prostaglandin F2alpha

Three steps

• (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP1A1, CYP2C8, CYP2D6 and 4 moreextracellular space, cytosol

• (8S,9R)-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP2C9, CYP2J2extracellular space, cytosol

• (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP1A1, CYP2D6, CYP2C9 and 3 moreextracellular space, cytosol

• 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 4 routes

• 17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 2 routes

• 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP1A1extracellular space, cytosol

• pregnenolone sulfateReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP3A4, CYP2C9extracellular space, cytosol

• dopamine 3-O-sulfateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. dopamine + 3'-phosphoadenylyl sulfate = dopamine 3-O-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1B1 and 3 moreextracellular space, cytosol

• dopamine 4-O-sulfateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. Dopamine 4-O-Sulfotransferase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3 and 1 moreextracellular space, cytosolOne of 2 routes

• hyocholateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. Chenodeoxycholic acid 6alpha-hydroxylase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• prostaglandin A2-S-(R)-glutathioneReach from here →
  1. carbonyl reductase (NADPH) (prostaglandin F2alpha)
  2. scavenger receptor class F (prostaglandin A2)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione

  Catalysed by CBR3, CBR1, AKR1C3, DHRS4 and 3 morecytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. carbonyl reductase (NADPH) (prostaglandin F2alpha)
  2. scavenger receptor class F (prostaglandin A2)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione

  Catalysed by CBR3, CBR1, AKR1C3, DHRS4 and 3 morecytosol

• prostaglandin J2-S-(R)-glutathioneReach from here →
  1. aldo-keto reductase (prostaglandin D2)
  2. prostaglandin J2 hydrolysis
  3. prostaglandin J2 + glutathione = prostaglandin J2-S-(R)-glutathione

  Catalysed by AKR1C3, GSTA1, GSTP1, GSTM1cytosol

• prostaglandin J2-S-(S)-glutathioneReach from here →
  1. aldo-keto reductase (prostaglandin D2)
  2. prostaglandin J2 hydrolysis
  3. prostaglandin J2 + glutathione = prostaglandin J2-S-(S)-glutathione

  Catalysed by AKR1C3, GSTP1, GSTM1cytosol

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX15extracellular space, cytosol

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX15extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLCO1B1, PM20D1extracellular space, cytosol

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 2 routes

• cholesterol sulfateReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (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 SLCO1B1, CYP2C9extracellular space, cytosol

• chenodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. transport of prostaglandin F2alpha (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 SLCO1B1, SLCO1A2, SLCO1B3, UGT2A2 and 1 moreextracellular space, cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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. 15-keto-prostaglandin F2alpha reduction
  2. Transport of 15-Keto-Prostaglandin F2A, Lactate Antiport
  3. transport of acetoacetate and L-lactate (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A8 and 1 morecytosol, extracellular spaceOne of 6 routes

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by SLCO2A1, GGTLC3, GGT1, GGT5 and 4 moreextracellular space, cytosol

• an aryl sulfateReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 F2alpha (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 SLCO1B1, SLCO1A2, SLCO1B3, GBA2extracellular space, cytosolOne of 2 routes

• L-cystine-bis-glycineReach from here →
  1. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. 2 L-cysteinylglycine + [protein]-disulfide = L-cystine-bis-glycine + [protein]-dithiol

  Catalysed by SLCO2A1, GGTLC3, GGT1, GGT5 and 4 moreextracellular space, cytosol

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by SLCO1B1extracellular space, cytosolOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by SLCO1B1, FAAH, PM20D1extracellular space, cytosol

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of prostaglandin G2 (cytosol to extracellular)
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by SLCO1B1, PTGESextracellular space, cytosol

• cholineReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of acetylcholine (cytosol to extracellular)
  3. Acetylcholine aectylhydrolase

  Catalysed by SLCO1B1, SLCO1B3, BCHE, ACHEextracellular space, cytosolOne of 5 routes

• acetylpyruvateReach from here →
  1. prostaglandin F2alpha(out) + 2 (S)-lactate(in) = prostaglandin F2alpha(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. 15-keto-prostaglandin F2alpha reduction
  2. Transport of 15-Keto-Prostaglandin F2A, Lactate Antiport
  3. transport of L-lactate and retinoate (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 2 morecytosol, extracellular spaceOne of 4 routes

• arachidonoyl-CoAReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLCO1B1, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosolOne of 3 routes

• CHEBI:15519Reach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. Cholate:CoA ligase (AMP-forming)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC27A2 and 1 moreextracellular space, cytosol, endoplasmic reticulum

• (S)-malateReach from here →
  1. prostaglandin F2alpha(out) + 2 (S)-lactate(in) = prostaglandin F2alpha(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 F2alpha (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and leucine (cytosol to extracellular)

  Catalysed by SLCO2A1, SLC7A9, SLC3A1extracellular space, cytosolOne of 3 routes

• 12(S)-HPETEReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by SLCO1B1, ALOX12extracellular space, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by SLCO1B1, ALOX15B, ALOX15extracellular space, cytosolOne of 6 routes

• 5(S)-HPETEReach from here →
  1. transport of prostaglandin F2alpha (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by SLCO1B1, ALOX5extracellular space, cytosol

• (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 F2alpha (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and homoserine (cytosol to extracellular)

  Catalysed by SLCO2A1, SLC7A5extracellular space, cytosolOne of 3 routes

• formateReach from here →
  1. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by SLCO2A1, ADH1C, ADH1A, ADH5 and 4 moreextracellular space, cytosol

• malonateReach from here →
  1. prostaglandin F2alpha(out) + a dicarboxylate(in) = prostaglandin F2alpha(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 F2alpha (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and histidine (cytosol to extracellular)

  Catalysed by SLCO2A1, SLC7A6extracellular space, cytosolOne of 2 routes

• (R)-lactateReach from here →
  1. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-lactoylglutathione + H2O = (R)-lactate + glutathione + H(+)

  Catalysed by SLCO2A1, GLO1, GLOD4, HAGHextracellular space, cytosol