cholate

Three steps

• 11beta-prostaglandin F2Reach from here →
  1. solute carrier organic anion transporter (cholate)
  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

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. Cholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by SLC27A2, SLC27A5, BAAT, HADHA and 2 moreendoplasmic reticulum, peroxisome, mitochondrial matrix

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. solute carrier organic anion transporter (cholate)
  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

• (7Z)-hexadecenoyl-CoAReach from here →
  1. Cholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. Cholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 4 routes

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  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 (cholate)
  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 (cholate)
  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 (cholate)
  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. cholate(in) + glutathione(in) + ATP + H2O = cholate(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. cholate(in) + glutathione(in) + ATP + H2O = cholate(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. cholate(in) + glutathione(in) + ATP + H2O = cholate(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 (cholate)
  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 (cholate)
  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