5alpha-androstan-3,17-dione

Three steps

• 6beta,17beta-dihydroxyandrost-4-en-3-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. testosterone:NADP+ 17-oxidoreductase
  3. cytochrome P450 (testosterone)

  Catalysed by AKR1D1, HSD17B6, HSD17B1, HSD17B3 and 6 morecytosol, endoplasmic reticulumOne of 2 routes

• (S)-lactic acidReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. transport of formate and L-lactate (cytosol to extracellular)

  Catalysed by AKR1D1, CYP19A1, SLC16A4, SLC16A5 and 4 morecytosol, endoplasmic reticulum, extracellular spaceOne of 2 routes

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, ADI1cytosolOne of 2 routes

• S-formylglutathioneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, ESDcytosol

• N-formyl-L-kynurenineReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, AFMIDcytosol

• estrone 3-sulfateReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase

  Catalysed by AKR1D1, CYP19A1, SULT1A3, SULT1E1 and 1 morecytosol, endoplasmic reticulumOne of 3 routes

• 16alpha,17alpha-dihydroxyprogesteroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. 17alpha-hydroxyprogesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17alpha-dihydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AKR1D1, CYP17A1cytosol, endoplasmic reticulum

• 16alpha-hydroxyestroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. unspecific monooxygenase (estrone)

  Catalysed by AKR1D1, CYP19A1, CYP1A1, CYP1A2 and 21 morecytosol, endoplasmic reticulumOne of 3 routes

• 19-oxo-androst-4-ene-3,17-dioneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. 19-hydroxyandrostenedione,NADPH-hemoprotein reductase:oxygen 19-oxidoreductase
  3. cytochrome P450 (19-hydroxyandrostenedione)

  Catalysed by AKR1D1, CYP19A1cytosolOne of 2 routes

• 11beta,17beta-dihydroxyandrost-4-ene-3-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, HSD17B6, HSD17B1, HSD17B3 and 6 morecytosolOne of 3 routes

• 16beta,17beta-dihydroxyandrost-4-en-3-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, HSD17B6, HSD17B1, HSD17B3 and 7 morecytosol

• androst-5-en-3beta,7alpha,17beta-triolReach from here →
  1. 17beta-hydroxy-5alpha-androstan-3-one + NADP(+) = 5alpha-androstan-3,17-dione + NADPH + H(+)
  2. 3beta-hydroxy-Delta(5)-steroid dehydrogenase (5-alpha-dihydrotestosterone)
  3. androst-5-en-3beta,17beta-diol + reduced [NADPH--hemoprotein reductase] + O2 = androst-5-en-3beta,7alpha,17beta-triol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AKR1B15, HSD17B3, AKR1C1, HSD3B1 and 2 morecytosol

• 2-hydroxytestosteroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 2-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AKR1D1, HSD17B6, HSD17B1, HSD17B3 and 6 morecytosol

• 4-hydroxyestroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, CYP1A1, CYP1A2 and 4 morecytosol, endoplasmic reticulum

• 6alpha-hydroxyestroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, CYP1A1cytosol, endoplasmic reticulum

• 15alpha-hydroxyestroneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, CYP19A1, CYP1A1cytosol, endoplasmic reticulum

• 3beta-hydroxy-5beta-androstane-17-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  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 AKR1D1, DHRS4cytosol