17alpha-hydroxypregnenolone

Three steps

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-O-acyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phosphoserine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosolOne of 8 routes

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

  Catalysed by CYP17A1, ASAH1, CERKcytosol

• androst-5-en-3beta,7alpha,17beta-triolReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3beta-hydroxyandrost-5-en-17-one + NADPH + H(+) = androst-5-en-3beta,17beta-diol + NADP(+)
  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 CYP17A1, AKR1B15, HSD17B3, CYP7B1cytosol

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP17A1, SULT1E1, CYP3A7cytosol

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

  Catalysed by CYP17A1, HSD3B1, HSD3B2, CYP3A4 and 1 morecytosol, endoplasmic reticulum

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 5 morecytosol, extracellular space, mitochondrial matrix