cortisol

Three steps

• (3S)-citramalyl-CoAReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 6 morecytosol, extracellular space

• an S-substituted L-cysteineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 1 morecytosol

• D-glucosamine 6-phosphateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
  3. D-glucosamine 6-phosphate + acetyl-CoA = N-acetyl-D-glucosamine 6-phosphate + CoA + H(+)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 2 routes

• 5-amino-2-oxopentanoateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 6 morecytosol, extracellular space

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

  Catalysed by CYP17A1, DERAendoplasmic reticulum

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 6 morecytosol, extracellular space

• a 1-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. a 1,2-diacyl-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phospho-L-serine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• a 1-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphoethanolamine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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 = 1-O-acyl-N-(acetyl)-sphing-4-enine + 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• a 2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 2-acyl-sn-glycero-3-phosphoethanolamine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• a 2-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. a 1,2-diacyl-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = a 2-acyl-sn-glycero-3-phospho-L-serine + 1-O-acyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-acetamido-2-deoxy-D-glucopyranose 1-phosphateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
  3. phosphoglucomutase (N-acetylglucosamine-6-phosphate)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 6 morecytosol, extracellular space

• 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 4 routes

• 1-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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 = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 3 routes

• 1-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-octadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 3 routes

• 4-acetamidobutanalReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-acetylputrescine + H2O = putrescine + acetate
  3. N-Acetylputrescine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 6 morecytosolOne of 2 routes

• 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 8 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 2 routes

• 1-octadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 5 routes

• 2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-(9Z)-octadecenoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-octadecanoyl-sn-glycero-3-phosphocholine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-hexadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 9 routes

• 2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 2 routes

• 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 3 routes

• 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 3 routes

• 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 16alpha,17alpha-dihydroxyprogesteroneReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. 17alpha-hydroxyprogesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17alpha-dihydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2cytosol, endoplasmic reticulum

• 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosolOne of 8 routes

• N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  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, CYP11B1, CYP11B2, BCO2 and 2 morecytosol

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. steroid 11beta-monooxygenase (cortisol)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by CYP17A1, CYP11B1, CYP11B2, BCO2 and 8 morecytosol, extracellular space, mitochondrial matrix