estrone 3-sulfate

Three steps

• AReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, DIO1 and 1 moreextracellular space, cytosolOne of 7 routes

• (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP3A4 and 5 moreextracellular space, cytosol

• (14R,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (14R,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP3A4 and 5 moreextracellular space, cytosol

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

  Catalysed by SLCO1B1, CYP2C8, CYP2C9, CYP2C19 and 2 moreextracellular space, cytosol

• (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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

• S-butanoyl-4'-phosphopantetheineReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  3. butanoyl-CoA + H2O = S-butanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC22A9, ACSM1, ACSM2A, ACSM3 and 5 moreinner side of the membrane, outer side of the membrane

• 17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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

• a quinoneReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. transport of fumarate and sulfate (cytosol to mitochondria)
  3. a quinone + succinate = fumarate + a quinol

  Catalysed by STS, SLC25A10, SDHBcytosol, mitochondrial matrix

• 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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

• prostaglandin J2Reach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin J2 hydrolysis

  Catalysed by SLCO1B1extracellular space, cytosolOne of 2 routes

• 15-oxoprostaglandin F2alphaReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of prostaglandin F2alpha (cytosol to extracellular)
  3. 15-keto-prostaglandin F2alpha reduction

  Catalysed by SLCO1B1extracellular space, cytosolOne of 4 routes

• dopamine 3-O-sulfateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione

  Catalysed by SLCO1B1, GSTA1, GSTM1extracellular space, cytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. transport of estrone 3-sulfate (cytosol to extracellular)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione

  Catalysed by SLCO1B1, GSTP1, GSTM1extracellular space, cytosol

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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

• 17beta-estradiol 3-sulfateReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. 17beta-estradiol + 3'-phosphoadenylyl sulfate = 17beta-estradiol 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by STS, HSD17B6, HSD17B1, HSD17B2 and 7 morecytosol

• 16alpha-hydroxyestrone 3-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. unspecific monooxygenase (estrone)
  3. 16alpha-hydroxyestrone + UDP-alpha-D-glucuronate = 16alpha-hydroxyestrone 3-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, CYP1A1, CYP1A2, CYP2E1 and 22 morecytosol

• 16alpha-hydroxyestrone 16-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. unspecific monooxygenase (estrone)
  3. 16alpha-hydroxyestrone + UDP-alpha-D-glucuronate = 16alpha-hydroxyestrone 16-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, CYP1A1, CYP1A2, CYP2E1 and 22 morecytosol

• 17beta-estradiol 3-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. UDPglucuronate beta-D-glucuronosyltransferase(acceptor-unspecific)

  Catalysed by STS, HSD17B6, HSD17B1, HSD17B2 and 24 morecytosol, endoplasmic reticulumOne of 2 routes

• 17alpha-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. 17alpha-estradiol + NADP(+) = estrone + NADPH + H(+)
  3. 17alpha-estradiol + UDP-alpha-D-glucuronate = 17alpha-estradiol 17-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, DHRS1, UGT2B17, UGT2B4 and 2 morecytosol

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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

• 2-hydroxyestrone 3-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. cytochrome P450 (estrone)
  3. 2-hydroxyestrone + UDP-alpha-D-glucuronate = 2-hydroxyestrone 3-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, CYP3A4, UGT1A9, UGT1A1 and 1 morecytosol

• 4-hydroxyestrone 3-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 4-hydroxyestrone + UDP-alpha-D-glucuronate = 4-hydroxyestrone 3-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, CYP1A1, CYP1A2, CYP3A4 and 4 morecytosol

• estrone 4-O-(beta-D-glucuronate)Reach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 4-hydroxyestrone + UDP-alpha-D-glucuronate = estrone 4-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by STS, CYP1A1, CYP1A2, CYP3A4 and 6 morecytosol

• 4-methoxyestroneReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 4-hydroxyestrone + S-adenosyl-L-methionine = 4-methoxyestrone + S-adenosyl-L-homocysteine + H(+)

  Catalysed by STS, CYP1A1, CYP1A2, CYP3A4 and 4 morecytosol

• 2-hydroxy-3-methoxy-estroneReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. cytochrome P450 (estrone)
  3. 2-hydroxyestrone + S-adenosyl-L-methionine = 2-hydroxy-3-methoxy-estrone + S-adenosyl-L-homocysteine + H(+)

  Catalysed by STS, CYP3A4, COMTcytosol

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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

• beta-D-glucosyl-(1->3)-O-chenodeoxycholateReach from here →
  1. transport of estrone 3-sulfate (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

• indoxyl sulfateReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. indoxyl sulfate(out) + a dicarboxylate(in) = indoxyl sulfate(in) + a dicarboxylate(out)

  Catalysed by STS, SLC25A35, SLC25A34, SLC22A6 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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 estrone 3-sulfate (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. Estrone 3-sulfate sulfohydrolase
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. transport of chloride and choline (cytosol to extracellular)

  Catalysed by STS, SLC26A6, SLC5A7cytosol, extracellular spaceOne of 6 routes

• pyruvateReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. transport of malate and sulfate (cytosol to mitochondria)
  3. (S)-malate:NAD+ oxidoreductase (decarboxylating)

  Catalysed by STS, SLC25A10, ME2, ME3cytosol, mitochondrial matrixOne of 7 routes

• arachidonoyl-CoAReach from here →
  1. transport of estrone 3-sulfate (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 estrone 3-sulfate (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

• L-leucineReach from here →
  1. Estrone 3-sulfate sulfohydrolase
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. transport of chloride and leucine (cytosol to extracellular)

  Catalysed by STS, SLC26A6, SLC6A14cytosol, extracellular spaceOne of 4 routes

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

  Catalysed by SLCO1B1, ALOX15B, ALOX15extracellular space, cytosolOne of 4 routes