19-oxo-androst-4-ene-3,17-dione

Three steps

• L-phenylalanineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Phenylalanine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• N-acetylputrescineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular space

• 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 H(+)
  2. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate
  3. (6R)-10-formyltetrahydrofolate + 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + (6S)-5,6,7,8-tetrahydrofolate

  Catalysed by CYP19A1, MTHFD1, MTHFD1L, ATIC

• N(8)-acetylspermidineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular space

• (3S)-citramalyl-CoAReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular space

• 5-amino-2-oxopentanoateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space

• 5-methylsulfanyl-2,3-dioxopentyl phosphateReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 H(+)
  2. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 3-(methylsulfanyl)propanoate + CO + formate + 2 H(+)
  3. 5-methylsulfanyl-2,3-dioxopentyl phosphate + H2O = 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + phosphate

  Catalysed by CYP19A1, ADI1, ENOPH1

• 4-aminobutanoateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A12cytosol, extracellular spaceOne of 4 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space

• 4-hydroxy-17beta-estradiolReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. cytochrome P450 (estradiol-17beta)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 5 morecytosolOne of 3 routes

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. 17beta-estradiol + UDP-alpha-D-glucuronate = 17beta-estradiol 17-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 9 morecytosol

• 16beta,17beta-estriolReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. 17beta-estradiol + reduced [NADPH--hemoprotein reductase] + O2 = 16beta,17beta-estriol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 5 morecytosol

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 5 morecytosol, extracellular space, mitochondrial matrix