3beta-hydroxyandrost-5-en-17-one

Three steps

• (R)-noradrenalineReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of noradrenaline (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

• 16alpha,17alpha-dihydroxyprogesteroneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 17alpha-Hydroxypregnenolone:NAD+ 3-oxidoreductase
  3. 17alpha-hydroxyprogesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17alpha-dihydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP17A1, HSD3B1, HSD3B2endoplasmic reticulum

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• 16alpha-hydroxyestroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. unspecific monooxygenase (estrone)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, CYP1A1 and 22 moreendoplasmic reticulum, cytosolOne of 3 routes

• ursodeoxycholateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

• 19-oxo-androst-4-ene-3,17-dioneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. 19-hydroxyandrostenedione,NADPH-hemoprotein reductase:oxygen 19-oxidoreductase
  3. cytochrome P450 (19-hydroxyandrostenedione)

  Catalysed by HSD3B1, HSD3B2, CYP19A1endoplasmic reticulum, cytosolOne of 2 routes

• 11beta,17beta-dihydroxyandrost-4-ene-3-oneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 11beta,17beta-dihydroxyandrost-4-ene-3-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, HSD17B6, HSD17B1 and 7 moreendoplasmic reticulum, cytosolOne of 3 routes

• prostaglandin G2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin G2 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

  Catalysed by SULT1E1, SLC22A24, SLC22A8cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 16beta,17beta-dihydroxyandrost-4-en-3-oneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 16beta,17beta-dihydroxyandrost-4-en-3-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, HSD17B6, HSD17B1 and 8 moreendoplasmic reticulum, cytosol

• pentanalReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. pentanoate(out) + dehydroepiandrosterone 3-sulfate(in) = pentanoate(in) + dehydroepiandrosterone 3-sulfate(out)
  3. pentanal + NAD(+) + H2O = pentanoate + NADH + 2 H(+)

  Catalysed by SULT1E1, SLC22A9, ALDH9A1cytosol, inner side of the membrane, outer side of the membrane

• 2-hydroxytestosteroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 2-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, HSD17B6, HSD17B1 and 7 moreendoplasmic reticulum, cytosol

• 4-hydroxyestroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, CYP1A1 and 5 moreendoplasmic reticulum

• 6alpha-hydroxyestroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 6alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, CYP1A1endoplasmic reticulum

• 15alpha-hydroxyestroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 15alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, CYP1A1endoplasmic reticulum

• 3beta-hydroxy-5beta-androstane-17-oneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. androst-4-ene-3,17-dione + NADPH + H(+) = 5beta-androstane-3,17-dione + NADP(+)
  3. 5beta-androstane-3,17-dione + NADPH + H(+) = 3beta-hydroxy-5beta-androstane-17-one + NADP(+)

  Catalysed by HSD3B1, HSD3B2, AKR1D1, DHRS4endoplasmic reticulum

• thromboxane B2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• taurochenodeoxycholateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by SULT1E1, SLCO1B1, SLCO1A2, SLC7A9 and 1 morecytosol, extracellular spaceOne of 2 routes