glycodeoxycholate

Three steps

• (9Z)-octadecenoateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)
  3. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O

  Catalysed by GLYATL3, GLYATL2, FAAH, PM20D1cytosol

• (S)-dihydroorotateReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. (S)-dihydroorotate + a quinone = orotate + a quinol

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

• glutarateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)

  Catalysed by BAAT, SLC22A24cytosol, peroxisome, inner side of the membrane, outer side of the membraneOne of 6 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by GSScytosol, extracellular spaceOne of 5 routes

• nicotinateReach 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. nicotinate(in) + urate(out) = nicotinate(out) + urate(in)

  Catalysed by ABCC4, SLC22A13, SLC22A12inner side of the membrane, outer side of the membrane

• L-lysineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine(out) + L-lysine(in) = L-ornithine(in) + L-lysine(out)

  Catalysed by GATM, SLC25A2, SLC25A15cytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• D-lysineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-Arginine:glycine amidinotransferase
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• putrescineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine carboxy-lyase (putrescine-forming)

  Catalysed by GATM, ODC1cytosolOne of 4 routes

• D-arginineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. L-Arginine:glycine amidinotransferase
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• a carboxylic esterReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O
  3. a carboxylic ester + H2O = an alcohol + a carboxylate + H(+)

  Catalysed by ABCC4, CP, PRDX6, CES2 and 4 moreinner side of the membrane, outer side of the membrane

• methylarsonateReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by ABCC4, GSR, GSTO1, GSTO2inner side of the membrane, outer side of the membraneOne of 2 routes

• thiosulfateReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by ABCC4, GSR, TSTD1inner side of the membrane, outer side of the membraneOne of 11 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and methionine (cytosol to extracellular)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by SLC7A5, IL4I1cytosol, extracellular space

• di-mu-sulfido-diiron(2+)Reach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. De novo synthesis of 2Fe2S

  Catalysed by SLC3A2, SLC7A5, SLC7A8, NDUFAB1 and 6 morecytosol, extracellular space, mitochondrial matrix

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

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

• (S)-3-methyl-2-oxopentanoateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate

  Catalysed by SLC7A5, BCAT2, BCAT1cytosol, extracellular space

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

  Catalysed by SLC3A2, SLC7A5, SLC7A10cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by SLC3A2, SLC7A5, SLC7A10cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 10 routes

• a hydroperoxideReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O
  3. a hydroperoxide + [thioredoxin]-dithiol = an alcohol + [thioredoxin]-disulfide + H2O

  Catalysed by ABCC4, CP, PRDX6, PRDX5 and 4 moreinner side of the membrane, outer side of the membrane

• 3-methyl-2-oxovaleric acidReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by SLC7A5, BCAT1cytosol, extracellular spaceOne of 2 routes

• chenodeoxycholateReach 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. solute carrier organic anion transporter (chenodiol)

  Catalysed by ABCC4, PTGES, LANCL1, GSTM4 and 3 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 3-(4-hydroxyphenyl)pyruvateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. transport of glycine and tyrosine (cytosol to extracellular)
  3. L-tyrosine:2-oxoglutarate aminotransferase

  Catalysed by SLC7A5, GOT2, GOT1, TATcytosol, extracellular spaceOne of 7 routes

• taurodeoxycholateReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, SLC27A5, BAATcytosolOne of 2 routes

• (R)-lactic acidReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. (R)-S-lactoylglutathione = methylglyoxal + glutathione
  3. (R)-S-Lactoylglutathione hydrolase

  Catalysed by ABCC4, GLO1, HAGH, HAGHLinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• (S)-lactic acidReach 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. transport of L-lactate and urate (cytosol to extracellular)

  Catalysed by ABCC4, SLC22A13, SLC22A12inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• Cu(+)Reach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. L-dehydroascorbate + 2 glutathione = glutathione disulfide + L-ascorbate
  3. Cu(2+)(out) + L-ascorbate(in) = Cu(+)(out) + monodehydro-L-ascorbate radical(in) + H(+)

  Catalysed by ABCC4, CLIC1, GSTO1, GSTO2 and 1 moreinner side of the membrane, outer side of the membrane

• gamma-Glu-AlaReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by GSS, GGT1, GGT5, GGTLC2 and 3 morecytosol, extracellular spaceOne of 2 routes

• taurineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by BAATcytosol, peroxisomeOne of 4 routes

• 3,3',5-triiodo-L-thyronineReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and triiodothyronine (cytosol to extracellular)

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

• 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamideReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. a quinone + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + a quinol
  3. 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H(+) = beta-nicotinamide D-riboside + a quinol

  Catalysed by ABCC4, SQOR, NQO2inner side of the membrane, outer side of the membrane

• (R)-methylmalonyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by BAAT, ALDH6A1cytosol, peroxisome, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by BAATcytosol, peroxisome, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by BAAT, ACP2cytosol, peroxisome, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by BAATcytosol, peroxisome, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by BAAT, ACAA1, MYO5Bcytosol, peroxisomeOne of 2 routes

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

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

• benzoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. Hippurate (Benzoylglycinate) Formation
  3. benzoyl-CoA + glycine = N-benzoylglycine + CoA + H(+)

  Catalysed by GLYATcytosol, mitochondrial matrix

• butanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by BAAT, ACSM4, ACSM1, ACSM2A and 3 morecytosol, peroxisomeOne of 9 routes

• choloyl-CoAReach from here →
  1. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. cholate + ATP + CoA = choloyl-CoA + AMP + diphosphate

  Catalysed by ABCC4, SLC27A5inner side of the membrane, outer side of the membrane

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

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

• glutaryl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Glutaryl Carnitine

  Catalysed by BAAT, CPT1A, CPT1C, CPT1Bcytosol, peroxisomeOne of 2 routes

• hexadecanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by GLYATL3cytosol

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

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 12 routes

• itaconyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by BAAT, SUCLG1, SUCLG2, SUCLA2cytosol, peroxisome, mitochondrial matrixOne of 2 routes

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

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 14 routes

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

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, peroxisomeOne of 12 routes

• octanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by BAAT, CROTcytosol, peroxisome, mitochondrial matrixOne of 21 routes

• phytanoyl-CoAReach from here →
  1. Glycodeoxycholate amidohydrolase
  2. bile acid-CoA: amino acid N-acyltransferase
  3. phytanate-CoA ligase

  Catalysed by BAATcytosol, peroxisomeOne of 5 routes

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

  Catalysed by BAAT, SLC27A2, ACSL4, ACSL3 and 4 morecytosol, peroxisomeOne of 15 routes

• prostaglandin E1Reach from here →
  1. Glycodeoxycholate amidohydrolase
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin E1 (cytosol to extracellular)

  Catalysed by GSS, SLCO2A1cytosol, extracellular spaceOne of 4 routes