testosterone

Three steps

• 2-iminopropanoateReach from here →
  1. cytochrome P450 (testosterone)
  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 (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

• 13-cis-retinalReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

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

• 3-(methylsulfanyl)propanoateReach 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. 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 (testosterone)
  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

• 3beta-hydroxy-5alpha-androstan-17-oneReach from here →
  1. dihydrotestosterone:NADP+ delta4-oxidoreductase
  2. 17beta-hydroxy-5alpha-androstan-3-one + NAD(+) = 5alpha-androstan-3,17-dione + NADH + H(+)
  3. 3beta-hydroxy-5alpha-androstan-17-one + NAD(+) = 5alpha-androstan-3,17-dione + NADH + H(+)

  Catalysed by SRD5A1, SRD5A2, SRD5A3, HSD17B2 and 4 morecytosolOne of 2 routes

• a 3-acylpyruvateReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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. 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. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by CYP19A1, ALDH9A1, PIPOX

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  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 (testosterone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate

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

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  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 (testosterone)
  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 (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, cytosolOne of 3 routes

• L-tryptophanReach from here →
  1. cytochrome P450 (testosterone)
  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. 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 + H2O = formate + glutathione + H(+)

  Catalysed by CYP19A1, ESD

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

• N-acetylputrescineReach from here →
  1. cytochrome P450 (testosterone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N-acetylputrescine + H2O = putrescine + acetate

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

• 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. testosterone + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 17beta-estradiol + 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 (testosterone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

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

• (3S)-citramalyl-CoAReach from here →
  1. cytochrome P450 (testosterone)
  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 (testosterone)
  2. transport of acetate and formate (cytosol to extracellular)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

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

• 5-amino-2-oxopentanoateReach from here →
  1. cytochrome P450 (testosterone)
  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. 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. 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 (testosterone)
  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

• estrone 3-sulfateReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. 3'-Phosphoadenylylsulfate:estrone 3-sulfotransferase

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 7 moreendoplasmic reticulum, cytosolOne of 3 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (testosterone)
  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

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. cytochrome P450 (testosterone)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

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

• 16alpha,17alpha-dihydroxyprogesteroneReach from here →
  1. testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. 17alpha-hydroxyprogesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17alpha-dihydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by HSD17B6, AKR1C4, HSD17B2, AKR1C3 and 3 moreendoplasmic reticulum

• 16alpha-hydroxyestroneReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. unspecific monooxygenase (estrone)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 27 moreendoplasmic reticulum, cytosolOne of 3 routes

• 19-oxo-androst-4-ene-3,17-dioneReach from here →
  1. testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+)
  2. 19-hydroxyandrostenedione,NADPH-hemoprotein reductase:oxygen 19-oxidoreductase
  3. cytochrome P450 (19-hydroxyandrostenedione)

  Catalysed by HSD17B6, AKR1C4, HSD17B2, AKR1C3 and 3 morecytosolOne of 2 routes

• androst-5-en-3beta,7alpha,17beta-triolReach from here →
  1. dihydrotestosterone:NADP+ delta4-oxidoreductase
  2. 3beta-hydroxy-Delta(5)-steroid dehydrogenase (5-alpha-dihydrotestosterone)
  3. androst-5-en-3beta,17beta-diol + reduced [NADPH--hemoprotein reductase] + O2 = androst-5-en-3beta,7alpha,17beta-triol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SRD5A1, SRD5A2, SRD5A3, HSD3B1 and 2 morecytosol

• 4-hydroxyestroneReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP19A1, HSD17B6, HSD17B1, HSD17B2 and 10 moreendoplasmic reticulum, cytosol

• 6alpha-hydroxyestroneReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 6alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 15alpha-hydroxyestroneReach from here →
  1. cytochrome P450 (testosterone)
  2. Estradiol-17beta:NADP+ 17-oxidoreductase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 15alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 2-hydroxy-3-methoxy-17beta-estradiolReach from here →
  1. cytochrome P450 (testosterone)
  2. unspecific monooxygenase (estradiol-17beta)
  3. 2-hydroxy-17beta-estradiol + S-adenosyl-L-methionine = 2-hydroxy-3-methoxy-17beta-estradiol + S-adenosyl-L-homocysteine + H(+)

  Catalysed by CYP19A1, CYP1A1, CYP1A2, CYP2E1 and 22 moreendoplasmic reticulum, cytosol

• 3beta-hydroxy-5beta-androstane-17-oneReach from here →
  1. testosterone + NAD(+) = androst-4-ene-3,17-dione + NADH + H(+)
  2. androst-4-ene-3,17-dione + NADPH + H(+) = 5beta-androstane-3,17-dione + NADP(+)
  3. 5beta-androstane-3,17-dione + NADPH + H(+) = 3beta-hydroxy-5beta-androstane-17-one + NADP(+)

  Catalysed by HSD17B6, AKR1C4, HSD17B2, AKR1C3 and 4 more

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. cytochrome P450 (testosterone)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by CYP19A1, SLC16A4, SLC16A5, SLC16A7 and 5 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrix