dehydroepiandrosterone 3-sulfate

Three steps

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(out) + a dicarboxylate(in) = (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(in) + a dicarboxylate(out)

  Catalysed by STS, SLC25A35, SLC25A34, SLC22A6 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-aminobutanoateReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by STS, SLC26A6, SLC6A12cytosol, extracellular spaceOne of 4 routes

• N-benzoylglycineReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. N-benzoylglycine(out) + a dicarboxylate(in) = N-benzoylglycine(in) + a dicarboxylate(out)

  Catalysed by STS, SLC25A35, SLC25A34, SLC22A6 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. L-aspartate(in) + sulfate(out) = L-aspartate(out) + sulfate(in)
  3. transport of 3-sulfinoalanine and aspartate (cytosol to mitochondria)

  Catalysed by STS, SLC25A14, SLC25A30, SLC25A12 and 1 morecytosol, inner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 4 routes

• chenodeoxycholoyl-CoAReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + ATP + CoA = chenodeoxycholoyl-CoA + AMP + diphosphate

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

• leukotriene D4Reach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of leukotriene C4 (cytosol to extracellular)
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by SLCO1B1, GGT1, GGT5extracellular space, cytosol

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. cytochrome P450 (arachidonate)

  Catalysed by SLCO1B1, CYP4F8extracellular space, cytosol, endoplasmic reticulumOne of 2 routes

• ubiquinol-10Reach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. sulfite(in) + sulfate(out) = sulfite(out) + sulfate(in)
  3. ubiquinone-10 + hydrogen sulfide + sulfite + 2 H(+) = ubiquinol-10 + thiosulfate

  Catalysed by STS, SLC25A14, SLC25A30, SQORcytosol, inner side of the membrane, outer side of the membrane

• (R)-adrenalineReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. (R)-noradrenaline + S-adenosyl-L-methionine = (R)-adrenaline + S-adenosyl-L-homocysteine + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, PNMTextracellular space, cytosol

• CHEBI:730073Reach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. urate(in) + glutarate(out) = urate(out) + glutarate(in)
  3. Peroxidase

  Catalysed by SLC22A24, SLC22A8, MPOinner side of the membrane, outer side of the membrane, nucleusOne of 3 routes

• CHEBI:742324Reach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, COMT and 1 moreextracellular space, cytosol

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX12Bextracellular space, cytosol

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by SLCO1B1, FAAHextracellular space, cytosol

• hexanedioyl-CoAReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate + succinyl-CoA = glutaryl-CoA + succinate
  3. hexanedioate + glutaryl-CoA = hexanedioyl-CoA + glutarate

  Catalysed by SLC22A24, SLC22A8, SUGCTinner side of the membrane, outer side of the membraneOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2C9 and 2 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1B1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. dodecanoyl-CoA + (R)-carnitine = O-dodecanoyl-R-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• 7-oxolithocholateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + NAD(+) = 7-oxolithocholate + NADH + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, HSD17B10extracellular space, cytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP2C9extracellular space, cytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 24 moreextracellular space, cytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-octadecanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-eicosanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-(9Z)-octadecenoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2inner side of the membrane, outer side of the membrane

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. 4,8-dimethylnonanoyl-CoA + (R)-carnitine = O-4,8-dimethylnonanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CPT2, CRAT and 1 moreinner side of the membrane, outer side of the membrane

• O-hexanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. hexanoyl-CoA + (R)-carnitine = O-hexanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CRATinner side of the membrane, outer side of the membrane

• O-3-oxobutanoyl-(R)-carnitineReach from here →
  1. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA

  Catalysed by SLC22A24, SLC22A8, CRATinner side of the membrane, outer side of the membrane

• 11beta-prostaglandin F2Reach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1B1, AKR1C3, AKR1C2extracellular space, cytosol

• androst-5-en-3beta,7alpha,17beta-triolReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. 3beta-hydroxyandrost-5-en-17-one + NADPH + H(+) = androst-5-en-3beta,17beta-diol + NADP(+)
  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 STS, AKR1B15, HSD17B3, CYP7B1cytosol

• 6beta-hydroxyandrost-4-ene-3,17-dioneReach from here →
  1. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  2. 3beta-Hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
  3. androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxyandrost-4-ene-3,17-dione + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by STS, HSD3B1, HSD3B2, CYP3A4 and 1 morecytosol, endoplasmic reticulum

• 3-methylmalateReach from here →
  1. propanoate(out) + dehydroepiandrosterone 3-sulfate(in) = propanoate(in) + dehydroepiandrosterone 3-sulfate(out)
  2. propanoate + ATP + CoA = propanoyl-CoA + AMP + diphosphate
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by SLC22A9, ACSM3, ACSS3, ACSS2 and 2 moreinner side of the membrane, outer side of the membrane

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by SLCO1B1, TBXAS1, CYP2S1, PTGES2extracellular space, cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP4F8extracellular space, cytosol

• prostaglandin H1Reach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

  Catalysed by SLCO1B1, PTGES, PTGES3, PTGES2extracellular space, cytosolOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP4F8extracellular space, cytosol

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX15Bextracellular space, cytosol

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX15Bextracellular space, cytosol