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Pathways

androgen and estrogen metabolism (BRENDA)

:= BRENDA,

:= KEGG,

:= MetaCyc,

:= SABIO-RK

:= amino acid sequences

:= show the reaction diagram

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EC Number

Reaction

Pathways

Reaction IDs

Stoichiometry Check

Missing Substrate

Missing Product

Commentary

Remark

1.13.11.25

3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione 4,5-dioxygenase

3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O2 = 3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic)

: BR40480

: R04597

: 1.13.11.25-RXN

: 4266

natural substrates

1.14.14.12

3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione monooxygenase

3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH2 + O2 = 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H2O

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androstenedione degradation I (aerobic)

: BR49866

: R09819

: RXN-12717

: FMN is re-reduced by NADH (see R05705)

natural substrates

SPONTANEOUS

9alpha-hydroxyandrosta-1,4-diene-3,17-dione = 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androstenedione degradation I (aerobic)

: BR52868

: R09885

: RXN-12715

: spontaneous following after R09860

natural substrates

0.0.0.0

spontaneous reaction

9alpha-hydroxyandrosta-1,4-diene-3,17-dione = 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androstenedione degradation I (aerobic)

: BR52868

: R09885

: RXN-12715

: spontaneous following after R09860

natural substrates

1.14.15.30

3-ketosteroid 9alpha-monooxygenase

androsta-1,4-diene-3,17-dione + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 9alpha-hydroxyandrosta-1,4-diene-3,17-dione + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androstenedione degradation I (aerobic)

: BR49974

: R09860

: RXN-12691

generic compounds

: subsequently R09885

natural substrates, generic, protein

1.3.99.4

3-oxosteroid 1-dehydrogenase

4-androstene-3,17-dione + acceptor = 1,4-androstene-3,17-dione + reduced acceptor

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androsrtendione degradation II (anaerobic),
androstenedione degradation I (aerobic)

: BS258852

: R09884

: RXN-12714

natural substrates, generic

1.1.1.112

indanol dehydrogenase

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.210

3beta(or 20alpha)-hydroxysteroid dehydrogenase

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.239

3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.357

3alpha-hydroxysteroid 3-dehydrogenase

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.51

3(or 17)beta-hydroxysteroid dehydrogenase

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.62

17beta-estradiol 17-dehydrogenase

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.1.1.64

testosterone 17beta-dehydrogenase (NADP+)

testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic)

: BR29275

: R01836

: 1.1.1.51-RXN_WOP

, TESTOSTERONE-17-BETA-DEHYDROGENASE-RXN

: 1915

: NADP+ (see R01838)

natural substrates

1.14.15.6

cholesterol monooxygenase (side-chain-cleaving)

cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin

: androgen and estrogen metabolism

: BR29153

, BS386399

: R02724

: 1.14.15.6-RXN

: 2614

: three-step reaction (R01454+R04854+R03933 or R02723+R04855+R03933)

natural substrates

1.14.14.32

17alpha-hydroxyprogesterone deacetylase

17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O

: androgen and estrogen metabolism

: Steroid hormone biosynthesis

: BR362

: R08518

: 17alpha-hydroxylase/17,20-lyase

natural substrates, generic, protein

1.1.1.146

11beta-hydroxysteroid dehydrogenase

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.148

estradiol 17alpha-dehydrogenase

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.184

carbonyl reductase (NADPH)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.2

alcohol dehydrogenase (NADP+)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.209

3(or 17)alpha-hydroxysteroid dehydrogenase

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.213

3alpha-hydroxysteroid 3-dehydrogenase (Re-specific)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.239

3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.50

3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.51

3(or 17)beta-hydroxysteroid dehydrogenase

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.62

17beta-estradiol 17-dehydrogenase

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

1.1.1.64

testosterone 17beta-dehydrogenase (NADP+)

testosterone + NADP+ = androstenedione + NADPH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: testosterone and androsterone degradation to androstendione (aerobic),
androgen biosynthesis

