(S)-malate

Three steps

• CHEBI:27760Reach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. Selenocystathionine Lysteine-lyase (deaminating)

  Catalysed by ME2, ME3, AGXT2, CTHmitochondrial matrix, cytosol

• elaidic acidReach 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 (elaidate)

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

• (2-hydroxyphenyl)acetic acidReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. Phenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)

  Catalysed by CLYBL, AADAT, HPDcytosol

• 3-mercaptolactic acidReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 3-Mercaptolactate:NAD+ oxidoreductase

  Catalysed by ME2, ME3, MPST, LDHB and 3 moremitochondrial matrix, cytosol

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

  Catalysed by AGXT2mitochondrial matrix, cytosol

• CHEBI:28666Reach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. LTD4 hydrolysis

  Catalysed by CLYBL, AADATcytosol

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. dehydroepiandrosterone 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate + H(+)
  3. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase

  Catalysed by SLC25A10, STSmitochondrial matrix, cytosolOne of 3 routes

• CHEBI:28701Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by CS, ACAA1, SCP2, MYO5Bmitochondrial matrix, cytosol, peroxisomeOne of 7 routes

• 17alpha-hydroxypregnenoloneReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

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

• pyridoxine 5'-phosphateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by ME2, ME3, AGXT2, SCLYmitochondrial matrix, cytosol

• N-glycoloylneuraminateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  3. CMP-N-acetylneuraminate monooxygenase (N-acetylneuraminate)

  Catalysed by ME2, ME3, NPLmitochondrial matrix, cytosol

• a carboxylateReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by ME2, ME3, FAHD1mitochondrial matrix

• L-ascorbic acidReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. L-dehydroascorbate + 2 glutathione = glutathione disulfide + L-ascorbate

  Catalysed by SLC25A10, TSTD1, CLIC1, GSTO1 and 1 moremitochondrial matrix, cytosolOne of 7 routes

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

  Catalysed by GOT2, SLC1A7, SLC1A3, SLC1A2 and 2 moremitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• 3-methyl-1-hydroxybutylthiamine diphosphateReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
  3. branched chain keto acid dehydrogenase E1 (4-methyl-2-oxopentanoate)

  Catalysed by CLYBL, AADAT, BCKDHA, BCKDHBmitochondrial matrix

• Gly-tRNA(Gly)Reach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. glycine:tRNA(Gly) ligase (AMP-forming)

  Catalysed by CLYBL, AADAT, GARS1cytosol

• Asp-tRNA(Asp)Reach from here →
  1. transport of malate and OAA (cytosol to mitochondria)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. L-Aspartate:tRNA(Asp) ligase (AMP-forming)

  Catalysed by GOT2, DARS1mitochondrial matrix, cytosol

• a thiolReach from here →
  1. transport of malate and thiosulfate (cytosol to mitochondria)
  2. 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific) (H2S2O3)
  3. L-cysteinyl-[sulfatase] + 2 a thiol + O2 = an organic disulfide + 3-oxo-L-alanyl-[sulfatase] + hydrogen sulfide + H2O + H(+)

  Catalysed by SLC25A10, SUMF1mitochondrial matrix, cytosol

• glycocholateReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. glycocholate(in) + glutathione(in) + ATP + H2O = glycocholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLC25A10, TSTD1, ABCC4mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• cholateReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLC25A10, TSTD1, ABCC4mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membrane

• orotateReach from here →
  1. (S)-malate hydro-lyase (fumarate-forming)
  2. a quinone + succinate = fumarate + a quinol
  3. (S)-dihydroorotate + a quinone = orotate + a quinol

  Catalysed by FH, SDHB, DHODHcytosolOne of 2 routes

• (indol-3-yl)acetateReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. a dicarboxylate(in) + sulfate(out) = a dicarboxylate(out) + sulfate(in)
  3. (indol-3-yl)acetate(out) + a dicarboxylate(in) = (indol-3-yl)acetate(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

• an alcoholReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O

  Catalysed by SLC25A10, TSTD1, CP, PRDX6mitochondrial matrix, cytosol

• glutarateReach from here →
  1. Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2
  2. cis-aconitate carboxy-lyase
  3. itaconate + glutaryl-CoA = itaconyl-CoA + glutarate

