17alpha-hydroxypregnenolone

Three steps

• acetoneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular spaceOne of 2 routes

• formateReach 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 + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)

  Catalysed by CYP17A1, HSD3B1, HSD3B2, CYP19A1cytosol, endoplasmic reticulum

• alpha-D-glucosamine 6-phosphateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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

• 5alpha-androstan-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. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase

  Catalysed by CYP17A1, HSD3B1, HSD3B2, AKR1D1cytosol, endoplasmic reticulumOne of 5 routes

• sulfateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase

  Catalysed by CYP17A1, SULT1E1, STScytosolOne of 3 routes

• 2-methyl-3-oxopropanoic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  2. 3beta-hydroxyandrost-5-en-17-one + NADPH + H(+) = androst-5-en-3beta,17beta-diol + NADP(+)
  3. 3beta-hydroxy-Delta(5)-steroid dehydrogenase (5-alpha-dihydrotestosterone)

  Catalysed by CYP17A1, AKR1B15, HSD17B3, HSD3B1 and 1 morecytosolOne of 3 routes

• oxaloacetateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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

• (S)-lactateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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

• 3-fumarylpyruvateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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

• 5beta-androstane-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 + NADPH + H(+) = 5beta-androstane-3,17-dione + NADP(+)

  Catalysed by CYP17A1, HSD3B1, HSD3B2, AKR1D1cytosol, endoplasmic reticulum

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

  Catalysed by CYP17A1, CES2, ESD, CES1cytosol

• estroneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  3. cytochrome P450 (4-androstene-3,17-dione)

  Catalysed by CYP17A1, HSD3B1, HSD3B2, CYP19A1cytosol, endoplasmic reticulumOne of 2 routes

• propanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. propanoate(out) + dehydroepiandrosterone 3-sulfate(in) = propanoate(in) + dehydroepiandrosterone 3-sulfate(out)

  Catalysed by CYP17A1, SULT1E1, SLC22A9cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• aceneuramateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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

• testosteroneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  3. testosterone:NADP+ 17-oxidoreductase

  Catalysed by CYP17A1, HSD3B1, HSD3B2, HSD17B6 and 7 morecytosol, endoplasmic reticulumOne of 4 routes

• cortisolReach from here →
  1. cytochrome P450
  2. 11-Deoxycortisol delta5-delat4-isomerase
  3. steroid,reduced ferredoxin:oxygen oxidoreductase (11-hydroxylating)

  Catalysed by CYP21A2, HSD3B1, HSD3B2, CYP11B1 and 1 morecytosol, mitochondrial matrixOne of 2 routes

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

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

• butanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)

  Catalysed by CYP17A1, SULT1E1, SLC22A9cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

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

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

• 3beta-hydroxy-5-androstene-7,17-dioneReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3beta-hydroxyandrost-5-en-17-one + reduced [NADPH--hemoprotein reductase] + O2 = 3beta,7alpha-dihydroxyandrost-5-en-17-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 3beta,7alpha-dihydroxyandrost-5-en-17-one + NADP(+) = 3beta-hydroxy-5-androstene-7,17-dione + NADPH + H(+)

  Catalysed by CYP17A1, CYP7B1, HSD11B1cytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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

• 19-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. 19-hydroxyandrostenedione,NADPH-hemoprotein reductase:oxygen 19-oxidoreductase

  Catalysed by CYP17A1, HSD3B1, HSD3B2, CYP19A1cytosol, endoplasmic reticulumOne of 2 routes

• 16alpha-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 = 16alpha-hydroxyandrost-4-ene-3,17-dione + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP17A1, HSD3B1, HSD3B2cytosol, endoplasmic reticulum

• 11beta-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 + 2 reduced [adrenodoxin] + O2 + 2 H(+) = 11beta-hydroxyandrost-4-ene-3,17-dione + 2 oxidized [adrenodoxin] + H2O

  Catalysed by CYP17A1, HSD3B1, HSD3B2, CYP11B1cytosol, endoplasmic reticulum

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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

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

  Catalysed by CYP17A1, DERAcytosol

• chlorine(.)Reach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by CYP17A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular spaceOne of 2 routes

• 3-hydroxypyruvic acidReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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

• glutarateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)

  Catalysed by CYP17A1, SULT1E1, SLC22A24, SLC22A8cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• pentanoateReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  2. 3'-phosphoadenylylsulfate:alcohol sulfotransferase
  3. pentanoate(out) + dehydroepiandrosterone 3-sulfate(in) = pentanoate(in) + dehydroepiandrosterone 3-sulfate(out)

  Catalysed by CYP17A1, SULT1E1, SLC22A9cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by CYP17A1, HDAC10cytosol

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

  Catalysed by CYP17A1, PON1, PON2, PON3cytosol

• D-serineReach from here →
  1. cytochrome P450 (17alpha-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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-hydroxypregnenolone)
  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