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

Three steps

• 2beta-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 = 2beta-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• a phenyl acetateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by CYP17A1, PON1, PON2, PON3endoplasmic reticulum, cytosol

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

  Catalysed by SULT1E1, STS, ARSL, ARSF and 4 morecytosol

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

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

• acetylpyruvateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by CYP17A1, FAHD1endoplasmic reticulum, cytosol

• pyruvateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. transport of acetate and pyruvate (cytosol to extracellular)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 2 moreendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• all-trans-retinoic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. transport of acetate and retinoate (cytosol to extracellular)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7endoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

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

  Catalysed by SULT1E1, STS, SLC25A10cytosol, mitochondrial matrixOne of 4 routes

• 10-formyltetrahydrofolic acidReach 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. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, MTHFD1endoplasmic reticulum, cytosolOne of 2 routes

• CHEBI:15650Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

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

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

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

  Catalysed by SULT1E1, STS, SLC25A14, SLC25A30 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• androsteroneReach 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. Androsterone:NAD+ oxidoreductase

  Catalysed by HSD3B1, HSD3B2, AKR1D1, AKR1C4 and 3 moreendoplasmic reticulum, cytosolOne of 6 routes

• CHEBI:16132Reach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. deoxyribose-phosphate aldolase

  Catalysed by CYP17A1, DERAendoplasmic reticulum, cytosol

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

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

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

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

• (17R,20S)-17,20-dihydroxypregn-4-en-3-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 17alpha-Hydroxypregnenolone:NAD+ 3-oxidoreductase
  3. (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD(+) = 17alpha-hydroxyprogesterone + NADH + H(+)

  Catalysed by CYP17A1, HSD3B1, HSD3B2, AKR1C1endoplasmic reticulumOne of 2 routes

• 17beta-estradiolReach 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 7 routes

• N(2)-acetyl-L-ornithineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. N2-Acetyl-L-ornithine amidohydrolase

  Catalysed by CYP17A1, ACY1endoplasmic reticulum, cytosol

• quinolinic acidReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. Transport of Quinolinic Acid

  Catalysed by SULT1E1, STS, SLC22A6cytosol, extracellular spaceOne of 2 routes

• formaldehydeReach 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. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, ALDH9A1endoplasmic reticulum

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

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

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

  Catalysed by SULT1E1, STS, SLC26A6cytosol, extracellular space

• (R)-3-hydroxybutyric acidReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. transport of (R)-3-hydroxybutanoate and acetate (cytosol to extracellular)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 1 moreendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• 17alpha-estradiolReach 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. 17alpha-estradiol + NADP(+) = estrone + NADPH + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP19A1, DHRS1endoplasmic reticulum

• taurolithocholateReach 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

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

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

• 3-hydroxy-3-methylglutarateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  3. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate

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

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

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

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. Steryl-Sulfatase

  Catalysed by SULT1E1, STScytosol, Golgi apparatusOne of 2 routes

• 4-methylumbelliferyl acetateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

  Catalysed by CYP17A1, CES2, ESD, CES1endoplasmic reticulum, cytosol

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

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

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

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

• testosterone 17-sulfateReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. testosterone:NADP+ 17-oxidoreductase
  3. sulfotransferase (PAPS)

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

• 5alpha-androstane-3alpha,17beta-diol 3-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. 5alpha-androstane-3alpha,17beta-diol 3-O-(beta-D-glucuronate)(out) + glutarate(in) = 5alpha-androstane-3alpha,17beta-diol 3-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

• (6R)-10-formyltetrahydrofolateReach 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. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate

  Catalysed by HSD3B1, HSD3B2, CYP19A1, MTHFD1 and 1 moreendoplasmic reticulum

• 5beta-dihydrotestosteroneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. testosterone:NADP+ 17-oxidoreductase
  3. 5beta-dihydrotestosterone + NADP(+) = testosterone + NADPH + H(+)

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

• androst-4-ene-3,11,17-trioneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  2. androst-4-ene-3,17-dione + 2 reduced [adrenodoxin] + O2 + 2 H(+) = 11beta-hydroxyandrost-4-ene-3,17-dione + 2 oxidized [adrenodoxin] + H2O
  3. 11beta-hydroxyandrost-4-ene-3,17-dione + NAD(+) = androst-4-ene-3,11,17-trione + NADH + H(+)

  Catalysed by HSD3B1, HSD3B2, CYP11B1, HSD11B2endoplasmic reticulumOne of 2 routes

• folic acidReach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. Folate Transport by Oats

  Catalysed by SULT1E1, STS, SLC22A8, SLC22A7cytosol, extracellular spaceOne of 2 routes

• 11-deoxycortisolReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. cytochrome P450
  3. 11-Deoxycortisol delta5-delat4-isomerase

  Catalysed by CYP17A1, CYP21A2, HSD3B1, HSD3B2endoplasmic reticulum, cytosolOne of 4 routes

• CHEBI:28666Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. transport of LTD4 (cytosol to extracellular)

  Catalysed by SULT1E1, SLCO1B1cytosol, extracellular spaceOne of 2 routes

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

  Catalysed by SULT1E1, STS, SLC25A35, SLC25A34cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• chlorine(.)Reach from here →
  1. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. transport of chloride and sulfate (cytosol to extracellular)

  Catalysed by SULT1E1, STS, SLC26A6cytosol, extracellular spaceOne of 3 routes

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

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

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

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

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

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

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

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

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

  Catalysed by SULT1E1, STS, SLC25A14, SLC26A2 and 3 morecytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

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

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 1 moreendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

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

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 1 moreendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes