chenodeoxycholate

Three steps

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 5 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisome

• (13Z)-eicosenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 5 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, CYP1A1 and 4 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by SLC27A5, BAAT, CRAT, CROTcytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by SLC27A5, BAAT, ACAA1, HSD17B4 and 2 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 2 routes

• pristanoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. fatty-acid-CoA ligase

  Catalysed by SLC27A5, BAAT, SLC27A2cytosol, peroxisomeOne of 2 routes

• undecanoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by SLC27A5, BAAT, ACSM4, ACSM1 and 4 morecytosol, peroxisomeOne of 3 routes

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  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 CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• glycodeoxycholateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cytochrome P450 (cholate)
  3. Glycodeoxycholate amidohydrolase

  Catalysed by CYP8B1, CYP7A1cytosolOne of 2 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 26 moreextracellular space, cytosolOne of 4 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 25 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 (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, ABHD16Aextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by SLC27A5, BAAT, ACADM, ECHS1 and 2 morecytosol, peroxisome, mitochondrial matrix

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, AKR1C3 and 1 moreextracellular space, cytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. chenodeoxycholate: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 SLC27A5, BAAT, HADHA, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrix

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  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. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 8 routes

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

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  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 CYP8B1, ABCC4, PTGES, MGST3 and 4 moreinner side of the membrane, outer side of the membrane

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  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 CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, TBXAS1 and 2 moreextracellular space, cytosol

• an S-substituted glutathioneReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by CYP8B1, ABCC4, GSTT4, GSTA4 and 21 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, CYP4F8extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PTGES and 2 moreextracellular space, cytosolOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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, SLCO1B1, CYP4F8extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15Bextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15Bextracellular space, cytosol

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate + 2 glutathione = (13S)-hydroxy-(9Z,11E)-octadecadienoate + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX1, GSTA1 and 2 moreinner side of the membrane, outer side of the membrane