CHEBI:15570

Three steps

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

  Catalysed by SLC7A5, BCAT2, BCAT1cytosol, extracellular space

• 2-oxohexanoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by DAO, AGXT2peroxisome

• L-alpha-aminobutyric acidReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by DAO, AGXT2, GPTperoxisome, cytosol

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

  Catalysed by SLC7A5, BCAT1cytosol, extracellular spaceOne of 2 routes

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

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

• taurocholateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (GSH)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1A2 and 1 moreextracellular space, cytosolOne of 3 routes

• 3-hydroxyanthranilateReach from here →
  1. alanine racemase
  2. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by KYNUcytosol

• D-glucopyranose 6-phosphateReach from here →
  1. transport of D-alanine and glutamine (cytosol to extracellular)
  2. HCO3-:L-glutamine amido-ligase (ADP-forming, carbamate-phosphorylating)
  3. glucose-6-phosphatase (carbamoyl-phosphate)

  Catalysed by SLC3A2, SLC7A10, CAD, G6PC2extracellular space, cytosol, endoplasmic reticulum

• 25-hydroxycholesterolReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by MOCOS, CH25Hcytosol

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by DAO, HMGCL, HMGCLL1peroxisome, mitochondrial matrix, cytosol

• 13-cis-retinalReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. retinal dehydrogenase (13-cis-retinal)

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 5 moreperoxisome, extracellular space, cytosol, endoplasmic reticulum

• tert-butanolReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  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 SLC3A2, SLC7A10, GSS, CLIC2 and 4 moreextracellular space, cytosol

• N-(acetyl)-sphing-4-enineReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 3 moreperoxisome, extracellular space, cytosol

• taurineReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by BAATcytosol, mitochondrial matrixOne of 4 routes

• all-trans-13,14-dihydroretinolReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by MOCOS, RETSATcytosol

• 3,3',5-triiodo-L-thyronineReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3,3',5-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by MOCOS, DIO1, DIO2cytosolOne of 3 routes

• 3,3',5'-triiodo-L-thyronineReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by MOCOS, DIO1, DIO3cytosol

• acetoacetyl-CoAReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate

  Catalysed by DAO, AACSperoxisome, mitochondrial matrix, cytosolOne of 2 routes

• (S)-malyl-CoAReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. (S)-malate + ATP + CoA = (S)-malyl-CoA + ADP + phosphate

  Catalysed by DAO, ME2, SUCLG1, SUCLA2peroxisome

• (R)-methylmalonyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by ALDH6A1cytosol, mitochondrial matrixOne of 3 routes

• (S)-methylmalonyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (S)-methylmalonyl-CoA hydrolase

  No catalyst recordedcytosol, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by ACP2cytosol, mitochondrial matrix, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (2E)-dodecenoyl-CoA formation

  No catalyst recordedcytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by ACAA1, MYO5Bcytosol, mitochondrial matrix, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 7 routes

• benzoyl-CoAReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. Hippurate (Benzoylglycinate) Formation
  3. benzoyl-CoA + glycine = N-benzoylglycine + CoA + H(+)

  Catalysed by SLC3A2, SLC7A10, GLYATextracellular space, cytosol, mitochondrial matrix

• butanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 2 morecytosol, mitochondrial matrixOne of 11 routes

• dodecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 10 routes

• glutaryl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Glutaryl Carnitine

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrixOne of 2 routes

• hexadecanoyl-CoAReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by SLC3A2, SLC7A10, GLYATL3extracellular space, cytosol

• eicosanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 12 routes

• itaconyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Itaconate:CoA ligase (GDP-forming)

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

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 14 routes

• tetradecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 12 routes

• octanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by CROTcytosol, mitochondrial matrixOne of 21 routes

• phytanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. phytanate-CoA ligase

  No catalyst recordedcytosol, mitochondrial matrixOne of 5 routes

• propanoyl-CoAReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine
  3. 2-methyl-3-oxopropanoate + NAD(+) + CoA + H2O = propanoyl-CoA + hydrogencarbonate + NADH + H(+)

  Catalysed by DAO, AGXT2, ALDH6A1peroxisome

• octadecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 3 morecytosol, mitochondrial matrixOne of 15 routes

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

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 4 routes

• prostaglandin I2Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin I2 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• prostaglandin F2alphaReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 4 routes

• prostaglandin H2Reach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O

  Catalysed by MOCOS, PTGS1, PTGS2cytosolOne of 6 routes

• prostaglandin D2Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin D2 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 4 routes

• (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + AH2 = (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by MOCOS, TBXAS1, PTGS2, PTGIScytosolOne of 3 routes

• 7,8-dihydrofolateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. 5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase

  Catalysed by SLC3A2, SLC7A10, SHMT1, DHFR and 1 moreextracellular space, cytosolOne of 3 routes

• 5-formimidoyltetrahydrofolateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. 5-Formiminotetrahydrofolate:L-glutamate N-formiminotransferase

  Catalysed by SLC3A2, SLC7A10, SHMT1, FTCDextracellular space, cytosolOne of 2 routes

• leukotriene A4Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and leukotriene A4 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 3 routes

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. alanine racemase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by SLC7A6, ASLcytosol, extracellular spaceOne of 6 routes

• (R)-S-lactoylglutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)

  Catalysed by SLC3A2, SLC7A10, GSS, GLO1 and 1 moreextracellular space, cytosolOne of 3 routes

• carnosineReach from here →
  1. alanine racemase
  2. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)
  3. beta-alanine + L-histidine + ATP = carnosine + ADP + phosphate + H(+)

  Catalysed by SLC7A10, CARNS1cytosol, inner side of the membrane, outer side of the membrane