glycodeoxycholate

Three steps

• N-formyl-L-kynurenineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 = N-formyl-L-kynurenine

  Catalysed by SLC7A5, IDO1, TDO2, IDO2cytosol, extracellular space

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by BAAT, SLC27A2, SLC27A5cytosol, peroxisome, endoplasmic reticulumOne of 3 routes

• 5-phospho-beta-D-ribosylamineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by SLC7A5, PPATcytosol, extracellular spaceOne of 2 routes

• D-glucosamine 6-phosphateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by SLC7A5, GFPT2, GFPT1cytosol, extracellular space

• L-methionine (S)-S-oxideReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by SLC7A5, MSRAcytosol, extracellular space

• L-methionine (R)-S-oxideReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by SLC7A5, MSRB3, MSRB1, MSRB2cytosol, extracellular space

• 5-amino-2-oxopentanoateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by GATM, AGXT2cytosolOne of 3 routes

• methylamineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine

  Catalysed by AGXT2, DDAH1cytosol

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

  Catalysed by SLC3A2, SLC7A5, SLC7A8, PPCScytosol, extracellular spaceOne of 4 routes

• monodehydro-L-ascorbate radicalReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)
  3. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by GLYATL3, GLYATL2, PAMcytosolOne of 16 routes

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine

  Catalysed by AADAT, PAHcytosol

• 4-aminobutanoateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of chloride and glycine (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by SLC6A9, SLC6A14, SLC6A12cytosol, extracellular spaceOne of 4 routes

• 3-iodo-L-tyrosineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by SLC7A5, TPOcytosol, extracellular spaceOne of 2 routes

• dopamineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of dopamine and GSH (cytosol to extracellular)

  Catalysed by GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• glycolithocholate 3-sulfateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA:amino acid N-acyltransferase (glycine)
  3. sulfotransferase (glycolithocholate)

  Catalysed by BAAT, SULT2A1cytosolOne of 5 routes

• L-prolineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of alanine and glycine (cytosol to extracellular)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by SLC3A2, SLC7A5, SLC7A10, SLC1A4cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 3 routes

• estrone 3-sulfateReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. 1-chloro-2,4-dinitrobenzene + glutathione = 2,4-dinitrophenyl-S-glutathione + chloride + H(+)
  3. transport of estrone 3-sulfate (cytosol to extracellular)

  Catalysed by ABCC4, PTGES, LANCL1, GSTM4 and 2 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• prostaglandin E2Reach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin E2 (cytosol to extracellular)

  Catalysed by GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• 3-sulfino-L-alanineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by SLC3A2, SLC7A5, SLC7A8, CDO1cytosol, extracellular spaceOne of 2 routes

• decanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by BAAT, ACSM4, ACSM1, ACSM2A and 3 morecytosol, peroxisomeOne of 8 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by BAAT, CPT1A, CPT1C, CPT1Bcytosol, peroxisomeOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 11 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by AADAT, HOGA1cytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by BAAT, CPT1A, CPT1Bcytosol, peroxisome

• leukotriene D4Reach from here →
  1. Glycodeoxycholate amidohydrolase
  2. leukotriene C4 hydrolysis
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by GGT1, GGT5cytosol

• CHEBI:63544Reach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 7 routes

• 3-demethylubiquinol-10Reach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10
  3. 3-demethylubiquinol-10 + S-adenosyl-L-methionine = ubiquinol-10 + S-adenosyl-L-homocysteine + H(+)

  Catalysed by ABCC4, SQOR, COQ3inner side of the membrane, outer side of the membrane

• hexacosanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 5 routes

• tetracosanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 10 routes

• docosanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 9 routes

• N(5)-[(Z)-amino(hydroxyimino)methyl]ornithineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of arginine and glycine (cytosol to extracellular)
  3. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)

  Catalysed by SLC7A6, NOS3, NOS1, NOS2cytosol, extracellular space

• xanthurenateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O

  Catalysed by AADAT, KYAT3cytosol

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

  Catalysed by SLC3A2, SLC7A5, SLC7A10, MOCOScytosol, extracellular space

• (2E)-octadecenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by BAAT, CPT1A, CPT1C, CPT1Bcytosol, peroxisomeOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 8 routes

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by AADAT, HOGA1cytosol

• (R)-noradrenalineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and noradrenaline (cytosol to extracellular)

  Catalysed by GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 5 routes

• CHEBI:730073Reach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. urate(out) + glutathione(in) = urate(in) + glutathione(out)
  3. Peroxidase

  Catalysed by ABCC4, SLC22A13, MPOinner side of the membrane, outer side of the membrane, nucleusOne of 3 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 6 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 7 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 6 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 7 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 5 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 4 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 6 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 4 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 5 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 5 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 7 routes