N-decanoylglycine

Three steps

• octanoateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. Fatty Acid Beta Oxidation (C10->C8), Peroxisomal
  3. Octanoyl-CoA hydrolase

  Catalysed by GLYATL2, ACAA1, HSD17B4, EHHADH and 2 moreperoxisome, cytosolOne of 2 routes

• potassium atomReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of chloride and glycine (cytosol to extracellular)
  3. transport of chloride (cytosol to extracellular)

  Catalysed by GLYATL2, SLC6A9, SLC6A14, SLC12A2 and 1 moreextracellular space, cytosolOne of 2 routes

• CHEBI:27540Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by GLYATL2, BAAT, ACSM4, ACSM1 and 4 moreperoxisome, cytosolOne of 7 routes

• elaidic acidReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (elaidate)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 5 routes

• 5-hydroxytryptophanReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)

  Catalysed by GLYATL2, SLC7A5, TPH1, TPH2extracellular space, cytosolOne of 2 routes

• 5(S)-HETEReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Glutathione: 5-HPETE oxidoreductase

  Catalysed by GLYATL2, GSS, GPX5, GPX1 and 7 morecytosolOne of 2 routes

• CHEBI:28701Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by GLYATL2, BAAT, ACAA1, SCP2 and 1 moreperoxisomeOne of 7 routes

• pyridoxine 5'-phosphateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of alanine and glycine (cytosol to extracellular)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A10 and 1 moreextracellular space, cytosol

• N-acetyl-L-cysteineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. Hippurate (Benzoylglycinate) Formation
  3. N-benzoylglycine(out) + a dicarboxylate(in) = N-benzoylglycine(in) + a dicarboxylate(out)

  Catalysed by GLYATL2, SLC22A6, SLC22A8mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• iron(2+)Reach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. Fe(3+)(out) + L-ascorbate(in) = monodehydro-L-ascorbate radical(in) + Fe(2+)(out) + H(+)

  Catalysed by PAM, CYB561D2, CYB561, CYBRD1 and 2 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• K(+)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• Cys-tRNA(Cys)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosol

• Phe-tRNA(Phe)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by GLYATL2, SLC7A5, FARSB, FARSAextracellular space, cytosol

• Trp-tRNA(Trp)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. L-Tryptophan -tRNA(Trp) ligase (AMP-forming)

  Catalysed by GLYATL2, SLC7A5, WARS1extracellular space, cytosol

• Ile-tRNA(Ile)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-Isoleucine:tRNA(Ile) ligase (AMP-forming)

  Catalysed by GLYATL2, SLC7A5, IARS1extracellular space, cytosol

• Gln-tRNA(Gln)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. L-Glutamine:tRNA(Gln) ligase (AMP-forming)

  Catalysed by GLYATL2, SLC7A5, QARS1extracellular space, cytosol

• isocyanateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. L-citrulline + H(+) = isocyanate + L-ornithine

  Catalysed by GLYATL2, SLC7A9, SLC3A1, SLC7A6 and 1 moreextracellular space, cytosol

• Asn-tRNA(Asn)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of asparagine and glycine (cytosol to extracellular)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

  Catalysed by GLYATL2, NARS1extracellular space, cytosol

• cholateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (cholate)

  Catalysed by GLYATL2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 3 routes

• glycolateReach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate
  3. glycolate + NADP(+) = glyoxylate + NADPH + H(+)

  Catalysed by PAM, GRHPROne of 3 routes

• hydrogen sulfideReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosolOne of 3 routes

• L-aspartateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of alanine and glycine (cytosol to extracellular)
  3. oxaloacetate + L-alanine = L-aspartate + pyruvate

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A10 and 1 moreextracellular space, cytosolOne of 21 routes

• CHEBI:30249Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)

  Catalysed by GLYATL2, SLC7A5, IDO1, TDO2 and 1 moreextracellular space, cytosol

• oxalateReach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate
  3. glyoxylate + O2 + H2O = oxalate + H2O2 + H(+)

  Catalysed by PAM, HAO1

• formic acidReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of chloride and glycine (cytosol to extracellular)
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by GLYATL2, SLC6A9, SLC6A14, SLC26A4extracellular space, cytosolOne of 2 routes

• malonic acidReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of chloride and glycine (cytosol to extracellular)
  3. Malonate Transport, Antiport with Chloride

  Catalysed by GLYATL2, SLC6A9, SLC6A14extracellular space, cytosolOne of 2 routes

• (9Z)-octadecenoateReach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O

  Catalysed by PAM, FAAH, PM20D1

• an alcoholReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O

  Catalysed by GLYATL2, GSS, CP, PRDX6

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

  Catalysed by GLYATL2, BAAT, SLC22A24peroxisome, inner side of the membrane, outer side of the membraneOne of 2 routes

• decanalReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. Decanoyl-CoA hydrolase
  3. decanal + NAD(+) + H2O = decanoate + NADH + 2 H(+)

  Catalysed by GLYATL2, ACOT7, ALDH3A2cytosol

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by GLYATL2, GSScytosol, extracellular spaceOne of 3 routes

• L-lysineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine(out) + L-lysine(in) = L-ornithine(in) + L-lysine(out)

  Catalysed by GLYATL2, GATM, SLC25A2, SLC25A15cytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• D-lysineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. L-Arginine:glycine amidinotransferase
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by GLYATL2, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• putrescineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine carboxy-lyase (putrescine-forming)

  Catalysed by GLYATL2, GATM, ODC1cytosolOne of 4 routes

• D-arginineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. L-Arginine:glycine amidinotransferase
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by GLYATL2, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and methionine (cytosol to extracellular)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by GLYATL2, SLC7A5, IL4I1extracellular space, cytosol

• di-mu-sulfido-diiron(2+)Reach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. De novo synthesis of 2Fe2S

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 7 moreextracellular space, cytosol, mitochondrial matrix

• serotoninReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and serotonin (cytosol to extracellular)

  Catalysed by GLYATL2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

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

  Catalysed by GLYATL2, SLC7A5, BCAT2, BCAT1extracellular space, cytosol

• D-cysteineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of alanine and glycine (cytosol to extracellular)
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A10extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-serineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of alanine and glycine (cytosol to extracellular)
  3. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A10extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 10 routes

• 3-methyl-2-oxovaleric acidReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by GLYATL2, SLC7A5, BCAT1extracellular space, cytosolOne of 2 routes

• 3-(4-hydroxyphenyl)pyruvateReach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by PAM, AADATOne of 7 routes

• taurocholateReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (GSH)

  Catalysed by GLYATL2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 3 routes

• tert-butanolReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. tert-butyl hydroperoxide + 2 glutathione = tert-butanol + glutathione disulfide + H2O

  Catalysed by GLYATL2, GSS, CLIC2, GPX1 and 3 more

• Cu(+)Reach from here →
  1. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. Cu(2+)(out) + L-ascorbate(in) = Cu(+)(out) + monodehydro-L-ascorbate radical(in) + H(+)

  Catalysed by PAM, CYBRD1inner side of the membrane, outer side of the membraneOne of 3 routes

• gamma-Glu-AlaReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by GLYATL2, GSS, GGT1, GGT5 and 4 morecytosol, extracellular spaceOne of 2 routes

• taurineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by GLYATL2, BAATperoxisome, cytosolOne of 4 routes

• 3,3',5-triiodo-L-thyronineReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and triiodothyronine (cytosol to extracellular)

  Catalysed by GLYATL2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes