17alpha-hydroxyprogesterone

Three steps

• 16alpha,17beta-dihydroxyandrost-4-en-3-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17beta-dihydroxyandrost-4-en-3-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP17A1, HSD17B6, HSD17B1, HSD17B3 and 6 morecytosol

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

  Catalysed by CYP17A1, HSD17B6, HSD17B1, HSD17B3 and 6 morecytosol, endoplasmic reticulumOne of 2 routes

• D-serineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. D-serine = pyruvate + NH4(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• (R)-lactic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (R)-Lactate:NAD+ oxidoreductase

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A6 and 4 morecytosol, extracellular space

• 2-iminopropanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. 2-iminopropanoate + H2O = pyruvate + NH4(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• phosphoenolpyruvic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. pyruvate kinase (dTDP)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 4 morecytosol, extracellular space

• 13-cis-retinalReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. retinal dehydrogenase (13-cis-retinal)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 2 morecytosol, extracellular space, endoplasmic reticulum

• N-acetyl-beta-neuraminic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

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

  Catalysed by CYP17A1, ACY1cytosol

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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 CYP17A1, CYP19A1, ADI1cytosolOne of 2 routes

• 3beta-hydroxy-5alpha-androstan-17-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  3. 3beta-hydroxy-5alpha-androstan-17-one + NAD(+) = 5alpha-androstan-3,17-dione + NADH + H(+)

  Catalysed by CYP17A1, AKR1D1, HSD17B6cytosolOne of 2 routes

• 2-deoxy-alpha-D-ribose 1-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde
  3. 2-deoxy-alpha-D-ribose 1-phosphate = 2-deoxy-D-ribose 5-phosphate

  Catalysed by CYP17A1, DERA, PGM2endoplasmic reticulum

• a 3-acylpyruvateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• acetoacetyl-CoAReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A6 and 3 morecytosol, extracellular spaceOne of 2 routes

• butanoyl-CoAReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and butyrate (cytosol to extracellular)
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 7 morecytosol, extracellular spaceOne of 2 routes

• ethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. phosphoethanolamine + H2O = acetaldehyde + NH4(+) + phosphate
  3. phosphoethanolamine + H2O = ethanolamine + phosphate

  Catalysed by CYP17A1, ETNPPL, ALPL, PHOSPHO1endoplasmic reticulum

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• S-formylglutathioneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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 CYP17A1, CYP19A1, ESDcytosol

• 2-methyl-3-oxopropanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• sphing-4-enineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by CYP17A1, ASAH1cytosol

• N-acetyl-alpha-D-glucosamine 1-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
  3. N-acetyl-alpha-D-glucosamine 1-phosphate = N-acetyl-D-glucosamine 6-phosphate

  Catalysed by CYP17A1, AMDHD2, PGM3cytosol

• spermidineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N(8)-acetylspermidine + H2O = spermidine + acetate
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by CYP17A1, HDAC10cytosolOne of 2 routes

• L-methionineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 4 morecytosol, extracellular space

• a 2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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 2-acyl-sn-glycero-3-phosphocholine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• CDP-ethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. phosphoethanolamine + H2O = acetaldehyde + NH4(+) + phosphate
  3. phosphoethanolamine + CTP + H(+) = CDP-ethanolamine + diphosphate

  Catalysed by CYP17A1, ETNPPL, PCYT2endoplasmic reticulumOne of 2 routes

• L-alanineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space, mitochondrial matrixOne of 18 routes

• a 1-acyl-sn-glycero-3-phosphocholineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, PLA2G15cytosol

• cadaverineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-acetylcadaverine + H2O = cadaverine + acetate
  3. N-acetylcadaverine + H2O = cadaverine + acetate

  Catalysed by CYP17A1, HDAC10cytosol

• N-formyl-L-kynurenineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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 CYP17A1, CYP19A1, AFMIDcytosol

• (3S)-citramalyl-CoAReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• an S-substituted L-cysteineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ACY3cytosol

• D-glucosamine 6-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, AMDHD2, GNPNAT1cytosolOne of 2 routes

• 5-amino-2-oxopentanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• D-glyceraldehyde 3-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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

• estrone 3-sulfateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase

  Catalysed by CYP17A1, CYP19A1, SULT1A3, SULT1E1 and 1 morecytosol, endoplasmic reticulumOne of 3 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• a 1-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• a 1-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• a 2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• a 2-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• 2-acetamido-2-deoxy-D-glucopyranose 1-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
  3. phosphoglucomutase (N-acetylglucosamine-6-phosphate)

  Catalysed by CYP17A1, AMDHD2, PGM3cytosol

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosol

• 1-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosolOne of 4 routes

• 1-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosolOne of 3 routes

• 1-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosolOne of 3 routes

• 4-acetamidobutanalReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-acetylputrescine + H2O = putrescine + acetate
  3. N-Acetylputrescine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by CYP17A1, HDAC10, AOC2, AOC1 and 3 morecytosolOne of 2 routes

• 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  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, ASAH1, PLA2G15cytosolOne of 8 routes