoate(out) + estrone 3-sulfate(in)
  3. pentanal + NAD(+) + H2O = pentanoate + NADH + 2 H(+)

  Catalysed by SLCO1B1, SLC22A9, ALDH9A1extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• 1-heptadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. 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(+)
  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 SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. 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(+)
  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 SLCO1B1, ABHD16Aextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2 and 7 moreextracellular space, cytosolOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by SLCO1B1, CRAT, CROTextracellular space, cytosol, endoplasmic reticulum, peroxisomeOne of 5 routes

• (3E)-decenoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by SLCO1A2, SLCO1B3, AANAT, ACADM and 3 moreextracellular space, cytosol, mitochondrial matrix

• 2-glyceryl-prostaglandin G2Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2

  Catalysed by SLCO1B1, FAAH, PTGS2extracellular space, cytosol

• 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-O-(9Z-octadecenyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 9 moreextracellular space, cytosol

• N-tetradecanoylglycineReach from here →
  1. transport of dopamine (cytosol to extracellular)
  2. dopamine + 2 L-ascorbate + O2 = (R)-noradrenaline + 2 monodehydro-L-ascorbate radical + H2O
  3. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLCO1A2, SLCO1B3, DBH, PAMextracellular space, cytosolOne of 2 routes

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, HADHA and 2 moreextracellular space, cytosol, mitochondrial matrix

• N-eicosanoylglycinateReach from here →
  1. transport of leukotriene C4 (cytosol to extracellular)
  2. leukotriene C4 hydrolysis
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by SLCO1B1, BAATextracellular space, cytosol

• N-docosanoylglycineReach from here →
  1. transport of leukotriene C4 (cytosol to extracellular)
  2. leukotriene C4 hydrolysis
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by SLCO1B1, BAATextracellular space, cytosol

• N-hexacosanoylglycineReach from here →
  1. transport of leukotriene C4 (cytosol to extracellular)
  2. leukotriene C4 hydrolysis
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by SLCO1B1, BAATextracellular space, cytosol

• 4-hydroxyestroneReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, STS, CYP1A1, CYP1A2 and 4 moreextracellular space, cytosol

• 6alpha-hydroxyestroneReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 6alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, STS, CYP1A1extracellular space, cytosol

• 15alpha-hydroxyestroneReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 15alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, STS, CYP1A1extracellular space, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2 and 7 moreextracellular space, cytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. transport of serotonin (cytosol to extracellular)
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by SLCO1A2, SLCO1B3, AANAT, SLC27A2 and 7 moreextracellular space, cytosolOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by SLCO1A2, SLCO1B3, ABCC4, PTGES and 5 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by SLCO1A2, SLCO1B3, ABCC4, GPX1 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
  3. (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + NAD(+) = 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoate + NADH + H(+)

  Catalysed by SLCO1B1, PTGS2, HPGDextracellular space, cytosol