glycocholate

Three steps

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. cytochrome P450 (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP4F8extracellular space, cytosol, endoplasmic reticulumOne of 2 routes

• 3-demethylubiquinol-10Reach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10
  3. 3-demethylubiquinol-10 + S-adenosyl-L-methionine = ubiquinol-10 + S-adenosyl-L-homocysteine + H(+)

  Catalysed by ABCC4, SQOR, COQ3inner side of the membrane, outer side of the membrane

• (R)-adrenalineReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and noradrenaline (cytosol to extracellular)
  3. (R)-noradrenaline + S-adenosyl-L-methionine = (R)-adrenaline + S-adenosyl-L-homocysteine + H(+)

  Catalysed by SLCO1A2, SLCO1B3, PNMTextracellular space, cytosol

• CHEBI:730073Reach 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. Peroxidase

  Catalysed by ABCC4, SLC22A13, MPOinner side of the membrane, outer side of the membrane, nucleusOne of 3 routes

• CHEBI:742324Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

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

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX12Bextracellular space, cytosol

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX12extracellular space, cytosolOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, FAAHextracellular space, cytosol

• hexanedioyl-CoAReach from here →
  1. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  2. glutarate + succinyl-CoA = glutaryl-CoA + succinate
  3. hexanedioate + glutaryl-CoA = hexanedioyl-CoA + glutarate

  Catalysed by SLC22A24, SUGCTinner side of the membrane, outer side of the membraneOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 3 moreextracellular space, cytosol

• 20-oxo-(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. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• O-dodecanoyl-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. dodecanoyl-CoA + (R)-carnitine = O-dodecanoyl-R-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

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

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

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1A2, SLCO1B3, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1A2, SLCO1B3, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, PTGS2extracellular space, cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX12extracellular space, cytosolOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. cystine to cysteine conversion
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by SLCO1A2, SLCO1B3, MOCOSextracellular space, cytosol

• an alkyl sulfateReach 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. an alcohol + 3'-phosphoadenylyl sulfate = an alkyl sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by ABCC4, CP, PRDX6, SULT2B1 and 2 moreinner side of the membrane, outer side of the membrane

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 25 moreextracellular space, cytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, 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. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• O-tetradecanoyl-(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. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-octadecanoyl-(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. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-eicosanoyl-(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. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-(9Z)-octadecenoyl-(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. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-4,8-dimethylnonanoyl-(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. 4,8-dimethylnonanoyl-CoA + (R)-carnitine = O-4,8-dimethylnonanoyl-(R)-carnitine + CoA

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

• O-hexanoyl-(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. hexanoyl-CoA + (R)-carnitine = O-hexanoyl-(R)-carnitine + CoA

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

• O-3-oxobutanoyl-(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. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA

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

• 11beta-prostaglandin F2Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, AKR1C3 and 1 moreextracellular space, cytosol

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  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 SLCO1A2, SLCO1B3, SLCO1B1, CYP3A7extracellular space, cytosol

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, TBXAS1 and 2 moreextracellular space, cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (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 SLCO1A2, SLCO1B3, CYP4F8extracellular space, cytosol

• prostaglandin H1Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, PTGES and 2 moreextracellular space, cytosolOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, CYP4F8extracellular space, cytosol

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by ABCC4, PTGES, MGST3, GPX1 and 4 moreinner side of the membrane, outer side of the membrane

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by ABCC4, PTGES, MGST3, GPX1 and 4 moreinner side of the membrane, outer side of the membrane

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by ABCC4, PTGES, MGST3, GPX1 and 4 moreinner side of the membrane, outer side of the membrane

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15Bextracellular space, cytosol

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15Bextracellular space, cytosol