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

Three steps

• maleateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. maleate(in) + sulfate(out) = maleate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• malonic acidReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. transport of malonate and sulfate (cytosol to mitochondria)

  Catalysed by SULT1E1, STS, SLC25A10cytosol, mitochondrial matrixOne of 2 routes

• adipic acidReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  3. hexanedioate + glutaryl-CoA = hexanedioyl-CoA + glutarate

  Catalysed by SULT1E1, SLC22A24, SLC22A8, SUGCTcytosol, inner side of the membrane, outer side of the membrane

• (2R,3R)-tartrateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. (2R,3R)-tartrate(in) + sulfate(out) = (2R,3R)-tartrate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (S,S)-tartrateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. (S,S)-tartrate(in) + sulfate(out) = (S,S)-tartrate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3R)-citramalateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. (3R)-citramalate(in) + sulfate(out) = (3R)-citramalate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3S)-citramalateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. (3S)-citramalate(in) + sulfate(out) = (3S)-citramalate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of arachidonate (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• thiosulfateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. thiosulfate(in) + sulfate(out) = thiosulfate(out) + sulfate(in)

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30 and 2 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 16alpha,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 = 16alpha,17beta-dihydroxyandrost-4-en-3-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 6beta,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. cytochrome P450 (testosterone)

  Catalysed by HSD3B1, HSD3B2, HSD17B6, HSD17B1 and 7 moreendoplasmic reticulum, cytosolOne of 2 routes

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

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

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

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

• taurocholateReach 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, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• 5alpha-androstane-3alpha,17beta-diolReach from here →
  1. 3beta-hydroxyandrost-5-en-17-one + NADPH + H(+) = androst-5-en-3beta,17beta-diol + NADP(+)
  2. 3beta-hydroxy-Delta(5)-steroid dehydrogenase (5-alpha-dihydrotestosterone)
  3. 3beta-Hydroxysteroid:NADP+ oxidoreductase

  Catalysed by AKR1B15, HSD17B3, HSD3B1, HSD3B2 and 1 morecytosolOne of 3 routes

• glycolithocholic acidReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of glycolithocholate (cytosol to extracellular)

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

• (S)-lactic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. transport of acetate and L-lactate (cytosol to extracellular)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 moreendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by CYP17A1, ASAH1endoplasmic reticulum, cytosol

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  3. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 3-(methylsulfanyl)propanoate + CO + formate + 2 H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, ADI1endoplasmic reticulumOne of 2 routes

• 3,3',5-triiodo-L-thyronineReach 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

• 3beta-hydroxy-5alpha-androstan-17-oneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  3. 3beta-hydroxy-5alpha-androstan-17-one + NAD(+) = 5alpha-androstan-3,17-dione + NADH + H(+)

  Catalysed by HSD3B1, HSD3B2, AKR1D1, HSD17B6endoplasmic reticulum, cytosolOne of 2 routes

• butanoyl-CoAReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)
  3. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate

  Catalysed by SULT1E1, SLC22A9, ACSM1, ACSM2A and 3 morecytosol, inner side of the membrane, outer side of the membrane

• glutaryl-CoAReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  3. glutarate + succinyl-CoA = glutaryl-CoA + succinate

  Catalysed by SULT1E1, SLC22A24, SLC22A8, SUGCTcytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• propanoyl-CoAReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. propanoate(out) + dehydroepiandrosterone 3-sulfate(in) = propanoate(in) + dehydroepiandrosterone 3-sulfate(out)
  3. propanoate + ATP + CoA = propanoyl-CoA + AMP + diphosphate

  Catalysed by SULT1E1, SLC22A9, ACSM3, ACSS3 and 2 morecytosol, inner side of the membrane, outer side of the membrane

• prostaglandin E1Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin E1 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• prostaglandin I2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin I2 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• prostaglandin F2alphaReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 4 routes

• prostaglandin H2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin H2 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• prostaglandin D2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin D2 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• leukotriene A4Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of leukotriene A4 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• N-acetyl-D-glucosamine 6-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate

  Catalysed by CYP17A1, AMDHD2endoplasmic reticulum, cytosol

• S-formylglutathioneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, ESDendoplasmic reticulum

• N-sulfo-D-glucosamineReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate

  Catalysed by SULT1E1, STS, SGSHcytosol

• leukotriene C4Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of leukotriene C4 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. phosphoethanolamine + H2O = acetaldehyde + NH4(+) + phosphate

  Catalysed by CYP17A1, ETNPPLendoplasmic reticulum, cytosol

• adenosine 5'-phosphosulfateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. ATP:sulfate adenylyltransferase

  Catalysed by SULT1E1, STS, PAPSS1, PAPSS2cytosolOne of 4 routes

• N-acetylputrescineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by CYP17A1, HDAC10endoplasmic reticulum, cytosol

• taurolithocholate 3-sulfateReach 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

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

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

• L-thyroxineReach 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

• kynurenateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  3. kynurenate(out) + glutarate(in) = kynurenate(in) + glutarate(out)

  Catalysed by SULT1E1, SLC22A24, SLC22A8, SLC22A6cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N(8)-acetylspermidineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by CYP17A1, HDAC10endoplasmic reticulum, cytosol

• N-formyl-L-kynurenineReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  3. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, AFMIDendoplasmic reticulum

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by CYP17A1, ACY3endoplasmic reticulum, cytosol

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

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

• glycolithocholate 3-sulfateReach 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

• estrone 3-sulfateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. estrone 3-sulfate + H2O = estrone + sulfate + H(+)

  Catalysed by SULT1E1, STScytosolOne of 14 routes

• prostaglandin E2Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of prostaglandin E2 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• (5-hydroxyindol-3-yl)acetateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. Transport of 5-Hydroxyindoleacetate

  Catalysed by SULT1E1, STS, SLC4A1cytosol, extracellular spaceOne of 2 routes

• 2-deoxy-D-ribose 5-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde

  Catalysed by CYP17A1, DERAendoplasmic reticulum, cytosol