: BR29315

, BS438469

: R01838

: 1.1.1.51-RXN

, 1.1.1.64-RXN

: 1917

: NAD+ (see R01836)

natural substrates

5.3.3.1

steroid DELTA-isomerase

pregnenolone + NAD+ = progesterone + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Metabolic pathways

: BS383305

: R02216

: RXN-9722

: 2188

: 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase two-step reaction

natural substrates

pregnenolone + NAD+ = progesterone + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Metabolic pathways

: BS383305

: R02216

: RXN-9722

: 2188

: 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase two-step reaction

natural substrates

1.1.1.145

3beta-hydroxy-DELTA5-steroid dehydrogenase

pregnenolone + NAD+ = progesterone + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Metabolic pathways

: BS383305

: R02216

: RXN-9722

: 2188

: 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase two-step reaction

natural substrates

1.1.1.51

3(or 17)beta-hydroxysteroid dehydrogenase

pregnenolone + NAD+ = progesterone + NADH + H+

: androgen and estrogen metabolism

: Steroid hormone biosynthesis,
Metabolic pathways

: BS383305

: R02216

: RXN-9722

: 2188

: 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase two-step reaction

natural substrates

3.7.1.17

4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase

(1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate + H2O = 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + (2Z,4Z)-2-hydroxyhexa-2,4-dienoate

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic)

: BR49990

: R09883

: RXN-12718

natural substrates

4.1.3.43

4-hydroxy-2-oxohexanoate aldolase

(S)-4-hydroxy-2-oxohexanoate = propanal + pyruvate

: androgen and estrogen metabolism

: toluene degradation to 2-hydroxypentadienoate (via 4-methylcatechol),
androstenedione degradation I (aerobic),
4-nitrotoluene degradation II

: BR50714

: RXN-12735

natural substrates

1.2.1.10

acetaldehyde dehydrogenase (acetylating)

propanal + CoA + NAD+ = propanoyl-CoA + NADH + H+

: propanol degradation,
androgen and estrogen metabolism

: Xylene degradation,
Propanoate metabolism,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic),
(S)-propane-1,2-diol degradation

: BR50602

: R09097

: RXN-12736

: 10853

natural substrates

1.2.1.27

methylmalonate-semialdehyde dehydrogenase (CoA-acylating)

propanal + CoA + NAD+ = propanoyl-CoA + NADH + H+

: propanol degradation,
androgen and estrogen metabolism

: Xylene degradation,
Propanoate metabolism,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic),
(S)-propane-1,2-diol degradation

: BR50602

: R09097

: RXN-12736

: 10853

natural substrates

1.2.1.57

butanal dehydrogenase

propanal + CoA + NAD+ = propanoyl-CoA + NADH + H+

: propanol degradation,
androgen and estrogen metabolism

: Xylene degradation,
Propanoate metabolism,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic),
(S)-propane-1,2-diol degradation

: BR50602

: R09097

: RXN-12736

: 10853

natural substrates

1.2.1.87

propanal dehydrogenase (CoA-propanoylating)

propanal + CoA + NAD+ = propanoyl-CoA + NADH + H+

: propanol degradation,
androgen and estrogen metabolism

: Xylene degradation,
Propanoate metabolism,
Metabolic pathways,
Microbial metabolism in diverse environments,
Degradation of aromatic compounds

: androstenedione degradation I (aerobic),
(S)-propane-1,2-diol degradation

: BR50602

: R09097

: RXN-12736

: 10853

natural substrates

6.2.1.41

3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate-CoA ligase

ATP + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + CoA = AMP + diphosphate + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA

: androgen and estrogen metabolism

: Steroid degradation,
Metabolic pathways,
Microbial metabolism in diverse environments

: androsrtendione degradation II (anaerobic),
androstenedione degradation I (aerobic)

: BR51067

: R10769

: RXN-12746

natural substrates