glycocholate

Three steps

• (R)-3,4-dihydroxymandelaldehydeReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and noradrenaline (cytosol to extracellular)
  3. (R)-noradrenaline + O2 + H2O = (R)-3,4-dihydroxymandelaldehyde + H2O2 + NH4(+)

  Catalysed by SLCO1A2, SLCO1B3, MAOA, MAOBextracellular space, cytosol

• O-octanoyl-(R)-carnitineReach from here →
  1. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. octanoyl-CoA + (R)-carnitine = O-octanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2, CRAT and 1 moreinner side of the membrane, outer side of the membraneOne of 3 routes

• CHEBI:18183Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. gamma-glutamyltransferase (alanine)
  3. gamma-glutamylcyclotransferase ((5-L-glutamyl)-L-amino acid)

  Catalysed by SLCO1A2, SLCO1B3, GGT1, GGT5 and 6 moreextracellular space, cytosol

• hydrogen cyanideReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. thiosulfate:cyanide sulfurtranserase

  Catalysed by ABCC4, TSTD1, MPST, TSTinner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 2 routes

• (R)-normetanephrineReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, COMT, LRTOMTextracellular space, cytosol

• glycodeoxycholate 3-sulfateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. glycodeoxycholate + 3'-phosphoadenylyl sulfate = glycodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by ABCC4, SULT2A1inner side of the membrane, outer side of the membrane

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. Formation of Homocystine
  3. 5-methyltetrahydrofolate:L-homocysteine S-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, MTRextracellular space, cytosol

• O-butanoyl-(R)-carnitineReach from here →
  1. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CRATinner side of the membrane, outer side of the membrane

• S-disulfanyl-L-cysteineReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. cystine to cysteine conversion
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by SLCO1A2, SLCO1B3, CARS2extracellular space, cytosol

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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

• glycochenodeoxycholate 3-sulfateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. glycochenodeoxycholate(in) + glutathione(in) + ATP + H2O = glycochenodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. glycochenodeoxycholate + 3'-phosphoadenylyl sulfate = glycochenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by ABCC4, SULT2A1inner side of the membrane, outer side of the membrane

• deoxycholateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. solute carrier organic anion transporter (cholate)
  3. cytochrome P450 (cholate)

  Catalysed by SLCO1A2, SLCO1B3, CYP7A1extracellular space, cytosolOne of 5 routes

• dimethylarsinous acidReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. arsenic triglutathione + 3 [thioredoxin]-dithiol + 3 S-adenosyl-L-methionine = trimethylarsine + 3 [thioredoxin]-disulfide + 3 glutathione + 3 S-adenosyl-L-homocysteine + 3 H(+)
  3. arsenic triglutathione + 2 [thioredoxin]-dithiol + 2 S-adenosyl-L-methionine + H2O = dimethylarsinous acid + 2 [thioredoxin]-disulfide + 3 glutathione + 2 S-adenosyl-L-homocysteine + 2 H(+)

  Catalysed by ABCC4, AS3MTinner side of the membrane, outer side of the membrane

• potassium atomReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acylamide amidohydrolase

  Catalysed by SLCO1A2, SLCO1B3, FAAHextracellular space, cytosol

• trimethylarsineReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. arsenic triglutathione + 3 [thioredoxin]-dithiol + 3 S-adenosyl-L-methionine = trimethylarsine + 3 [thioredoxin]-disulfide + 3 glutathione + 3 S-adenosyl-L-homocysteine + 3 H(+)
  3. arsenic triglutathione + 3 [thioredoxin]-dithiol + 3 S-adenosyl-L-methionine = trimethylarsine + 3 [thioredoxin]-disulfide + 3 glutathione + 3 S-adenosyl-L-homocysteine + 3 H(+)

  Catalysed by ABCC4, AS3MTinner side of the membrane, outer side of the membrane

• imidazole-4-acetaldehydeReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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

• 3,4-dihydroxyphenylacetaldehydeReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate:CoA ligase (AMP-forming)

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

• O-decanoyl-(R)-carnitineReach from here →
  1. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. decanoyl-CoA + (R)-carnitine = O-decanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2, CRATinner side of the membrane, outer side of the membrane

• CHEBI:28918Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A6extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 8 routes

• iron(2+)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. glutathione:dehydroascorbate oxidoreductase
  3. cytochrome b reductase (ascorbate)

  Catalysed by SLCO1A2, SLCO1B3, CYBRD1extracellular space, cytosolOne of 2 routes

• K(+)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  2. cystine to cysteine conversion
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, CARS1extracellular space, cytosol

• a thiolReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. L-cysteinyl-[sulfatase] + 2 a thiol + O2 = an organic disulfide + 3-oxo-L-alanyl-[sulfatase] + hydrogen sulfide + H2O + H(+)

  Catalysed by ABCC4, TSTD1, SUMF1inner side of the membrane, outer side of the membrane

• chlorine(.)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. cystine to cysteine conversion
  3. transport of chloride and cysteine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC6A14extracellular space, cytosolOne of 2 routes

• acetateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of acetylcholine and GSH (cytosol to extracellular)
  3. Acetylcholine aectylhydrolase

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

• formic acidReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-Formylglutathione hydrolase

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

• malonic acidReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. transport of malonate and sulfite (cytosol to mitochondria)

  Catalysed by ABCC4, TSTD1, SLC25A10inner side of the membrane, outer side of the membrane, mitochondrial matrix, cytosolOne of 2 routes

• (S)-dihydroorotateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. (S)-dihydroorotate + a quinone = orotate + a quinol

  Catalysed by ABCC4, SQOR, DHODHinner side of the membrane, outer side of the membrane

• pentanoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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

• nicotinateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. urate(out) + glutathione(in) = urate(in) + glutathione(out)
  3. nicotinate(in) + urate(out) = nicotinate(out) + urate(in)

  Catalysed by ABCC4, SLC22A13, SLC22A12inner side of the membrane, outer side of the membrane

• a carboxylic esterReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O
  3. a carboxylic ester + H2O = an alcohol + a carboxylate + H(+)

  Catalysed by ABCC4, CP, PRDX6, CES2 and 4 moreinner side of the membrane, outer side of the membrane

• methylarsonateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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, cytosolOne of 2 routes

• thiosulfateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. Glutathione: 5-HPETE oxidoreductase
  3. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 8 moreextracellular space, cytosolOne of 11 routes

• di-mu-sulfido-diiron(2+)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• a hydroperoxideReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O
  3. a hydroperoxide + [thioredoxin]-dithiol = an alcohol + [thioredoxin]-disulfide + H2O

  Catalysed by ABCC4, CP, PRDX6, PRDX5 and 4 moreinner side of the membrane, outer side of the membrane