chenodeoxycholate

Three steps

• (3Z)-dodecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A5, BAAT, HADHA, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 3 routes

• N(tau)-methylhistamineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of histamine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:histamine N-tele-methyltransferase

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

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A5, BAAT, SLC27A2cytosol, peroxisome, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A5, BAAT, SLC27A2cytosol, peroxisomeOne of 7 routes

• hyodeoxycholateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of lithocholate (cytosol to extracellular)
  3. cytochrome P450 (lithocholate)

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• S-sulfanylglutathioneReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, SQORextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

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

• monodehydro-L-ascorbate radicalReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. dopamine + 2 L-ascorbate + O2 = (R)-noradrenaline + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosol

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

  Catalysed by SLC27A5, BAAT, ACSM4, ACSM1 and 4 morecytosol, peroxisomeOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 4 routes

• (9Z)-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 (palmitolate)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 11 routes

• D-glucose 6-phosphateReach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. D-glucose + ADP = D-glucose 6-phosphate + AMP + H(+)

  Catalysed by GBA2, ADPGKOne of 2 routes

• L-cysteinylglycineReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. glutathione gamma-glutamylaminopeptidase

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, GGTLC3 and 5 moreextracellular space, cytosolOne of 6 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1Bcytosol, peroxisome

• leukotriene D4Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of leukotriene C4 (cytosol to extracellular)
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, GGT1 and 1 moreextracellular space, cytosol

• CHEBI:63544Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 7 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol, endoplasmic reticulumOne of 2 routes

• ubiquinol-10Reach 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. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10

  Catalysed by CYP8B1, ABCC4, SQORinner side of the membrane, outer side of the membrane

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

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

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

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 10 routes

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

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 9 routes

• (R)-adrenalineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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

• (2E)-octadecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

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

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 7 routes

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

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

• (11Z)-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 (cis-gondoic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 7 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

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

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

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

• (15Z)-tetracosenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

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

• (17Z)-hexacosenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

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

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

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

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

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

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

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

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 7 routes

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

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

• (9Z)-heptadecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

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

• (11Z,14Z,17Z)-eicosatrienoyl-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,17Z)-eicosatrienoic acid)

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

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

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

• (11Z)-octadecenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 3 routes

• (12R)-hydroperoxy-(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 + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX12Bextracellular space, cytosol

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

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

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

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

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

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 4 routes

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

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 4 routes

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

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 7 routes