prostaglandin E2

Three steps

• (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP2C8 and 5 moreextracellular space, cytosol

• (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP2C9, CYP2J2extracellular space, cytosol

• (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP2D6 and 4 moreextracellular space, cytosol

• 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 4 routes

• 17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 2 routes

• 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1extracellular space, cytosol

• pregnenolone sulfateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. Steryl-Sulfatase

  Catalysed by SLC22A6, SLC25A35, SLC25A34, STSinner side of the membrane, outer side of the membrane, Golgi apparatusOne of 2 routes

• androsterone 3alpha-sulfateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. steroid sulfatase (androsterone sulfate)

  Catalysed by SLC22A6, SLC25A35, SLC25A34, STSinner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4, CYP2C9extracellular space, cytosol

• prostaglandin J2Reach from here →
  1. scavenger receptor class F (prostaglandin A2)
  2. Transport of Prostaglandin A2, Lactate Antiport
  3. Transport of Prostaglandin J2, Lactate Antiport

  Catalysed by SCARF2cytosol, extracellular spaceOne of 4 routes

• dopamine 3-O-sulfateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. dopamine + 3'-phosphoadenylyl sulfate = dopamine 3-O-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT1B1, SULT1A3 and 2 moreextracellular space, cytosol

• dopamine 4-O-sulfateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. Dopamine 4-O-Sulfotransferase

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A1extracellular space, cytosolOne of 2 routes

• hyocholateReach from here →
  1. transport of prostaglandin E2 (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. Chenodeoxycholic acid 6alpha-hydroxylase

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15extracellular space, cytosol

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLCO1A2, SLCO1B3, PM20D1extracellular space, cytosol

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 2 routes

• cholesterol sulfateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. Steryl-Sulfatase

  Catalysed by SLC22A6, SLC25A35, SLC25A34, STSinner side of the membrane, outer side of the membrane, Golgi apparatusOne of 2 routes

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP2C9extracellular space, cytosol

• chenodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. transport of prostaglandin E2 (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + UDP-alpha-D-glucuronate = chenodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by SLCO1A2, SLCO1B3, UGT2A2, UGT1A3extracellular space, cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. steroid sulfatase (5-alpha-dihydrotestosterone)

  Catalysed by SLC22A6, SLC25A35, SLC25A34, STSinner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• acetoacetateReach from here →
  1. scavenger receptor class F (prostaglandin A2)
  2. Transport of Prostaglandin A2, Lactate Antiport
  3. transport of acetoacetate and L-lactate (cytosol to extracellular)

  Catalysed by SCARF2, SLC16A4, SLC16A5, SLC16A7 and 2 morecytosol, extracellular spaceOne of 6 routes

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 5 moreextracellular space, cytosol

• an aryl sulfateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SLC22A6, SLC25A35, SLC25A34, ARSL and 5 moreinner side of the membrane, outer side of the membrane

• beta-D-glucosyl-(1->3)-O-chenodeoxycholateReach from here →
  1. transport of prostaglandin E2 (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. 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(+)

  Catalysed by SLCO1A2, SLCO1B3, GBA2extracellular space, cytosolOne of 2 routes

• L-cystine-bis-glycineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. 2 L-cysteinylglycine + [protein]-disulfide = L-cystine-bis-glycine + [protein]-dithiol

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 5 moreextracellular space, cytosol

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by SLCO1A2, SLCO1B3extracellular space, cytosolOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

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

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of GSH and prostaglandin G2 (cytosol to extracellular)
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, PTGESextracellular space, cytosol

• cholineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of acetylcholine and GSH (cytosol to extracellular)
  3. Acetylcholine aectylhydrolase

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHEextracellular space, cytosolOne of 5 routes

• acetylpyruvateReach from here →
  1. prostaglandin E2(out) + 2 (S)-lactate(in) = prostaglandin E2(in) + 2 (S)-lactate(out)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by SLCO2A1, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membrane

• all-trans-retinoic acidReach from here →
  1. scavenger receptor class F (prostaglandin A2)
  2. Transport of Prostaglandin A2, Lactate Antiport
  3. transport of L-lactate and retinoate (cytosol to extracellular)

  Catalysed by SCARF2, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 4 routes

• arachidonoyl-CoAReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, SLC27A2, ACSL4 and 6 moreextracellular space, cytosolOne of 3 routes

• CHEBI:15519Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. Cholate:CoA ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, SLC27A2, SLC27A5extracellular space, cytosol, endoplasmic reticulum

• (S)-malateReach from here →
  1. prostaglandin E2(out) + 2 (S)-lactate(in) = prostaglandin E2(in) + 2 (S)-lactate(out)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by SLCO2A1, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membraneOne of 6 routes

• L-leucineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and leucine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A9, SLC3A1extracellular space, cytosolOne of 3 routes

• 12(S)-HPETEReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX12extracellular space, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. Glutathione: 5-HPETE oxidoreductase
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 7 moreextracellular space, cytosolOne of 6 routes

• 5(S)-HPETEReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX5extracellular space, cytosol

• (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(out) + a dicarboxylate(in) = (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(in) + a dicarboxylate(out)
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin

  Catalysed by SLC22A6, SLC22A8, TPH1, TPH2inner side of the membrane, outer side of the membraneOne of 3 routes

• CHEBI:15699Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and homoserine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 3 routes

• formateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ADH1C, ADH1A and 5 moreextracellular space, cytosol

• malonateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. malonate(in) + sulfate(out) = malonate(out) + sulfate(in)

  Catalysed by SLC22A6, SLC25A35, SLC25A34, SLC25A14 and 2 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:15971Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and histidine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A6extracellular space, cytosolOne of 2 routes

• (R)-lactateReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-lactoylglutathione + H2O = (R)-lactate + glutathione + H(+)

  Catalysed by SLCO1A2, SLCO1B3, GLO1, GLOD4 and 1 moreextracellular space, cytosol

• octan-1-olReach from here →
  1. transport of prostaglandin E2 (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. octyl beta-D-glucose + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + octan-1-ol

  Catalysed by SLCO1A2, SLCO1B3, GBA2extracellular space, cytosol

• ureaReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. urate(in) + glutarate(out) = urate(out) + glutarate(in)
  3. Peroxidase

  Catalysed by SLC22A8, MPOinner side of the membrane, outer side of the membrane, nucleusOne of 3 routes

• 2-methyl-3-oxopropanoic acidReach from here →
  1. prostaglandin E2(out) + 2 (S)-lactate(in) = prostaglandin E2(in) + 2 (S)-lactate(out)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by SLCO2A1, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membrane, mitochondrial matrix