N-dodecanoylglycine

Three steps

• L-2-aminopentanoateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  3. 2-oxopentanoate + N(omega),N(omega)-dimethyl-L-arginine = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-2-aminopentanoate

  Catalysed by GLYATL2, AGXT2

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

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

• kynurenateReach from here →
  1. N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. L-kynurenine + glyoxylate = kynurenate + glycine + H2O

  Catalysed by PAM, KYAT3, AADAT

• L-2-aminohexanoateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by GLYATL2, AGXT2

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by GLYATL2, SHMT1, ATICcytosol

• 5-guanidino-2-oxopentanoateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of arginine and glycine (cytosol to extracellular)
  3. L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + H2O2 + NH4(+)

  Catalysed by GLYATL2, SLC7A6, IL4I1extracellular space, cytosol

• (3Z)-dodecenoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by GLYATL2, BAAT, HADHA, ACAA2 and 1 moreperoxisome, mitochondrial matrixOne of 5 routes

• S-sulfanyl-L-cysteineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

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

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by GLYATL2, AGPAT2, GPAT3, GPAT2 and 10 morecytosol

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

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

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

  Catalysed by GLYATL2, BAAT, SLC27A2, SLC27A5peroxisome, endoplasmic reticulumOne of 3 routes

• 5-phospho-beta-D-ribosylamineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

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

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

  Catalysed by GLYATL2, SLC7A5, GFPT2, GFPT1extracellular space, cytosol

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

  Catalysed by GLYATL2, SLC7A5, MSRAextracellular space, cytosol

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

  Catalysed by GLYATL2, SLC7A5, MSRB3, MSRB1 and 1 moreextracellular space, cytosol

• 5-amino-2-oxopentanoateReach from here →
  1. N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. L-ornithine + glyoxylate = 5-amino-2-oxopentanoate + glycine

  Catalysed by PAM, AGXT2One of 3 routes

• deoxycholoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by GLYATL2, BAAT, SLC27A2, SLC27A5peroxisome, cytosolOne of 4 routes

• S-sulfanylglutathioneReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by GLYATL2, GSS, SQORcytosol, mitochondrial matrixOne of 5 routes

• methylamineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  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 GLYATL2, AGXT2, DDAH1

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosolOne of 4 routes

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  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 GLYATL2, AADAT, PAH

• 4-aminobutanoateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of chloride and glycine (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by GLYATL2, SLC6A9, SLC6A14, SLC6A12extracellular space, cytosolOne of 4 routes

• 3-iodo-L-tyrosineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of glycine and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

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

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

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

• glycolithocholate 3-sulfateReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA:amino acid N-acyltransferase (glycine)
  3. sulfotransferase (glycolithocholate)

  Catalysed by GLYATL2, BAAT, SULT2A1cytosolOne of 3 routes

• L-prolineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  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 GLYATL2, SLC3A2, SLC7A5, SLC7A10 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• prostaglandin E2Reach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin E2 (cytosol to extracellular)

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

• 3-sulfino-L-alanineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by GLYATL2, SLC3A2, SLC7A5, SLC7A8 and 1 moreextracellular space, cytosolOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by GLYATL2, MECRcytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by GLYATL2, ACADM, ECHS1, ACAA2 and 2 moremitochondrial matrixOne of 5 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by GLYATL2, BAAT, CPT1A, CPT1C and 1 moreperoxisome, cytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 12 routes

• L-cysteinylglycineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. glutathione gamma-glutamylaminopeptidase

  Catalysed by GLYATL2, GSS, GGTLC3, GGT1 and 4 morecytosolOne of 8 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by PAM, HOGA1

• a cardiolipinReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by GLYATL2, HADHAcytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by GLYATL2, BAAT, CPT1A, CPT1Bperoxisome, cytosol

• leukotriene D4Reach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. leukotriene C4 hydrolysis
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by GLYATL2, GGT1, GGT5cytosol

• an all-trans-retinyl esterReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by GLYATL2, DGAT1, PNPLA4, AWAT2 and 1 morecytosol

• CHEBI:63544Reach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 8 routes

• ubiquinol-10Reach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10

  Catalysed by GLYATL2, GSS, SQOR

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by GLYATL2, LPCAT4, LPCAT3, MBOAT1 and 1 morecytosol

• a triacyl-sn-glycerolReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by GLYATL2, DGAT1, MOGAT2, AWAT2 and 3 morecytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. acyl-CoA pool formation and breakdown
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by GLYATL2, LCLAT1, LPCAT1, GPAMcytosol

• hexacosanoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

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

• tetracosanoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 11 routes

• docosanoyl-CoAReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 10 routes

• N-(tetradecanoyl)-sphinganineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by GLYATL2, CERS6, CERS5cytosol

• 3-oxohexadecasphinganineReach from here →
  1. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by GLYATL2, SPTLC1, SPTLC3cytosol

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

  Catalysed by GLYATL2, SLC7A6, NOS3, NOS1 and 1 moreextracellular space, cytosol

• xanthurenateReach from here →
  1. N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O

  Catalysed by PAM, KYAT3, AADAT