17alpha-hydroxyprogesterone

Three steps

• 2beta-hydroxytestosteroneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 2beta-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 25 morecytosol, extracellular spaceOne of 2 routes

• 17beta-hydroxy-androst-5-en-3-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. 17beta-hydroxy-androst-5-en-3-one = testosterone

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

• 2-(9Z-octadecenoyl)-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 = 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-octadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• 2-nonadioyl-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-nonadioyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-nonadioyl-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by CYP17A1, ASAH1, PLA2G15cytosol

• CHEBI:15345Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. Acetoacetate:CoA ligase (AMP-forming)

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

• acetoneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. Acetoacetate carboxy-lyase (acetone-forming)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A6 and 2 morecytosol, extracellular space, mitochondrial matrix

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

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 4 morecytosol, extracellular spaceOne of 3 routes

• (S)-malateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• 10-formyltetrahydrofolic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by CYP17A1, CYP19A1, MTHFD1cytosol, endoplasmic reticulumOne of 2 routes

• alpha-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. N-Acetyl-D-glucosamine-6-phosphate amidohydrolase

  Catalysed by CYP17A1, AMDHD2, CEMP1cytosol

• androsteroneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  3. Androsterone:NAD+ oxidoreductase

  Catalysed by CYP17A1, AKR1D1, AKR1C4, AKR1C3 and 2 morecytosolOne of 6 routes

• 2-methyl-3-oxopropanoic acidReach 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 matrix

• 17beta-hydroxy-5alpha-androstan-3-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. dihydrotestosterone:NADP+ delta4-oxidoreductase

  Catalysed by CYP17A1, HSD17B6, HSD17B1, HSD17B3 and 8 morecytosolOne of 4 routes

• oxaloacetateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. Pyruvate:carbon-dioxide ligase (ADP-forming)

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

• 17beta-estradiolReach 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 7 routes

• (S)-lactateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 7 morecytosol, extracellular space

• 2-oxobutanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of 2-hydroxybutyrate and acetate (cytosol to extracellular)
  3. 2-hydroxybutyrate:NAD+ oxidoreductase

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7 and 5 morecytosol, extracellular spaceOne of 2 routes

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

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• formaldehydeReach 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. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)

  Catalysed by CYP17A1, CYP19A1, ALDH9A1cytosol

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

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

• ferrocytochrome cReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and L-lactate (cytosol to extracellular)
  3. (S)-Lactate:ferricytochrome-c 2-oxidoreductase

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

• cortisoneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. steroid,reduced ferredoxin:oxygen oxidoreductase (11-hydroxylating)
  3. Cortisol:NADP+ 11-oxidoreductase

  Catalysed by CYP21A2, CYP11B1, CYP11B2, HSD11B1cytosol, mitochondrial matrixOne of 5 routes

• 17alpha-estradiolReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. 17alpha-estradiol + NADP(+) = estrone + NADPH + H(+)

  Catalysed by CYP17A1, CYP19A1, DHRS1cytosol, endoplasmic reticulum

• 3-hydroxypyruvateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. L-serine + pyruvate = 3-hydroxypyruvate + L-alanine

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

• 4-methylumbelliferoneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)
  3. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

  Catalysed by CYP17A1, CES2, ESD, CES1cytosol

• aceneuramateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. aceneuramate = aldehydo-N-acetyl-D-mannosamine + pyruvate

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

• 5'-deoxyadenosineReach 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

• urateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and L-lactate (cytosol to extracellular)
  3. transport of L-lactate and urate (cytosol to extracellular)

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

• all-trans-retinalReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. retinoate reduction

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A7cytosol, extracellular space

• 4-fumarylacetoacetateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A6 and 3 morecytosol, extracellular space

• dTDPReach 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

• testosterone 17-sulfateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. sulfotransferase (PAPS)

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

• (6R)-10-formyltetrahydrofolateReach 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. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate

  Catalysed by CYP17A1, CYP19A1, MTHFD1, MTHFD1Lcytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

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

• 5-(3,3'-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

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

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

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

• 5beta-dihydrotestosteroneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. testosterone:NADP+ 17-oxidoreductase
  3. 5beta-dihydrotestosterone + NADP(+) = testosterone + NADPH + H(+)

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

• androst-4-ene-3,11,17-trioneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. androst-4-ene-3,17-dione + 2 reduced [adrenodoxin] + O2 + 2 H(+) = 11beta-hydroxyandrost-4-ene-3,17-dione + 2 oxidized [adrenodoxin] + H2O
  3. 11beta-hydroxyandrost-4-ene-3,17-dione + NAD(+) = androst-4-ene-3,11,17-trione + NADH + H(+)

  Catalysed by CYP17A1, CYP11B1, HSD11B2cytosolOne of 2 routes

• 17alpha,21-dihydroxypregnenoloneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. cytochrome P450

  Catalysed by CYP17A1, CYP21A2cytosol, endoplasmic reticulum

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach 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 3 routes

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by CYP17A1cytosol, endoplasmic reticulumOne of 6 routes

• CHEBI:29052Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. deoxyribose-phosphate aldolase
  3. deoxyribose-phosphate aldolase

  Catalysed by CYP17A1, DERAendoplasmic reticulum, cytosol

• chlorine(.)Reach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (4-androstene-3,17-dione)
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by CYP17A1, CYP19A1, SLC26A4cytosol, endoplasmic reticulum, extracellular spaceOne of 2 routes

• oxalateReach 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. oxalate(in) + formate(out) = oxalate(out) + formate(in)

  Catalysed by CYP17A1, CYP19A1, SLC26A6cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 3-hydroxypyruvic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. L-Serine:pyruvate aminotransferase

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• putrescineReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. N-acetylputrescine + H2O = putrescine + acetate
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by CYP17A1, HDAC10cytosol

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

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

• a phenolReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. a phenyl acetate + H2O = a phenol + acetate + H(+)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by CYP17A1, PON1, PON2, PON3cytosol