(R)-noradrenaline

Three steps

• L-methionineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and methionine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 8 routes

• L-tryptophanReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and tryptophan (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 4 routes

• glutathioneReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, ABCC4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 16 routes

• L-alanineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. glutathione gamma-glutamylaminopeptidase
  3. gamma-glutamyltransferase (alanine)

  Catalysed by SLCO1A2, SLCO1B3, GGTLC3, GGT1 and 4 moreextracellular space, cytosolOne of 16 routes

• L-asparagineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of asparagine and cysteine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 4 routes

• L-phenylalanineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and phenylalanine (cytosol to extracellular)

  Catalysed by SLCO1A2, SLCO1B3, SLC7A5extracellular space, cytosolOne of 6 routes

• L,L-cystathionineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. Formation of Homocystine
  3. L-serine hydro-lyase (adding homocysteine

  Catalysed by SLCO1A2, SLCO1B3, CBSextracellular space, cytosol

• gamma-L-glutamyl-L-cysteineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by SLCO1A2, SLCO1B3, GCLC, GCLMextracellular space, cytosolOne of 2 routes

• S-sulfanyl-L-cysteineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by SLCO1A2, SLCO1B3, CARS2extracellular space, cytosol

• N(tau)-methylhistamineReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:histamine N-tele-methyltransferase

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

• hyodeoxycholateReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. transport of lithocholate (cytosol to extracellular)
  3. cytochrome P450 (lithocholate)

  Catalysed by SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

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

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

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

• monodehydro-L-ascorbate radicalReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. dopamine + 2 L-ascorbate + O2 = (R)-noradrenaline + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosolOne of 9 routes

• 3-sulfino-L-alanineReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, CDO1extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, GGT1 and 1 moreextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol, endoplasmic reticulumOne of 2 routes

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

  Catalysed by SLCO1A2, SLCO1B3, COMT, LRTOMTextracellular space, cytosol

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ALOX12Bextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

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

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

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 4 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

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

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

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, PTGS2extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. transport of GSH and noradrenaline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by SLCO1A2, SLCO1B3, MOCOSextracellular space, cytosol

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, CYP2C9extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 26 moreextracellular space, cytosolOne of 4 routes

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP1A1 and 25 moreextracellular space, cytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ABHD16Aextracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, AKR1C3 and 1 moreextracellular space, cytosol

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. transport of noradrenaline (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, CYP3A7extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, TBXAS1 and 2 moreextracellular space, cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol

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

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, PTGES and 2 moreextracellular space, cytosolOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, CYP4F8extracellular space, cytosol

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ALOX15Bextracellular space, cytosol

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of noradrenaline (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 SLCO1A2, SLCO1B3, SLCO1B1, ALOX15Bextracellular space, cytosol