CHEBI:18019

Three steps

• L-thyroxineReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and thyroxine (cytosol to extracellular)

  Catalysed by SLC7A6, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• kynurenateReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. L-kynurenine + glyoxylate = kynurenate + glycine + H2O

  Catalysed by SLC7A6, AADAT, KYAT3extracellular space, cytosolOne of 20 routes

• L-2-aminohexanoateReach from here →
  1. transport of arginine and lysine (cytosol to extracellular)
  2. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by SLC3A2, SLC7A5, SLC7A6, SLC25A2 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by SLC7A6, SHMT1, ATICextracellular space, cytosol

• N(8)-acetylspermidineReach from here →
  1. deoxyhypusine synthase (1,3-diaminopropane)
  2. deoxyhypusine synthase (1,3-diaminopropane)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by DHPScytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. Acetylation of Lysine
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  No catalyst recordedmitochondrial matrix, cytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 moremitochondrial matrix, cytosolOne of 2 routes

• N(tau)-methylhistamineReach from here →
  1. transport of histidine and lysine (cytosol to extracellular)
  2. L-histidine carboxy-lyase (histamine-forming)
  3. S-Adenosyl-L-methionine:histamine N-tele-methyltransferase

  Catalysed by SLC7A5, SLC7A6, HDC, HNMTextracellular space, cytosolOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 13 moremitochondrial matrix, Golgi apparatus

• (3S)-citramalyl-CoAReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by SLC7A6, AGXT2, CLYBLextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• L-2-aminoadipateReach from here →
  1. N6-(L-1,3-Dicarboxypropyl)-L-lysine:NADP+ oxidoreductase (L-lysine-forming)
  2. L-saccharopine + NAD(+) + H2O = (S)-2-amino-6-oxohexanoate + L-glutamate + NADH + H(+)
  3. (S)-2-amino-6-oxohexanoate + NAD(+) + H2O = L-2-aminoadipate + NADH + 2 H(+)

  Catalysed by AASS, ALDH7A1mitochondrial matrixOne of 2 routes

• phosphoenolpyruvateReach from here →
  1. Acetylation of Lysine
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by ACLY, PCK1, PCK2mitochondrial matrix, cytosol

• S-sulfanylglutathioneReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by SLC7A6, GSS, SQORextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• methylamineReach from here →
  1. transport of arginine and lysine (cytosol to extracellular)
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine

  Catalysed by SLC3A2, SLC7A5, SLC7A6, SLC25A29 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• monodehydro-L-ascorbate radicalReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  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 SLC7A6, GLYATL3, GLYATL2, PAMextracellular space, cytosolOne of 5 routes

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  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 SLC7A6, AADAT, PAHextracellular space, cytosolOne of 4 routes

• pyridoxal 5'-phosphateReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. pyridoxine 5'-phosphate + O2 = pyridoxal 5'-phosphate + H2O2

  Catalysed by SLC7A6, SCLY, PNPOextracellular space, cytosol

• 2-hydroxy-4-methylvaleric acidReach from here →
  1. transport of leucine and lysine (cytosol to extracellular)
  2. L-Leucine:2-oxoglutarate aminotransferase
  3. 4-methyl-2-oxopentanoate reduction

  Catalysed by SLC7A6, BCAT2, SDR42E2, AKR1B15 and 16 moreextracellular space, cytosol, mitochondrial matrix

• an L-alpha-amino acidReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. L-kynurenine + H2O = anthranilate + L-alanine + H(+)
  3. an L-alpha-amino acid(in) + L-kynurenine(out) = an L-alpha-amino acid(out) + L-kynurenine(in)

  Catalysed by SLC7A6, KYNU, SLC7A11extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by SLC7A6, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• glycolithocholate 3-sulfateReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. bile acid-CoA:amino acid N-acyltransferase (glycine)
  3. sulfotransferase (glycolithocholate)

  Catalysed by SLC7A6, BAAT, SULT2A1extracellular space, cytosolOne of 3 routes

• a 2,3-dehydroacyl-CoAReach from here →
  1. transport of cysteine and lysine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by SLC7A6, MOCOS, ACAD10extracellular space, cytosol

• estrone 3-sulfateReach from here →
  1. transport of chloride and lysine (cytosol to extracellular)
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. estrone 3-sulfate + H2O = estrone + sulfate + H(+)

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosol

• sphing-4-enine 1-phosphateReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moremitochondrial matrix, Golgi apparatus

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

  Catalysed by SLC7A6, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosolOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 moremitochondrial matrix, cytosolOne of 8 routes

• Fe(II)-heme aReach from here →
  1. transport of cysteine and lysine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by SLC7A6, MOCOS, COX15extracellular space, cytosol

• (R)-4'-phosphopantetheineReach from here →
  1. transport of cysteine and lysine (cytosol to extracellular)
  2. (R)-4'-phosphopantothenate:L-cysteine ligase
  3. N-[(R)-4-phosphopantothenoyl]-L-cysteine + H(+) = (R)-4'-phosphopantetheine + CO2

  Catalysed by SLC7A6, PPCS, PPCDCextracellular space, cytosol

• (2E)-hexenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. medium-chain acyl-CoA ligase (hexanoic acid)
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 moremitochondrial matrix, cytosolOne of 3 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by SLC7A6, AADAT, HOGA1extracellular space, cytosolOne of 2 routes

• a cardiolipinReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 1 moremitochondrial matrix, Golgi apparatus

• (2E)-octenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by CROT, MECRmitochondrial matrixOne of 5 routes

• 3-oxotetradecanoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + malonyl-CoA + H(+) = 3-oxotetradecanoyl-CoA + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylateReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. Transport of Hydroxy-Proline
  3. trans-4-Hydroxy-L-proline:NAD+ 5-oxidoreductase

  Catalysed by SLC7A6, SLC1A4, PYCR1, PYCR3 and 1 moreextracellular space, cytosolOne of 5 routes

• (5-hydroxyindol-3-yl)acetateReach from here →
  1. transport of chloride and lysine (cytosol to extracellular)
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. Transport of 5-Hydroxyindoleacetate

  Catalysed by SLC6A14, SLC26A6, SLC4A1extracellular space, cytosolOne of 2 routes

• 2-deoxy-D-ribose 5-phosphateReach from here →
  1. transport of lysine and threonine (cytosol to extracellular)
  2. L-threonine acetaldehyde-lyase (glycine-forming)
  3. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde

  Catalysed by SLC7A6, DERAextracellular space, cytosol

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

  Catalysed by SLC7A6, GGT1, GGT5extracellular space, cytosol

• an all-trans-retinyl esterReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moremitochondrial matrix, Golgi apparatusOne of 4 routes

• ubiquinol-10Reach from here →
  1. transport of glycine and lysine (cytosol to extracellular)
  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 SLC7A6, GSS, SQORextracellular space, cytosolOne of 3 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moremitochondrial matrix, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moremitochondrial matrix, Golgi apparatus

• a triacyl-sn-glycerolReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 6 moremitochondrial matrix, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 3 moremitochondrial matrix, Golgi apparatus

• 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phospho-D-myo-inositol + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 moremitochondrial matrix, cytosol

• 3-oxoeicosasphinganineReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + L-serine + H(+) = 3-oxoeicosasphinganine + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moremitochondrial matrix, cytosol

• a 2,3-saturated acyl-CoAReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by SLC7A6, MOCOS, ACAD10extracellular space, cytosol

• 3-oxoeicosanoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 moremitochondrial matrix, cytosolOne of 2 routes

• N-docosanoylsphinganineReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + sphinganine = N-docosanoylsphinganine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 moremitochondrial matrix, cytosol