cholate

Three steps

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 5 moreendoplasmic reticulum, peroxisome, cytosolOne of 15 routes

• 15-oxoprostaglandin E2Reach from here →
  1. solute carrier organic anion transporter (cholate)
  2. transport of GSH and 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 (cholate)
  2. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  3. (13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-13-enoate:NADP+ 15-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, CBR3 and 2 moreextracellular space, cytosolOne of 3 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1extracellular space, cytosolOne of 2 routes

• 15-oxo-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. Glutathione: 15-HPETE oxidoreductase
  3. (15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate:NADP+ 15-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 7 moreextracellular space, cytosolOne of 3 routes

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

  Catalysed by SLCO1A2, SLCO1B3, ALOX5, ALOX15 and 1 moreextracellular space, cytosol

• thromboxane A2Reach from here →
  1. solute carrier organic anion transporter (cholate)
  2. transport of GSH and thromboxane B2 (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 (cholate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15B, ALOX15 and 1 moreextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, ALOX5extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, HDCextracellular space, cytosol

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by SLCO1A2, SLCO1B3, GOT2, GOT1extracellular space, cytosolOne of 4 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ASAH1 and 3 moreendoplasmic reticulum, peroxisome, Golgi apparatusOne of 2 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, SAT1 and 1 moreendoplasmic reticulum, peroxisome, cytosolOne of 3 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, NAGSendoplasmic reticulum, peroxisome, mitochondrial matrixOne of 9 routes

• L-tryptophanReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. transport of cysteine and tryptophan (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 4 routes

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

  Catalysed by SLC27A2, SLC27A5, BAATendoplasmic reticulum, peroxisome, mitochondrial matrixOne of 17 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, NAGSendoplasmic reticulum, peroxisome, mitochondrial matrixOne of 5 routes

• L-phenylalanineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. transport of cysteine and phenylalanine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 6 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, NAGSendoplasmic reticulum, peroxisome, mitochondrial matrixOne of 2 routes

• gamma-L-glutamyl-L-cysteineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by SLCO1A2, SLCO1B3, GCLC, GCLMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ASAH1 and 3 moreendoplasmic reticulum, peroxisome, Golgi apparatusOne of 2 routes

• trans-4-hydroxy-L-prolineReach from here →
  1. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)

  Catalysed by ABCC4, SQOR, PRODH2inner side of the membrane, outer side of the membrane

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

  Catalysed by SLC27A2, SLC27A5, BAAT, HADHA and 2 moreendoplasmic reticulum, peroxisome, mitochondrial matrixOne of 3 routes

• S-sulfanyl-L-cysteineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by SLCO1A2, SLCO1B3, CARS2extracellular space, cytosol

• N(tau)-methylhistamineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. transport of GSH and 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. Cholate: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 SLC27A2, SLC27A5, BAATendoplasmic reticulum, peroxisomeOne of 3 routes

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

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, FAAH, PM20D1extracellular space, cytosol

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

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

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

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosolOne of 20 routes

• L-prolineReach from here →
  1. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. L-proline + a quinone = (S)-1-pyrroline-5-carboxylate + a quinol + H(+)

  Catalysed by ABCC4, SQOR, PRODH, PRODH2inner side of the membrane, outer side of the membrane

• 3-sulfino-L-alanineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. cystine to cysteine conversion
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, CDO1extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSM4 and 5 moreendoplasmic reticulum, peroxisome, cytosolOne of 7 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, CPT1A and 2 moreendoplasmic reticulum, peroxisome, cytosolOne of 4 routes

• (9Z)-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 (palmitolate)

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 11 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, CPT1A and 1 moreendoplasmic reticulum, peroxisome, cytosol

• chenodeoxycholoyl-CoAReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + ATP + CoA = chenodeoxycholoyl-CoA + AMP + diphosphate

  Catalysed by SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

• leukotriene D4Reach from here →
  1. solute carrier organic anion transporter (cholate)
  2. leukotriene C4 synthase (GSH)
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by SLCO1A2, SLCO1B3, LTC4S, GGT1 and 1 moreextracellular space, cytosol

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 7 routes

• 18-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. cytochrome P450 (arachidonate)

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

• 3-demethylubiquinol-10Reach from here →
  1. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10
  3. 3-demethylubiquinol-10 + S-adenosyl-L-methionine = ubiquinol-10 + S-adenosyl-L-homocysteine + H(+)

  Catalysed by ABCC4, SQOR, COQ3inner side of the membrane, outer side of the membrane

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 5 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 10 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 9 routes

• (R)-adrenalineReach from here →
  1. solute carrier organic anion transporter (cholate)
  2. transport of GSH and 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. Cholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, SLC27A5, BAAT, CPT1A and 2 moreendoplasmic reticulum, peroxisome, cytosolOne of 3 routes

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

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

• CHEBI:730073Reach from here →
  1. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. urate(out) + glutathione(in) = urate(in) + glutathione(out)
  3. Peroxidase

  Catalysed by ABCC4, SLC22A13, MPOinner side of the membrane, outer side of the membrane, nucleusOne of 3 routes

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

  Catalysed by SLC27A2, SLC27A5, BAAT, ACSL4 and 6 moreendoplasmic reticulum, peroxisome, cytosolOne of 9 routes