19-oxo-androst-4-ene-3,17-dione

Three steps

• all-trans-18-hydroxyretinoateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, CYP1A1 and 24 morecytosol, extracellular spaceOne of 2 routes

• a phenyl acetateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 3 morecytosol, extracellular space

• 3-(methylthio)propionic acidReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 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, ADI1cytosol

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 H(+)
  2. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate
  3. N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6R)-10-formyltetrahydrofolate = N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6S)-5,6,7,8-tetrahydrofolate + H(+)

  Catalysed by CYP19A1, MTHFD1, MTHFD1L, GART

• CHEBI:15345Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, AACScytosol, extracellular spaceOne of 3 routes

• acetoneReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. Acetoacetate carboxy-lyase (acetone-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5cytosol, extracellular space, mitochondrial matrix

• cholineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and choline (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC5A7cytosol, extracellular space

• acetylpyruvateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular spaceOne of 2 routes

• propionyl-CoAReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and propanoate (cytosol to extracellular)
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 3 morecytosol, extracellular spaceOne of 3 routes

• (S)-malateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular spaceOne of 2 routes

• L-leucineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and leucine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• CHEBI:15971Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and histidine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular space

• methanethiolReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 H(+)
  2. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)
  3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by CYP19A1, ALDH9A1, SELENBP1

• sulfateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase
  3. Estrone 3-sulfate sulfohydrolase

  Catalysed by CYP19A1, SULT1A3, SULT1E1, SULT1A1 and 1 morecytosolOne of 6 routes

• 2-methyl-3-oxopropanoic acidReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space, mitochondrial matrix

• iodideReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and iodide (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4cytosol, extracellular space

• L-valineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and valine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• oxaloacetateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. Pyruvate:carbon-dioxide ligase (ADP-forming)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space, mitochondrial matrixOne of 3 routes

• L-arginineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of arginine and chloride (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• N(2)-acetyl-L-ornithineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N2-Acetyl-L-ornithine amidohydrolase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular space

• (S)-lactateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 7 morecytosol, extracellular space

• 4-methylsulfanyl-2-oxobutanoateReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 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 (19-oxoandrostenedione)
  2. transport of 2-hydroxybutyrate and formate (cytosol to extracellular)
  3. 2-hydroxybutyrate:NAD+ oxidoreductase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 5 morecytosol, extracellular spaceOne of 2 routes

• 2-oxoglutaramateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. L-Glutamine:pyruvate aminotransferase

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular spaceOne of 2 routes

• 3-fumarylpyruvateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. 3-fumarylpyruvate + H2O = fumarate + pyruvate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 3 morecytosol, extracellular space

• CHEBI:16856Reach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 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 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Threonine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular space

• ferrocytochrome cReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space, mitochondrial matrix

• oxalic acidReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and oxalate (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC26A6cytosol, extracellular space

• 3-hydroxypyruvateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space

• L-isoleucineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and isoleucine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• CHEBI:17203Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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, SLC6A20cytosol, extracellular spaceOne of 2 routes

• COReach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 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

• 17alpha-hydroxyprogesteroneReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 morecytosol, extracellular space, endoplasmic reticulum

• propanoateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• aceneuramateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space

• 5'-deoxyadenosineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space

• L-cysteineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and cysteine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• CHEBI:17724Reach from here →
  1. 19-oxo-androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = estrone + formate + oxidized [NADPH--hemoprotein reductase] + H2O + 2 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 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of betaine and chloride (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A12cytosol, extracellular spaceOne of 3 routes

• 4-methylumbelliferyl acetateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetate and formate (cytosol to extracellular)
  3. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 3 morecytosol, extracellular space

• urateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, extracellular space

• estrone 3-O-(3-sulfo-beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, endoplasmic reticulum

• CHEBI:17895Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Tyrosine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular spaceOne of 2 routes

• all-trans-retinalReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. retinoate reduction

  Catalysed by CYP19A1, SLC16A4, SLC16A5cytosol, extracellular space

• butanoateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  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 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:18019Reach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride and lysine (cytosol to extracellular)

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular space

• 4-fumarylacetoacetateReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, FAHcytosol, extracellular space

• L-glutamineReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of L-Glutamine by Atb0 Transporter

  Catalysed by CYP19A1, SLC26A4, SLC6A14cytosol, extracellular space

• dTDPReach from here →
  1. cytochrome P450 (19-oxoandrostenedione)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. pyruvate kinase (dTDP)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 4 morecytosol, extracellular space