testosterone

Three steps

• 2-oxoglutaramateReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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

• 17alpha-estradiolReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. 17alpha-estradiol + NADP(+) = estrone + NADPH + H(+)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 5 moreendoplasmic reticulum, cytosol

• 3-hydroxypyruvateReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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

• aceneuramateReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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

• CHEBI:17724Reach from here →
  1. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  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 (testosterone)
  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 moreendoplasmic reticulum, extracellular space, cytosol

• urateReach from here →
  1. cytochrome P450 (testosterone)
  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

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

  Catalysed by CYP19A1, UGT1A9, UGT2B11, UGT2B17 and 18 moreendoplasmic reticulum

• 17beta-estradiol 17-O-(3-sulfo-beta-D-glucuronate)Reach from here →
  1. cytochrome P450 (testosterone)
  2. 17beta-estradiol + UDP-alpha-D-glucuronate = 17beta-estradiol 17-O-(beta-D-glucuronate) + UDP + H(+)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate) + 3'-phosphoadenylyl sulfate = 17beta-estradiol 17-O-(3-sulfo-beta-D-glucuronate) + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by CYP19A1, UGT2B17, UGT2A1, UGT2B7 and 3 moreendoplasmic reticulum

• CHEBI:17895Reach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. retinoate reduction

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

• CHEBI:18019Reach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Peroxidase

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

• androst-4-ene-3,11,17-trioneReach from here →
  1. testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+)
  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 HSD17B6, AKR1C4, HSD17B2, AKR1C3 and 4 moreOne of 2 routes

• potassium atomReach from here →
  1. cytochrome P450 (testosterone)
  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

• 11-deoxycortisolReach from here →
  1. testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by HSD17B6, AKR1C4, HSD17B2, AKR1C3 and 4 moreendoplasmic reticulum, cytosolOne of 3 routes

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

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A1 and 1 moreendoplasmic reticulum, extracellular space, cytosol

• 2-methoxy-17beta-estradiolReach from here →
  1. cytochrome P450 (testosterone)
  2. unspecific monooxygenase (estradiol-17beta)
  3. catechol O-methyltransferase (2-hydroxyestradiol-17beta)

  Catalysed by CYP19A1, CYP1A1, CYP1A2, CYP2E1 and 23 moreendoplasmic reticulum, cytosolOne of 2 routes

• malonic acidReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  2. 17beta-estradiol + UDP-alpha-D-glucuronate = 17beta-estradiol 17-O-(beta-D-glucuronate) + UDP + H(+)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

  Catalysed by CYP19A1, UGT2B17, UGT2A1, UGT2B7 and 3 moreendoplasmic reticulum, inner side of the membrane, outer side of the membraneOne of 2 routes

• 3-oxopropanoateReach from here →
  1. cytochrome P450 (testosterone)
  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. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  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

• (R)-lactic acidReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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