  Catalysed by SLC25A1, ACOD1, SUGCTmitochondrial matrix, cytosolOne of 7 routes

• pentanoateReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. dehydroepiandrosterone 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate + H(+)
  3. pentanoate(out) + dehydroepiandrosterone 3-sulfate(in) = pentanoate(in) + dehydroepiandrosterone 3-sulfate(out)

  Catalysed by SLC25A10, STS, SLC22A9mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

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

  Catalysed by GOT2, CADmitochondrial matrix, cytosolOne of 2 routes

• methylarsonateReach from here →
  1. transport of malate and thiosulfate (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by SLC25A10, TSTD1, GSTO1, GSTO2mitochondrial matrix, cytosol

• 4-methylthio-2-oxobutanoic acidReach 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. L-Methionine:oxygen oxidoreductase (deaminating)

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

• a phenolReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. an aryl sulfate + H2O = a phenol + sulfate + H(+)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SLC25A10, ARSL, ARSF, ARSK and 3 moremitochondrial matrix, cytosol

• dodecanamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate

  Catalysed by CLYBL, PAM

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

  Catalysed by AGXT2mitochondrial matrix, cytosol

• D-cysteineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by ME2, ME3, AGXT2, SLC7A10mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by ME2, ME3, AGXT2, GPTmitochondrial matrix, cytosol

• 5-aminolevulinateReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. succinyl-CoA + glycine + H(+) = 5-aminolevulinate + CO2 + CoA

  Catalysed by CLYBL, AADAT, ALAS1, ALAS2

• glycochenodeoxycholateReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. glycochenodeoxycholate(in) + glutathione(in) + ATP + H2O = glycochenodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLC25A10, TSTD1, ABCC4mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• taurocholateReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. taurocholate(in) + glutathione(in) + ATP + H2O = taurocholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by SLC25A10, TSTD1, ABCC4mitochondrial matrix, cytosol, inner side of the membrane, outer side of the membrane

• glycochenodeoxycholic acidReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by CLYBL, AADAT, BAATperoxisomeOne of 3 routes

• 3-hydroxyisovaleric 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 decarboxylation

  Catalysed by CLYBL, AADAT, ALOX12B, ALOXE3cytosol

• glycolithocholic acidReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. bile acid-CoA:amino acid N-acyltransferase (glycine)

  Catalysed by CLYBL, AADAT, BAATcytosolOne of 2 routes

• decanamideReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate
  3. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate

  Catalysed by CLYBL, PAM

• L-2-amino-3-oxobutanoic acidReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. Acetyl-CoA:glycine C-acetyltransferase

  Catalysed by CLYBL, AADAT, GCATmitochondrial matrix

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

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

  Catalysed by ME2, ME3, HMGCL, HMGCLL1mitochondrial matrix, cytosol

• 13-cis-retinalReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. retinal dehydrogenase (13-cis-retinal)

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

• tert-butanolReach from here →
  1. transport of malate and sulfite (cytosol to mitochondria)
  2. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)
  3. tert-butyl hydroperoxide + 2 glutathione = tert-butanol + glutathione disulfide + H2O

  Catalysed by SLC25A10, TSTD1, CLIC2, GPX1 and 3 moremitochondrial matrix, cytosol

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

  Catalysed by ME2, ME3, AGXT2, SLC7A6mitochondrial matrix, extracellular space, cytosolOne of 12 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. (S)-malate:NAD+ oxidoreductase (decarboxylating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

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

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)
  2. glyoxylate + L-methionine = 4-methylsulfanyl-2-oxobutanoate + glycine
  3. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 4-methylsulfanyl-2-oxobutanoate + formate + 2 H(+)

  Catalysed by CLYBL, AADAT, ADI1

• (5-hydroxyindol-3-yl)acetaldehydeReach from here →
  1. transport of malate and sulfate (cytosol to mitochondria)
  2. Transport of 5-Hydroxyindoleacetate
  3. (5-hydroxyindol-3-yl)acetaldehyde + NAD(+) + H2O = (5-hydroxyindol-3-yl)acetate + NADH + 2 H(+)

  Catalysed by SLC25A10, SLC4A1, ALDH9A1mitochondrial matrix, cytosol, extracellular space

• gamma-Glu-AlaReach 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, GGT1 and 5 moremitochondrial matrix, extracellular space, cytosol