(S)-malate

Three steps

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by GOT2, AGAmitochondrial matrix, cytosol

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

  Catalysed by GOT2, SLC7A13mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 28 routes

• 3-hydroxy-L-kynurenineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by ME2, ME3, AGXT2, KYNUmitochondrial matrix

• L,L-cystathionineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by CS, NAGSmitochondrial matrix, cytosol

• 3',5'-cyclic AMPReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. 3',5'-cyclic AMP(out) + a dicarboxylate(in) = 3',5'-cyclic AMP(in) + a dicarboxylate(out)

  Catalysed by SLC25A10, SLC25A35, SLC25A34, SLC22A6mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-homocysteineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by ME2, ME3, TYW1B, TYW1 and 1 moremitochondrial matrix

• S-methyl-L-methionineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by ME2, ME3, TYW1B, TYW1 and 1 moremitochondrial matrix

• N-acetylputrescineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 4 moremitochondrial matrix, extracellular space, cytosol

• (2R)-2-phosphoglycerateReach from here →
  1. Citrate Transport, Mitochondrial
  2. transport of citrate and PEP (cytosol to mitochondria)
  3. 2-phospho-D-glycerate hydro-lyase (phosphoenolpyruvate-forming)

  Catalysed by SLC25A1, ENO1, ENO2, ENO3mitochondrial matrix, cytosolOne of 2 routes

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

  Catalysed by GOT2, SLC7A13mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 5 routes

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by GOT2, AGXT2mitochondrial matrix, cytosolOne of 9 routes

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

  Catalysed by CS, ASAH1, ACER2, ACER1 and 1 moremitochondrial matrix, cytosol, Golgi apparatusOne of 2 routes

• 5-oxo-L-prolineReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. glutathione = L-cysteinylglycine + 5-oxo-L-proline

  Catalysed by SLC25A10, TSTD1, CHAC2, CHAC1mitochondrial matrix, cytosol

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. (S)-malate hydro-lyase (fumarate-forming)
  2. 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole AMP-lyase
  3. 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole AMP-lyase

  Catalysed by FH, ADSLcytosolOne of 2 routes

• N(8)-acetylspermidineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 4 moremitochondrial matrix, extracellular space, cytosol

• (3Z)-dodecenoyl-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-oxomyrist-5-enoyl-CoA)

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

• (S)-3-amino-2-methylpropanoateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-3-amino-isobutanoate:2-oxoglutarate aminotransferase

  Catalysed by ME2, ME3, AGXT2, ABATmitochondrial matrix

• L-2-aminoadipateReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. L-2-aminoadipate + glyoxylate = 2-oxoadipate + glycine
  3. 2-oxoadipate + L-kynurenine = L-2-aminoadipate + kynurenate + H2O

  Catalysed by CLYBL, AADAT

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by CS, SLC27A2, SLC27A5mitochondrial matrix, cytosol, endoplasmic reticulumOne of 3 routes

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by ME2, ME3, SLC16A4, SLC16A5 and 4 moremitochondrial matrix, extracellular space, cytosol

• D-glucosamineReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate
  3. N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate

  Catalysed by SLC25A10, SGSHmitochondrial matrix, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by ME2, ME3, TYW1B, TYW1 and 1 moremitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by ME2, ME3, TYW1B, TYW1 and 3 moremitochondrial matrix

• deoxycholoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by CS, SLC27A2, SLC27A5mitochondrial matrix, cytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by CLYBL, AADAT, GLYATL2One of 2 routes

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(out) + a dicarboxylate(in) = (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(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

• 2-hydroxy-4-methylvaleric acidReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
  3. 4-methyl-2-oxopentanoate reduction

  Catalysed by CLYBL, AADAT, SDR42E2, AKR1B15 and 16 morecytosol

• 4-aminobutanoateReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by SLC25A10, SLC26A6, SLC6A12mitochondrial matrix, cytosol, extracellular spaceOne of 4 routes

• (2S)-2-phospholactateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (2S)-2-phospholactate + H2O = (S)-lactate + phosphate

  Catalysed by ME2, ME3, LDHA, LDHB and 4 moremitochondrial matrixOne of 2 routes

• prostaglandin E2Reach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. prostaglandin E2(out) + 2 (S)-lactate(in) = prostaglandin E2(in) + 2 (S)-lactate(out)

  Catalysed by ME2, ME3, LDHA, LDHB and 4 moremitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 4 routes

• N-benzoylglycineReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. N-benzoylglycine(out) + a dicarboxylate(in) = N-benzoylglycine(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 4 routes

• 3-sulfino-L-alanineReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. transport of 3-sulfinoalanine and aspartate (cytosol to mitochondria)

  Catalysed by GOT2, SLC25A12, SLC25A13mitochondrial matrix, cytosolOne of 4 routes

• decanoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by CS, ACSM4, ACSM1, ACSM2A and 3 moremitochondrial matrix, cytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Carnitine O-Palmitoyltransferase

  Catalysed by CS, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

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

• L-cysteinylglycineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. gamma-glutamyltransferase (alanine)

  Catalysed by ME2, ME3, AGXT2, GGTLC3 and 5 moremitochondrial matrix, cytosolOne of 4 routes

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

  Catalysed by CS, CPT1A, CPT1Bmitochondrial matrix, cytosol

• (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylateReach from here →
  1. (S)-malate hydro-lyase (fumarate-forming)
  2. a quinone + succinate = fumarate + a quinol
  3. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)

  Catalysed by FH, SDHB, PRODH2cytosolOne of 2 routes

• dTMPReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. pyruvate kinase (dTDP)
  3. DTDP Diphosphohydrolase

  Catalysed by ME2, ME3, PKM, PKLR and 3 moremitochondrial matrix, cytosol, extracellular spaceOne of 5 routes

• CHEBI:63544Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 7 routes

• 3-demethylubiquinol-10Reach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. ubiquinone-10 + hydrogen sulfide + sulfite + 2 H(+) = ubiquinol-10 + thiosulfate
  3. 3-demethylubiquinol-10 + S-adenosyl-L-methionine = ubiquinol-10 + S-adenosyl-L-homocysteine + H(+)

  Catalysed by SLC25A10, SQOR, COQ3mitochondrial matrix, cytosol

• hexacosanoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

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

• tetracosanoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 10 routes

• docosanoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 9 routes

• Mo-molybdopterinReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by ME2, ME3, AGXT2, MOCOSmitochondrial matrix

• (2E)-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

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 8 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 6 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by CS, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 7 routes