chenodeoxycholate

Three steps

• CHEBI:37946Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. aryl sulfotransferase (dopamine)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A4 and 2 moreextracellular space, cytosol

• D-glucopyranose 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. ATP:D-glucose 6-phosphotransferase

  Catalysed by GBA2, HK1, GCK, HK2 and 2 morecytosolOne of 5 routes

• (S)-lactic acidReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. Transport of Prostaglandin A2, Lactate Antiport

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

• tert-butanolReach 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. tert-butyl hydroperoxide + 2 glutathione = tert-butanol + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, CLIC2, GPX1 and 3 moreinner side of the membrane, outer side of the membrane

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

  Catalysed by SLCO1A2, SLCO1B3, INMTextracellular space, cytosol

• (5-hydroxyindol-3-yl)acetaldehydeReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of serotonin (cytosol to extracellular)
  3. 5-Hydroxytryptamine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by SLCO1A2, SLCO1B3, MAOA, MAOBextracellular space, cytosolOne of 2 routes

• gamma-Glu-AlaReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, GGT1 and 5 moreextracellular space, cytosol

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

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 2 routes

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

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

• malonaldehydeReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. thromboxane A synthase (12(S)-HHT)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, TBXAS1extracellular space, cytosolOne of 2 routes

• 3,3',5'-triiodo-L-thyronineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by SLCO1A2, SLCO1B3, DIO1, DIO3extracellular space, cytosol

• glycineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by SLC27A5, BAAT, GLYAT, GLYATL2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 14 routes

• (R)-methylmalonyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by SLC27A5, BAAT, ALDH6A1cytosol, peroxisome, mitochondrial matrixOne of 2 routes

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

  Catalysed by SLC27A5, BAATcytosol, peroxisome, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by SLC27A5, BAAT, ACP2cytosol, peroxisome, lysosomeOne of 2 routes

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

  Catalysed by SLC27A5, BAATcytosol, peroxisome, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by SLC27A5, BAAT, ACAA1, MYO5Bcytosol, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-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 (gamma-linolenate)

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

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, SLC27A2 and 10 moreextracellular space, cytosol

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

  Catalysed by SLC27A5, BAAT, ACSM4, ACSM1 and 4 morecytosol, peroxisomeOne of 9 routes

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

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

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

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

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

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 12 routes

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

  Catalysed by SLC27A5, BAAT, SUCLG1, SUCLG2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-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)-octadecadienoic acid)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 13 routes

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

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

• octanoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SLC27A5, BAAT, CROTcytosol, peroxisome, mitochondrial matrixOne of 20 routes

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

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 5 routes

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

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 5 morecytosol, peroxisomeOne of 15 routes

• 15-oxoprostaglandin E2Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2 + NAD(+) = 15-oxoprostaglandin E2 + NADH + H(+)

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

• 15-oxoprostaglandin E1Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. (13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-13-enoate:NADP+ 15-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CBR3 and 2 moreextracellular space, cytosolOne of 3 routes

• 15-oxoprostaglandin D2Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. 15-dehydro-prostaglandin D2 reduction

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 2 routes

• (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach 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: 15-HPETE oxidoreductase

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

• (12S)-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 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX5 and 2 moreextracellular space, cytosol

• thromboxane A2Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. thromboxane A2 hydrolysis

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosol, endoplasmic reticulumOne of 4 routes

• (15S)-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 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15B and 2 moreextracellular space, cytosol

• (5S)-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 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX5extracellular space, cytosol

• (R)-S-lactoylglutathioneReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, GLO1 and 1 moreextracellular space, cytosolOne of 3 routes

• L-dopaReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. L-dopa + H(+) = dopamine + CO2

  Catalysed by SLCO1A2, SLCO1B3, DDCextracellular space, cytosol

• L-histidineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of histamine (cytosol to extracellular)
  3. L-histidine + H(+) = histamine + CO2

  Catalysed by SLCO1A2, SLCO1B3, HDCextracellular space, cytosol

• S-formylglutathioneReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. alcohol dehydrogenase (formaldehyde)

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, ADH1C and 5 moreextracellular space, cytosolOne of 2 routes

• sphing-4-enineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A5, BAAT, ASAH1, ACER2 and 2 morecytosol, peroxisome, Golgi apparatusOne of 2 routes

• spermidineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A5, BAAT, SAT1, SAT2cytosol, peroxisomeOne of 3 routes

• L-methionineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SLC27A5, BAAT, NAGScytosol, peroxisome, mitochondrial matrix

• L-alanineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SLC27A5, BAATcytosol, peroxisome, mitochondrial matrix

• L-asparagineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by SLC27A5, BAAT, NAGScytosol, peroxisome, mitochondrial matrix

• L,L-cystathionineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by SLC27A5, BAAT, NAGScytosol, peroxisome, mitochondrial matrix

• glutathione disulfideReach 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 35 routes

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

  Catalysed by SLC27A5, BAAT, ASAH1, ACER2 and 2 morecytosol, peroxisome, Golgi apparatusOne of 2 routes

• 5-oxo-L-prolineReach 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. glutathione = L-cysteinylglycine + 5-oxo-L-proline

  Catalysed by CYP8B1, ABCC4, CHAC2, CHAC1inner side of the membrane, outer side of the membrane