chenodeoxycholate

Three steps

• D-glucitolReach 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. Aldehyde Reductase

  Catalysed by GBA2cytosolOne of 3 routes

• CHEBI:17927Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by SLC27A5, BAATcytosol, peroxisome

• butanoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, SLC22A9extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

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

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

• arsenic triglutathioneReach 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. 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 CYP8B1, ABCC4, AS3MTinner side of the membrane, outer side of the membraneOne of 3 routes

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

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

• 15-deoxy-Delta(12,14)-prostaglandin J2-S-(R)-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. 15-deoxy-Delta(12,14)-prostaglandin J2 + glutathione = 15-deoxy-Delta(12,14)-prostaglandin J2-S-(R)-glutathione

  Catalysed by CYP8B1, ABCC4, MGST3inner side of the membrane, outer side of the membrane

• (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach 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,17Z)-eicosapentaenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

• (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach 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,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

• (15S)-hydroxy-(11Z,13E)-eicosadienoateReach 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. (15S)-hydroperoxy-(11Z,13E)-eicosadienoate + 2 glutathione = (15S)-hydroxy-(11Z,13E)-eicosadienoate + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

• (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach 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. (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 2 glutathione = (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX1, GPX4inner side of the membrane, outer side of the membrane

• a hydroxy-1,2-diacyl-glycero-3-phosphocholineReach 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. a hydroperoxy-1,2-diacyl-glycero-3-phosphocholine + 2 glutathione = a hydroxy-1,2-diacyl-glycero-3-phosphocholine + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GPX4inner side of the membrane, outer side of the membrane

• deoxycholate 3-sulfateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cytochrome P450 (cholate)
  3. deoxycholate + 3'-phosphoadenylyl sulfate = deoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by CYP8B1, CYP7A1, SULT2A1cytosol

• (5Z)-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-7-enoyl-CoA)

  Catalysed by SLC27A5, BAAT, HADHA, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 2 routes

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (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, SLCO1B1, UGT1A9 and 5 moreextracellular space, cytosol

• 20-O-(beta-D-glucuronosyl)-(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. 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, SLCO1B1, UGT2B7 and 2 moreextracellular space, cytosol

• 15-O-(beta-D-glucuronosyl)-prostaglandin B1Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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, SLCO1B1, UGT1A9 and 3 moreextracellular space, cytosol

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

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

• (7Z)-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 ((7Z)-tetradecenoic acid)

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

• serotonin O-sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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 (chenodiol)
  2. transport of noradrenaline (cytosol to extracellular)
  3. sulfotransferase (noradrenaline)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3extracellular space, cytosolOne of 2 routes

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

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

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by SLC27A5, BAAT, HADHA, ACADVL and 1 morecytosol, peroxisome, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by SLC27A5, BAAT, ECHS1, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A5, BAAT, ECHS1, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 2 routes

• 3-(glutathion-S-yl)-4-hydroxynonanalReach 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. (E)-4-hydroxynon-2-enal + glutathione = 3-(glutathion-S-yl)-4-hydroxynonanal

  Catalysed by CYP8B1, ABCC4, GSTP1inner side of the membrane, outer side of the membrane

• ursodeoxycholate 3-sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (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 (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (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 (chenodiol)
  2. transport of glycoursodeoxycholate (cytosol to extracellular)
  3. glycoursodeoxycholate + 3'-phosphoadenylyl sulfate = glycoursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• glycochenodeoxycholate 3-sulfateReach from here →
  1. chenodeoxycholate + ATP + CoA = chenodeoxycholoyl-CoA + AMP + diphosphate
  2. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)
  3. glycochenodeoxycholate + 3'-phosphoadenylyl sulfate = glycochenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLC27A5, BAAT, SULT2A1

• a quinolReach 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. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol

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

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

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

• imidazole-4-acetaldehydeReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of histamine (cytosol to extracellular)
  3. amine oxidase copper containing (histamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 1 moreextracellular space, cytosolOne of 2 routes

• CHEBI:27540Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A5, BAAT, ACSM4, ACSM1 and 4 morecytosol, peroxisomeOne of 6 routes

• 3,4-dihydroxyphenylacetaldehydeReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. monoamine oxidase (dopamine)

  Catalysed by SLCO1A2, SLCO1B3, AOC2, AOC1 and 3 moreextracellular space, cytosolOne of 2 routes

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

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

• 5(S)-HETEReach 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: 5-HPETE oxidoreductase

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, GPX5 and 8 moreextracellular space, cytosolOne of 2 routes

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  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:28918Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:phenylethanolamine N-methyltransferase

  Catalysed by SLCO1A2, SLCO1B3, PNMTextracellular space, cytosol

• a dicarboxylateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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 4 routes

• L-ascorbic acidReach 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. L-dehydroascorbate + 2 glutathione = glutathione disulfide + L-ascorbate

  Catalysed by CYP8B1, ABCC4, CLIC1, GSTO1 and 1 moreinner side of the membrane, outer side of the membrane

• K(+)Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of 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 membrane

• hydrogen sulfideReach 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. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by CYP8B1, ABCC4, TSTD1inner side of the membrane, outer side of the membrane

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

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

• an alcoholReach 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. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, CP, PRDX6inner side of the membrane, outer side of the membrane

• glutarateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. solute carrier organic anion transporter (glycocholate)
  3. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A24extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 12 routes

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

• fatty acidReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes

• alpha-lactoseReach 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. UDP-alpha-D-galactose:D-glucose 4-beta-D-galactosyltransferase

  Catalysed by GBA2, B4GALT2, LALBA, B4GALT1Golgi apparatus