3,3',5-triiodo-L-thyronine

Three steps

• dopamine 3-O-sulfateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. dopamine + 3'-phosphoadenylyl sulfate = dopamine 3-O-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT1B1, SULT1A3 and 2 moreextracellular space, cytosol

• dopamine 4-O-sulfateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of dopamine and GSH (cytosol to extracellular)
  3. Dopamine 4-O-Sulfotransferase

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A1extracellular space, cytosolOne of 2 routes

• hyocholateReach from here →
  1. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. Chenodeoxycholic acid 6alpha-hydroxylase

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• prostaglandin A2-S-(R)-glutathioneReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of GSH and prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, GSTA1 and 1 moreextracellular space, cytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of GSH and prostaglandin A2 (cytosol to extracellular)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, GSTP1 and 1 moreextracellular space, cytosol

• 13-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = 9-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15extracellular space, cytosol

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by SLCO1A2, SLCO1B3, ALOX15extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLCO1A2, SLCO1B3, PM20D1extracellular space, cytosol

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosolOne of 2 routes

• cholesterol sulfateReach from here →
  1. aryl sulfotransferase (PAPS)
  2. steroid sulfatase (3,5,3-triiodothyronine-4-sulfate)
  3. Steryl-Sulfatase

  Catalysed by SULT1A3, SULT1A4, SULT1A1, SULT1A2 and 1 morecytosol, Golgi apparatusOne of 2 routes

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, CYP2C9extracellular space, cytosol

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13R)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 2 more

• chenodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + UDP-alpha-D-glucuronate = chenodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by SLCO1A2, SLCO1B3, UGT2A2, UGT1A3extracellular space, cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. aryl sulfotransferase (PAPS)
  2. steroid sulfatase (3,5,3-triiodothyronine-4-sulfate)
  3. steroid sulfatase (5-alpha-dihydrotestosterone)

  Catalysed by SULT1A3, SULT1A4, SULT1A1, SULT1A2 and 1 morecytosolOne of 3 routes

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1A2, SLCO1B3, CYP1A1, CYP1A2 and 24 moreextracellular space, cytosol

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by DIO1, DIO3, AIFM1, PYROXD1 and 1 more

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 5 moreextracellular space, cytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

  Catalysed by DIO1, DIO3, RETSAT, AWAT2

• an aryl sulfateReach from here →
  1. aryl sulfotransferase (PAPS)
  2. steroid sulfatase (3,5,3-triiodothyronine-4-sulfate)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SULT1A3, SULT1A4, SULT1A1, SULT1A2 and 7 morecytosol

• beta-D-glucosyl-(1->3)-O-chenodeoxycholateReach from here →
  1. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, GBA2extracellular space, cytosolOne of 2 routes

• L-cystine-bis-glycineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. 2 L-cysteinylglycine + [protein]-disulfide = L-cystine-bis-glycine + [protein]-dithiol

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 5 moreextracellular space, cytosol

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by SLCO1A2, SLCO1B3extracellular space, cytosolOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by SLCO1A2, SLCO1B3, FAAH, PM20D1extracellular space, cytosol

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of GSH and prostaglandin G2 (cytosol to extracellular)
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1, PTGESextracellular space, cytosol

• cholineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of acetylcholine and GSH (cytosol to extracellular)
  3. Acetylcholine aectylhydrolase

  Catalysed by SLCO1A2, SLCO1B3, BCHE, ACHEextracellular space, cytosolOne of 6 routes

• pyruvateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by SLCO1A2, SLCO1B3, CTHextracellular space, cytosolOne of 6 routes

• arachidonoyl-CoAReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, SLC27A2, ACSL4 and 6 moreextracellular space, cytosolOne of 3 routes

• CHEBI:15519Reach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. Cholate:CoA ligase (AMP-forming)

  Catalysed by SLCO1A2, SLCO1B3, SLC27A2, SLC27A5extracellular space, cytosol, endoplasmic reticulum

• (S)-malateReach from here →
  1. aryl sulfotransferase (PAPS)
  2. steroid sulfatase (3,5,3-triiodothyronine-4-sulfate)
  3. transport of malate and sulfate (cytosol to mitochondria)

  Catalysed by SULT1A3, SULT1A4, SULT1A1, SULT1A2 and 2 morecytosol, mitochondrial matrixOne of 9 routes

• L-leucineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and leucine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A9, SLC3A1extracellular space, cytosolOne of 5 routes

• 12(S)-HPETEReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX12extracellular space, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. Glutathione: 5-HPETE oxidoreductase
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 7 moreextracellular space, cytosolOne of 6 routes

• 5(S)-HPETEReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, ALOX5extracellular space, cytosol

• all-trans-3-hydroxyretinolReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by DIO1, DIO3, RETSAT, CYP27C1

• CHEBI:15699Reach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and homoserine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 3 routes

• formateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ADH1C, ADH1A and 5 moreextracellular space, cytosolOne of 2 routes

• malonateReach from here →
  1. aryl sulfotransferase (PAPS)
  2. steroid sulfatase (3,5,3-triiodothyronine-4-sulfate)
  3. malonate(in) + sulfate(out) = malonate(out) + sulfate(in)

  Catalysed by SULT1A3, SULT1A4, SULT1A1, SULT1A2 and 4 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:15971Reach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and histidine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A6extracellular space, cytosolOne of 3 routes

• (R)-lactateReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-lactoylglutathione + H2O = (R)-lactate + glutathione + H(+)

  Catalysed by SLCO1A2, SLCO1B3, GLO1, GLOD4 and 1 moreextracellular space, cytosol

• methanethiolReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by DIO1, DIO3, KDM1A, KDM1B and 1 more

• octan-1-olReach from here →
  1. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. octyl beta-D-glucose + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + octan-1-ol

  Catalysed by SLCO1A2, SLCO1B3, GBA2extracellular space, cytosol

• L-cystineReach from here →
  1. transport of GSH and triiodothyronine (cytosol to extracellular)
  2. Glutathione: 5-HPETE oxidoreductase
  3. cystine to cysteine conversion

  Catalysed by SLCO1A2, SLCO1B3, GPX5, GPX1 and 7 moreextracellular space, cytosolOne of 5 routes

• 11-cis-retinolReach from here →
  1. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-Retinol 11-cis-trans-isomerase

  Catalysed by DIO1, DIO3, RETSATcytosolOne of 2 routes