androst-4-ene-3,17-dione

Three steps

• 2-hydroxy-17beta-estradiolReach from here →
  1. testosterone:NADP+ 17-oxidoreductase
  2. cytochrome P450 (testosterone)
  3. unspecific monooxygenase (estradiol-17beta)

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 29 morecytosol, endoplasmic reticulumOne of 3 routes

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

  Catalysed by CYP17A1endoplasmic reticulum, cytosol

• malonic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Malonate Transport, Antiport with Chloride

  Catalysed by CYP19A1, SLC26A4endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• 3-hydroxypyruvic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. L-Serine:pyruvate aminotransferase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• glutarateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase
  3. estrone 3-sulfate(out) + glutarate(in) = estrone 3-sulfate(in) + glutarate(out)

  Catalysed by CYP19A1, SULT1A3, SULT1E1, SULT1A1 and 3 moreendoplasmic reticulum, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• pentanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase
  3. pentanoate(in) + estrone 3-sulfate(out) = pentanoate(out) + estrone 3-sulfate(in)

  Catalysed by CYP19A1, SULT1A3, SULT1E1, SULT1A1 and 1 moreendoplasmic reticulum, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 3-oxopropanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. 3-oxopropanoate + L-alanine = beta-alanine + pyruvate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  2. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 3-(methylsulfanyl)propanoate + CO + formate + 2 H(+)
  3. Acireductone Dixoygenase 1

  Catalysed by CYP19A1, ADI1cytosol

• D-serineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. D-serine = pyruvate + NH4(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• 5alpha-androstane-3alpha,17beta-diolReach from here →
  1. testosterone:NADP+ 17-oxidoreductase
  2. dihydrotestosterone:NADP+ delta4-oxidoreductase
  3. 3beta-Hydroxysteroid:NADP+ oxidoreductase

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 8 morecytosolOne of 5 routes

• (R)-lactic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (R)-Lactate:NAD+ oxidoreductase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by CYP19A1, SLC16A4, SLC16A5, HMGCL and 1 moreendoplasmic reticulum, extracellular space, cytosol

• 2-iminopropanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. 2-iminopropanoate + H2O = pyruvate + NH4(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• phosphoenolpyruvic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. pyruvate kinase (dTDP)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 4 moreendoplasmic reticulum, extracellular space, cytosol

• 13-cis-retinalReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. retinal dehydrogenase (13-cis-retinal)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, ALDH1A2 and 1 moreendoplasmic reticulum, extracellular space, cytosol

• N-acetyl-beta-neuraminic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

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

  Catalysed by CYP17A1, ASAH1endoplasmic reticulum, cytosol

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

  Catalysed by CYP19A1, ADI1

• taurineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Neurotransmitter:Sodium Symporter (Nss) Tcdb:2.A.22.3.3

  Catalysed by CYP19A1, SLC26A4, SLC6A6endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• a 3-acylpyruvateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• acetoacetyl-CoAReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate

  Catalysed by CYP19A1, SLC16A4, SLC16A5, AACSendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

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

  Catalysed by CYP19A1, SLC26A4, SLC6A9, SLC6A14endoplasmic reticulum, extracellular space, cytosolOne of 3 routes

• butanoyl-CoAReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of butyrate and formate (cytosol to extracellular)
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, ACSM4 and 5 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• sarcosineReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  2. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)
  3. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by CYP19A1, ALDH9A1, PIPOX

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  2. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate
  3. (6R)-10-formyltetrahydrofolate + NADP(+) + H2O = (6S)-5,6,7,8-tetrahydrofolate + CO2 + NADPH + H(+)

  Catalysed by CYP19A1, MTHFD1, MTHFD1L, ALDH1L1 and 1 moreOne of 4 routes

• (6R)-5,10-methenyltetrahydrofolateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. 5,10-Methenyltetrahydrofolate 5-hydrolase (decyclizing)

  Catalysed by CYP19A1, MTHFD1endoplasmic reticulum, cytosolOne of 3 routes

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

  Catalysed by CYP17A1, AMDHD2endoplasmic reticulum, cytosol

• 17alpha-estradiol 3-O-(beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. 17alpha-estradiol + NADP(+) = estrone + NADPH + H(+)
  3. 17alpha-estradiol + UDP-alpha-D-glucuronate = 17alpha-estradiol 3-O-(beta-D-glucuronate) + UDP + H(+)

  Catalysed by CYP19A1, DHRS1, UGT2B17, UGT2A1 and 7 moreendoplasmic reticulum

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• 2-methyl-3-oxopropanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• guanidinoacetateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of Guanidinoacetic Acid

  Catalysed by CYP19A1, SLC26A4endoplasmic reticulum, extracellular space, cytosol

• L-methionineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate 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 CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 4 moreendoplasmic reticulum, extracellular space, cytosolOne of 3 routes

• L-tryptophanReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Tryptophan by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosolOne of 3 routes

• glutathioneReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  2. S-formylglutathione + H2O = formate + glutathione + H(+)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by CYP19A1, ESD

• L-kynurenineReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
  2. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  3. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)

  Catalysed by CYP19A1, AFMID

• beta-alanineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of beta-alanine and chloride (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A6, SLC6A14endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• L-alanineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrixOne of 20 routes

• L-asparagineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Asparagine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• L-phenylalanineReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Phenylalanine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

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

  Catalysed by CYP17A1, ETNPPLendoplasmic reticulum

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

  Catalysed by CYP17A1, HDAC10endoplasmic reticulum, cytosol

• 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 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 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by CYP17A1, HDAC10endoplasmic reticulum, cytosol

• (3S)-citramalyl-CoAReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 moreendoplasmic reticulum, extracellular space, cytosol

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. cytochrome P450 (17alpha-hydroxyprogesterone)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by CYP17A1, ACY3endoplasmic reticulum, cytosol

• 5-amino-2-oxopentanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  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 moreendoplasmic reticulum, extracellular space, cytosol

• 5-methylsulfanyl-2,3-dioxopentyl phosphateReach from here →
  1. androst-4-ene-3,17-dione + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = estrone + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 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 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A12endoplasmic reticulum, extracellular space, cytosolOne of 4 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  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 moreendoplasmic reticulum, extracellular space, cytosol

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

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 6 morecytosol, endoplasmic reticulumOne of 3 routes