glycolithocholic acid

Three steps

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by SLCO1A2, SLCO1B3, UGT1A9, UGT2B7 and 4 moreextracellular space, cytosol

• 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.2
  3. 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, UGT2B7 and 2 moreextracellular space, cytosol

• 15-O-(beta-D-glucuronosyl)-prostaglandin B1Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and prostaglandin B1 (cytosol to extracellular)
  3. prostaglandin B1 + UDP-alpha-D-glucuronate = 15-O-(beta-D-glucuronosyl)-prostaglandin B1 + UDP + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, UGT1A9 and 3 moreextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A4extracellular space, cytosol

• (R)-noradrenaline 4'-O-sulfateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and noradrenaline (cytosol to extracellular)
  3. sulfotransferase (noradrenaline)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3extracellular space, cytosolOne of 2 routes

• L-homocysteine thiolactoneReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Formation of Homocystine
  3. arylesterase (homocysteine-thiolactone)

  Catalysed by SLCO1A2, SLCO1B3, PON1, PON2 and 1 moreextracellular space, cytosol

• ursodeoxycholate 3-sulfateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and ursodeoxycholate (cytosol to extracellular)
  3. ursodeoxycholate + 3'-phosphoadenylyl sulfate = ursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• tauroursodeoxycholate 3-sulfateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and tauroursodeoxycholate (cytosol to extracellular)
  3. tauroursodeoxycholate + 3'-phosphoadenylyl sulfate = tauroursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• glycoursodeoxycholate 3-sulfateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of glycoursodeoxycholate and GSH (cytosol to extracellular)
  3. glycoursodeoxycholate + 3'-phosphoadenylyl sulfate = glycoursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• chenodeoxycholate 3-sulfateReach from here →
  1. transport of glycolithocholate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + 3'-phosphoadenylyl sulfate = chenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• deoxycholateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cytochrome P450 (cholate)

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

• potassium atomReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and serotonin (cytosol to extracellular)
  3. transport of serotonin (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC6A4extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acylamide amidohydrolase

  Catalysed by SLCO1A2, SLCO1B3, FAAHextracellular space, cytosol

• imidazole-4-acetaldehydeReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and histamine (cytosol to extracellular)
  3. amine oxidase copper containing (histamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 1 moreextracellular space, cytosolOne of 2 routes

• folic acidReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. Folate Transport by Oats

  Catalysed by SULT2A1, STS, SLC22A8, SLC22A7cytosol, extracellular spaceOne of 2 routes

• 3,4-dihydroxyphenylacetaldehydeReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. monoamine oxidase (dopamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 3 moreextracellular space, cytosolOne of 2 routes

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. transport of glycolithocholate (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, STSextracellular space, cytosolOne of 3 routes

• CHEBI:28701Reach from here →
  1. transport of glycolithocholate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate:CoA ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosolOne of 3 routes

• CHEBI:28918Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:phenylethanolamine N-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, PNMTextracellular space, cytosol

• N-acetyl-L-cysteineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by SLCO1A2, SLCO1B3, NAGSextracellular space, cytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A35, SLC25A34cytosol, inner side of the membrane, outer side of the membraneOne of 6 routes

• iron(2+)Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. glutathione:dehydroascorbate oxidoreductase
  3. cytochrome b reductase (ascorbate)

  Catalysed by SLCO1A2, SLCO1B3, CYBRD1extracellular space, cytosol

• K(+)Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and serotonin (cytosol to extracellular)
  3. serotonin(out) + K(+)(in) + Na(+)(out) + H(+)(in) = serotonin(in) + K(+)(out) + Na(+)(in) + H(+)(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC6A4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 3 routes

• Cys-tRNA(Cys)Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, CARS1extracellular space, cytosol

• chlorine(.)Reach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. transport of chloride and sulfate (cytosol to extracellular)

  Catalysed by SULT2A1, STS, SLC26A6cytosol, extracellular spaceOne of 3 routes

• hydrogen sulfideReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

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

• D-aspartateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. D-aspartate(in) + sulfate(out) = D-aspartate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-aspartateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. L-aspartate(in) + sulfate(out) = L-aspartate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHEextracellular space, cytosolOne of 3 routes

• oxalateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. oxalate(in) + sulfate(out) = oxalate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC26A2 and 3 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• formic acidReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-Formylglutathione hydrolase

  Catalysed by SLCO1A2, SLCO1B3, ADH1C, ADH1A and 5 moreextracellular space, cytosol

• maleateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. maleate(in) + sulfate(out) = maleate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• malonic acidReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. transport of malonate and sulfate (cytosol to mitochondria)

  Catalysed by SULT2A1, STS, SLC25A10cytosol, mitochondrial matrixOne of 2 routes

• glutarateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. solute carrier organic anion transporter (glycocholate)
  3. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A24extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 12 routes

• (2R,3R)-tartrateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. (2R,3R)-tartrate(in) + sulfate(out) = (2R,3R)-tartrate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (S,S)-tartrateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. (S,S)-tartrate(in) + sulfate(out) = (S,S)-tartrate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3R)-citramalateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. (3R)-citramalate(in) + sulfate(out) = (3R)-citramalate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3S)-citramalateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. (3S)-citramalate(in) + sulfate(out) = (3S)-citramalate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• pentanoateReach from here →
  1. transport of glycolithocholate (cytosol to extracellular)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. pentanoate(in) + estrone 3-sulfate(out) = pentanoate(out) + estrone 3-sulfate(in)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, SLC22A9extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• methylarsonateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Glutathione: 5-HPETE oxidoreductase
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 9 moreextracellular space, cytosol

• thiosulfateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. thiosulfate(in) + sulfate(out) = thiosulfate(out) + sulfate(in)

  Catalysed by SULT2A1, STS, SLC25A14, SLC25A30 and 2 morecytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• di-mu-sulfido-diiron(2+)Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. De novo synthesis of 2Fe2S

  Catalysed by SLCO1A2, SLCO1B3, NDUFAB1, FDXR and 5 moreextracellular space, cytosol, mitochondrial matrix

• fatty acidReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• CHEBI:37946Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. aryl sulfotransferase (dopamine)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A4 and 2 moreextracellular space, cytosol

• (R)-lactic acidReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-Lactoylglutathione hydrolase

  Catalysed by SLCO1A2, SLCO1B3, GLO1, GLOD4 and 2 moreextracellular space, cytosolOne of 2 routes

• (S)-lactic acidReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and prostaglandin A2 (cytosol to extracellular)
  3. Transport of Prostaglandin A2, Lactate Antiport

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1extracellular space, cytosolOne of 4 routes

• L-ornithineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and ornithine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A6extracellular space, cytosolOne of 2 routes

• N-methylserotoninReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and serotonin (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:amine N-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, INMTextracellular space, cytosol

• (5-hydroxyindol-3-yl)acetaldehydeReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and serotonin (cytosol to extracellular)
  3. 5-Hydroxytryptamine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by SLCO1A2, SLCO1B3, MAOA, MAOBextracellular space, cytosolOne of 2 routes

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acid amide hydrolase (2-arachidonoylglycerol)

  Catalysed by SLCO1A2, SLCO1B3, FAAHextracellular space, cytosol