androst-4-ene-3,17-dione

Three steps

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

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

• oxaloacetateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. Pyruvate:carbon-dioxide ligase (ADP-forming)

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

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

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

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

  Catalysed by CYP17A1, ACY1endoplasmic reticulum, cytosol

• (S)-lactateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 7 moreendoplasmic reticulum, extracellular space, cytosol

• 4-methylsulfanyl-2-oxobutanoateReach 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 = 4-methylsulfanyl-2-oxobutanoate + formate + 2 H(+)

  Catalysed by CYP19A1, ADI1

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

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 5 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

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

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

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

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

• CHEBI:16856Reach 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 hydrolase

  Catalysed by CYP19A1, ESDcytosolOne of 2 routes

• CHEBI:16857Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Threonine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosol

• ferrocytochrome cReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and L-lactate (cytosol to extracellular)
  3. (S)-Lactate:ferricytochrome-c 2-oxidoreductase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A3 and 4 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrix

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

  Catalysed by CYP19A1, SLC26A4, SLC26A6endoplasmic reticulum, extracellular space, cytosol

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

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

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

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

• CHEBI:17203Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Proline by the Apical Imino Amino Acid Transporters

  Catalysed by CYP19A1, SLC26A4, CLTRN, SLC6A20endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• COReach 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 dioxygenase

  Catalysed by CYP19A1, ADI1cytosolOne of 2 routes

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

• aceneuramateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. aceneuramate = aldehydo-N-acetyl-D-mannosamine + pyruvate

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

• 5'-deoxyadenosineReach 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, cytosol

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

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

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

  Catalysed by CYP17A1, CYP21A2, CYP11B1, CYP11B2endoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• CHEBI:17724Reach 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. dimethylglycine dehydrogenase (formaldehyde)

  Catalysed by CYP19A1, ALDH9A1, PDPR, DMGDHcytosol

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

  Catalysed by CYP19A1, SLC26A4, SLC6A12endoplasmic reticulum, extracellular space, cytosolOne of 3 routes

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

  Catalysed by CYP17A1, CES2, ESD, CES1endoplasmic reticulum, cytosol

• urateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and L-lactate (cytosol to extracellular)
  3. transport of L-lactate and urate (cytosol to extracellular)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A3 and 4 moreendoplasmic reticulum, extracellular space, cytosol

• estrone 3-O-(3-sulfo-beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. UDPglucuronate beta-D-glucuronosyltransferase(acceptor-unspecific)
  3. estrone 3-O-(beta-D-glucuronate) + 3'-phosphoadenylyl sulfate = estrone 3-O-(3-sulfo-beta-D-glucuronate) + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by CYP19A1, UGT1A1, UGT1A10, UGT1A8 and 1 moreendoplasmic reticulum

• testosterone 17-O-(3-sulfo-beta-D-glucuronate)Reach from here →
  1. testosterone:NADP+ 17-oxidoreductase
  2. 17beta-hydroxysteroid UDP-glucuronosyltransferase
  3. testosterone 17-O-(beta-D-glucuronate) + 3'-phosphoadenylyl sulfate = testosterone 17-O-(3-sulfo-beta-D-glucuronate) + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 11 morecytosol, endoplasmic reticulum

• CHEBI:17895Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Tyrosine by Atb0 Transporter

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

• all-trans-retinalReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. retinoate reduction

  Catalysed by CYP19A1, SLC16A4, SLC16A5endoplasmic reticulum, extracellular space, cytosol

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

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

• CHEBI:18019Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and lysine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosol

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

  Catalysed by CYP19A1, SLC16A4, SLC16A5, FAHendoplasmic reticulum, extracellular space, cytosol

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

  Catalysed by CYP19A1, SLC26A4, SLC6A14endoplasmic reticulum, extracellular space, cytosol

• dTDPReach 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

• CHEBI:18095Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of trans-4-hydroxy-L-proline (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, CLTRN, SLC6A20endoplasmic reticulum, extracellular space, cytosol

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

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

• N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:5'-phosphoribosylglycinamide formyltransferase

  Catalysed by CYP19A1, MTHFD1, GARTendoplasmic reticulum, cytosol

• CHEBI:18381Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by CYP19A1, MTHFD1, ATICendoplasmic reticulum, cytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

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

• 5-(3,3'-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

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

• 5-(3-methylguanidino)-2-oxopentanoateReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine

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

• (6R)-5,10-methylenetetrahydrofolic 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. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)
  3. formaldehyde to 5,10-methylene-THF conversion

  Catalysed by CYP19A1, ALDH9A1cytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:NADP+ oxidoreductase

  Catalysed by CYP19A1, MTHFD1, ALDH1L1, ALDH1L2endoplasmic reticulum, cytosolOne of 4 routes

• CHEBI:240943Reach from here →
  1. cytochrome P450 (4-androstene-3,17-dione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. 2-Methylbutyrylglycine Transport, Extracellular

  Catalysed by CYP19A1, SLC26A4, SLC6A5endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

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

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

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

  Catalysed by CYP19A1, SLC26A4, SLC12A2, SLC12A1endoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• androst-5-en-3beta,17beta-diolReach from here →
  1. testosterone:NADP+ 17-oxidoreductase
  2. dihydrotestosterone:NADP+ delta4-oxidoreductase
  3. 3beta-hydroxy-Delta(5)-steroid dehydrogenase (5-alpha-dihydrotestosterone)

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 9 morecytosolOne of 4 routes

• 3beta,16alpha-dihydroxy-androst-5-en-17-oneReach from here →
  1. 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
  2. Androsterone:NAD+ oxidoreductase
  3. hydroxysteroid 17-beta dehydrogenase (androsterone)

  Catalysed by AKR1D1, AKR1C4, AKR1C3, AKR1C2 and 2 morecytosol, endoplasmic reticulum

• 16alpha,17beta-estriolReach from here →
  1. testosterone:NADP+ 17-oxidoreductase
  2. cytochrome P450 (testosterone)
  3. ESTRr

  Catalysed by HSD17B6, HSD17B1, HSD17B3, HSD17B2 and 5 morecytosol, endoplasmic reticulumOne of 3 routes