glycolithocholic acid

Three steps

• malonaldehydeReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. thromboxane A synthase (12(S)-HHT)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, TBXAS1extracellular space, cytosolOne of 2 routes

• 3,3',5'-triiodo-L-thyronineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and thyroxine (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. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. leukotriene C4 synthase (GSH)
  3. leukotriene C4 hydrolysis

  Catalysed by SLCO1A2, SLCO1B3, LTC4Sextracellular space, cytosolOne of 11 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by SLCO1A2, SLCO1B3, SLC27A2, ACSL4 and 9 moreextracellular space, cytosol

• choloyl-CoAReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cholate + ATP + CoA = choloyl-CoA + AMP + diphosphate

  Catalysed by SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

• 15-oxoprostaglandin E2Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by SLCO1A2, SLCO1B3, GOT2, GOT1extracellular space, cytosolOne of 3 routes

• L-methionineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and methionine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 8 routes

• N-sulfo-D-glucosamineReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate

  Catalysed by SULT2A1, STS, SGSHcytosol

• L-tryptophanReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and tryptophan (cytosol to extracellular)

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

• glutathioneReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Glutathione: 5-HPETE oxidoreductase
  3. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 8 moreextracellular space, cytosolOne of 16 routes

• L-alanineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. gamma-glutamyltransferase (alanine)

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 4 moreextracellular space, cytosolOne of 16 routes

• L-asparagineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of asparagine and cysteine (cytosol to extracellular)

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

• L-phenylalanineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Formation of Homocystine
  3. L-serine hydro-lyase (adding homocysteine

  Catalysed by SLCO1A2, SLCO1B3, CBSextracellular space, cytosol

• gamma-L-glutamyl-L-cysteineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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

• adenosine 5'-phosphosulfateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. ATP:sulfate adenylyltransferase

  Catalysed by SULT2A1, STS, PAPSS1, PAPSS2cytosolOne of 4 routes

• S-sulfanyl-L-cysteineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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

• hyodeoxycholateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  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 9 routes

• 3-sulfino-L-alanineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:oxygen oxidoreductase

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

• (5-hydroxyindol-3-yl)acetateReach from here →
  1. sulfotransferase (glycolithocholate)
  2. steroid sulfatase (sulfoglycolithocholate)
  3. Transport of 5-Hydroxyindoleacetate

  Catalysed by SULT2A1, STS, SLC4A1cytosol, extracellular spaceOne of 2 routes

• chenodeoxycholoyl-CoAReach from here →
  1. transport of glycolithocholate (cytosol to extracellular)
  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. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. leukotriene C4 synthase (GSH)
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

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

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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

• (R)-adrenalineReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  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

• CHEBI:742324Reach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

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

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX12Bextracellular space, cytosol

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:oxygen 8-oxidoreductase

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

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, FAAHextracellular space, cytosol

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (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, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (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, CYP1A1, CYP1A2 and 3 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.2
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• 7-oxolithocholateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of GSH and ursodeoxycholate (cytosol to extracellular)
  3. ursodeoxycholate + NAD(+) = 7-oxolithocholate + NADH + H(+)

  Catalysed by SLCO1A2, SLCO1B3, HSD17B10extracellular space, cytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

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

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

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

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, PTGS2extracellular space, cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of glycolithocholate and GSH (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

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