(S)-malate

Three steps

• tetradecamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  3. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate

  Catalysed by CLYBL, PAM

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + glutathione = (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

  Catalysed by SLC25A10, TSTD1, GSTM4, LTC4Smitochondrial matrix, cytosol

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 7 moremitochondrial matrix, extracellular space, cytosol, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 29 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• a phenyl acetateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 6 moremitochondrial matrix, extracellular space, cytosol

• S-methyl glutathioneReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. apo-[alkylcobalamin reductase] + methylcob(III)alamin + glutathione = S-methyl glutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by SLC25A10, TSTD1, MMACHCmitochondrial matrix, cytosol

• N(2)-(1-hydroxy-2-oxoethyl)-dGTPReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycolate + NADP(+) = glyoxylate + NADPH + H(+)
  3. N(2)-(1-hydroxy-2-oxoethyl)-dGTP + H2O = dGTP + glycolate + H(+)

  Catalysed by CLYBL, GRHPR, PARK7

• N(2)-(1-hydroxy-2-oxoethyl)-GMPReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycolate + NADP(+) = glyoxylate + NADPH + H(+)
  3. N(2)-(1-hydroxy-2-oxoethyl)-GMP + H2O = glycolate + GMP + H(+)

  Catalysed by CLYBL, GRHPR, PARK7

• N-hexadecanoylglycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL3

• N-dodecanoylglycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2One of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoylglycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate
  3. N-(9Z,12Z,15Z)-octadecatrienoylglycine + 2 L-ascorbate + O2 = N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by CLYBL, PAM

• N-decanoylglycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2One of 2 routes

• N-octanoylglycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2One of 2 routes

• octanamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-octanoyl-(2S)-hydroxyglycine = octanamide + glyoxylate
  3. N-octanoyl-(2S)-hydroxyglycine = octanamide + glyoxylate

  Catalysed by CLYBL, PAM

• (9Z,12Z,15Z)-octadecatrienamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate
  3. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate

  Catalysed by CLYBL, PAM

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

  Catalysed by CLYBL, AADAT, GART

• L-cystine-bis-glycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by CLYBL, AADAT, DPEP1, DPEP2

• indoxyl sulfateReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. indoxyl sulfate(out) + a dicarboxylate(in) = indoxyl sulfate(in) + a dicarboxylate(out)

  Catalysed by SLC25A10, SLC25A35, SLC25A34, SLC22A6 and 1 moremitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• glycyldehydrophenylalanineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by CLYBL, AADAT, DPEP1

• S-adenosylglutathioneReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. apo-[alkylcobalamin reductase] + adenosylcob(III)alamin + glutathione = S-adenosylglutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by SLC25A10, TSTD1, MMACHCmitochondrial matrix, cytosol

• an N-(fatty acyl)-glycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2

• (7Z)-octadecenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by CS, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 3 routes

• CHEBI:15345Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by CS, AACSmitochondrial matrix, cytosolOne of 5 routes

• acetoneReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. Acetoacetate carboxy-lyase (acetone-forming)

  Catalysed by ME2, ME3mitochondrial matrix, cytosol

• cholineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by CS, CHATmitochondrial matrix, cytosol, nucleusOne of 2 routes

• CHEBI:15380Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by CS, ALAS1, CPNE7mitochondrial matrix, cytosolOne of 8 routes

• CHEBI:15477Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by CS, GLYAT, GLYATL2, GLYATL1mitochondrial matrix, cytosolOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Production of Tiglylcarnitine

  Catalysed by CS, CPT1A, CPT1Bmitochondrial matrix, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by CS, HADHA, ACAA2, HADHBmitochondrial matrix, cytosolOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by CS, GLYATmitochondrial matrix, cytosol

• isovaleryl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by CS, GLYAT, GLYATL2, GLYATL1mitochondrial matrix, cytosolOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• CHEBI:15519Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. propanoyl-CoA C-acyltransferase

  Catalysed by CS, ACAA1, SCP2, MYO5Bmitochondrial matrix, cytosol, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• oleoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by CS, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 11 routes

• phenylacetyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Phenylacetate:CoA ligase

  Catalysed by CSmitochondrial matrix, cytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by CS, ACSS3, ACSS2, ACSS1mitochondrial matrix, cytosolOne of 48 routes

• CHEBI:15570Reach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. alanine racemase

  Catalysed by ME2, ME3, AGXT2mitochondrial matrix, cytosolOne of 3 routes

• L-leucineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. L-leucine(out) + L-aspartate(in) = L-leucine(in) + L-aspartate(out)

  Catalysed by GOT2, SLC7A13mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 21 routes

• CHEBI:15611Reach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by CLYBL, AADAT, GNMTcytosol

• 15(S)-HPETEReach from here →
  1. transport of malate and thiosulfate (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by SLC25A10, TSTD1, GPX5, GPX1 and 7 moremitochondrial matrix, cytosol

• 10-formyltetrahydrofolic acidReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 4 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• CHEBI:15650Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by CS, ZDHHC11B, NAA10, ESCO2 and 29 moremitochondrial matrix, cytosolOne of 2 routes

• CHEBI:15699Reach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and homoserine (cytosol to extracellular)

  Catalysed by ME2, ME3, AGXT2, SLC7A5mitochondrial matrix, extracellular space, cytosolOne of 10 routes

• CHEBI:15727Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by CS, NAA10mitochondrial matrix, cytosol

• formateReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. oxalate(in) + sulfate(out) = oxalate(out) + sulfate(in)
  3. oxalate(in) + formate(out) = oxalate(out) + formate(in)

  Catalysed by SLC25A10, SLC25A14, SLC26A2, SLC25A30 and 2 moremitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:15746Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by CS, SAT1, SAT2mitochondrial matrix, cytosolOne of 2 routes

• nicotinic acid D-ribonucleotideReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. Transport of Quinolinic Acid
  3. Nicotinate-nucleotide:pyrophosphate phosphoribosyltransferase (carboxylating)

  Catalysed by SLC25A10, SLC22A6, QPRTmitochondrial matrix, cytosol, extracellular space

• N-carbamoyl-L-aspartic acidReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. carbamoyl-phosphate:L-aspartate carbamoyltransferase

  Catalysed by GOT2, CADmitochondrial matrix, cytosolOne of 2 routes