prostaglandin E2

Three steps

• N(tau)-methylhistamineReach from here →
  1. transport of GSH and prostaglandin E2 (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

• (3S)-citramalyl-CoAReach 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. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

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

• 5-amino-2-oxopentanoateReach 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. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

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

• hyodeoxycholateReach from here →
  1. transport of GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:oxygen oxidoreductase

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

• (4R)-4-hydroxy-2-oxoglutarateReach 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. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

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

• (5-hydroxyindol-3-yl)acetateReach 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. Transport of 5-Hydroxyindoleacetate

  Catalysed by SLC22A6, SLC25A35, SLC25A34, SLC4A1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• chenodeoxycholoyl-CoAReach from here →
  1. transport of prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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

• (4S)-4-hydroxy-2-oxoglutarateReach 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. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

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

• methyl (indol-3-yl)acetateReach from here →
  1. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)
  2. (indol-3-yl)acetate(out) + a dicarboxylate(in) = (indol-3-yl)acetate(in) + a dicarboxylate(out)
  3. S-adenosyl-L-methionine:(indol-3-yl)acetate O-methyltransferase

  Catalysed by SLC22A6, SLC22A8, COMT, LRTOMTinner side of the membrane, outer side of the membrane, cytosol

• CHEBI:730073Reach 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

• a 1-(1-hydroxyalkyl)-sn-glycerolReach 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. 1-O-(1,2-saturated-alkyl)-sn-glycerol + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = a 1-(1-hydroxyalkyl)-sn-glycerol + (6R)-L-erythro-6,7-dihydrobiopterin + H2O

  Catalysed by SLC22A6, SLC22A8, AGMOinner side of the membrane, outer side of the membrane

• CHEBI:742324Reach from here →
  1. transport of GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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

• hexanedioyl-CoAReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate + succinyl-CoA = glutaryl-CoA + succinate
  3. hexanedioate + glutaryl-CoA = hexanedioyl-CoA + glutarate

  Catalysed by SLC22A8, SUGCTinner side of the membrane, outer side of the membraneOne of 3 routes

• 11,12-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 = 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 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 = 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 GSH and prostaglandin E2 (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

• O-dodecanoyl-R-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. dodecanoyl-CoA + (R)-carnitine = O-dodecanoyl-R-carnitine + CoA

  Catalysed by SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• 7-oxolithocholateReach from here →
  1. transport of GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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 GSH and prostaglandin E2 (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

• thio-Mo-molybdopterinReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by SLCO1A2, SLCO1B3, MOCOSextracellular space, cytosol

• (12R)-hydroxy-(5Z,8Z,10E,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 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP2C9extracellular space, cytosol

• 14,15-epoxy-(5Z,8Z,11Z)-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 25 moreextracellular space, cytosolOne of 4 routes

• 8,9-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. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ABHD16Aextracellular space, cytosol

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-octadecanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-eicosanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-(9Z)-octadecenoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. 4,8-dimethylnonanoyl-CoA + (R)-carnitine = O-4,8-dimethylnonanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CPT2, CRAT, CROTinner side of the membrane, outer side of the membrane

• O-hexanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. hexanoyl-CoA + (R)-carnitine = O-hexanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CRATinner side of the membrane, outer side of the membrane

• O-3-oxobutanoyl-(R)-carnitineReach from here →
  1. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A8, CRATinner side of the membrane, outer side of the membrane

• 11beta-prostaglandin F2Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of GSH and prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, AKR1C3 and 1 moreextracellular space, cytosol

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. transport of prostaglandin E2 (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP3A7extracellular space, cytosol

• (18R)-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 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP4F8extracellular space, cytosol

• prostaglandin H1Reach from here →
  1. transport of GSH and prostaglandin E2 (cytosol to extracellular)
  2. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

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