CHEBI:18019

Three steps

• fatty acidReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (elaidate)
  3. (10Z)-heptadecenoic acid formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 moremitochondrial matrix, cytosolOne of 4 routes

• L-alpha-aminobutyric acidReach from here →
  1. transport of lysine and threonine (cytosol to extracellular)
  2. L-threonine ammonia-lyase (2-oxobutanoate-forming)
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by SLC7A6, SDS, SDSL, GPTextracellular space, cytosol

• chenodeoxycholateReach from here →
  1. Acetylation of Lysine
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. chenodeoxycholoyl-CoA hydrolase

  Catalysed by ACAA1, SCP2, MYO5B, ACOT7 and 2 moremitochondrial matrix, peroxisomeOne of 3 routes

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

  Catalysed by SLC7A6, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 8 routes

• taurodeoxycholateReach from here →
  1. transport of chloride and lysine (cytosol to extracellular)
  2. Neurotransmitter:Sodium Symporter (Nss) Tcdb:2.A.22.3.3
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC6A14, SLC6A6, BAATextracellular space, cytosolOne of 4 routes

• 3-hydroxyanthranilateReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by SLC7A6, KYNUextracellular space, cytosol

• N-formylanthranilic acidReach from here →
  1. transport of lysine and tryptophan (cytosol to extracellular)
  2. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)
  3. Formylkynurenine hydrolase

  Catalysed by SLC7A6, IDO1, TDO2, IDO2 and 1 moreextracellular space, cytosol

• cholesteryl hexadecanoateReach from here →
  1. Acetylation of Lysine
  2. Palmitate:CoA ligase (AMP-forming)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• CHEBI:36882Reach from here →
  1. Acetylation of Lysine
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA hydro-lyase (itaconyl-CoA-forming)

  Catalysed by SUCLG1, SUCLG2, SUCLA2, AUHmitochondrial matrix

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

  Catalysed by SLC7A6, BCAT2, ALOX12B, ALOXE3extracellular space, cytosol, mitochondrial matrixOne of 2 routes

• 3,7,11,15-tetramethylhexadecanoateReach from here →
  1. Acetylation of Lysine
  2. phytanate-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by ACOT2mitochondrial matrix, cytosol, peroxisomeOne of 3 routes

• sphingosine 1-phosphateReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moremitochondrial matrix, Golgi apparatus, cytosolOne of 2 routes

• cholesteryl (9Z,12Z)-octadecadienoateReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• D-glucopyranose 6-phosphateReach from here →
  1. transport of citrulline and lysine (cytosol to extracellular)
  2. Carbamoyl-phosphate:L-ornithine carbamoyltransferase
  3. glucose-6-phosphatase (carbamoyl-phosphate)

  Catalysed by SLC7A5, SLC7A6, OTC, G6PC2extracellular space, cytosol, mitochondrial matrix, endoplasmic reticulum

• (R)-lactic acidReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (R)-Lactate:NAD+ oxidoreductase

  Catalysed by SLC7A6, AGXT2, LDHDextracellular space, cytosol, mitochondrial matrix

• (S)-lactic acidReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (S)-Lactate:NAD+ oxidoreductase

  Catalysed by SLC7A6, AGXT2, LDHB, LDHAL6Bextracellular space, cytosol, mitochondrial matrixOne of 7 routes

• 25-hydroxycholesterolReach 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. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by SLC7A6, MOCOS, CH25Hextracellular space, cytosol

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. Acetylation of Lysine
  2. Production of Glutaryl Carnitine
  3. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate

  Catalysed by CPT1A, CPT1C, CPT1B, SUGCTmitochondrial matrix, cytosol

• (6R)-L-erythro-6,7-dihydrobiopterinReach from here →
  1. transport of lysine and tryptophan (cytosol to extracellular)
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
  3. (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin = (6R)-L-erythro-6,7-dihydrobiopterin + H2O

  Catalysed by SLC7A6, TPH1, TPH2, PCBD1 and 1 moreextracellular space, cytosol

• 2-iminopropanoateReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 2-iminopropanoate + H2O = pyruvate + NH4(+)

  Catalysed by SLC7A6, AGXT2, RIDAextracellular space, cytosol, mitochondrial matrix

• phosphoenolpyruvic acidReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. pyruvate kinase (dTDP)

  Catalysed by SLC7A6, AGXT2, PKM, PKLRextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• 13-cis-retinolReach from here →
  1. Acetylation of Lysine
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 13-cis-retinol

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 moremitochondrial matrix, cytosol

• spermineReach from here →
  1. deoxyhypusine synthase (1,3-diaminopropane)
  2. deoxyhypusine synthase (1,3-diaminopropane)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + spermidine = spermine + S-methyl-5'-thioadenosine + H(+)

  Catalysed by DHPS, SMScytosolOne of 3 routes

• N-acetyl-beta-neuraminic acidReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by SLC7A6, AGXT2, NPLextracellular space, cytosol, mitochondrial matrix

• tert-butanolReach from here →
  1. transport of glycine and lysine (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 SLC7A6, GSS, CLIC2, GPX1 and 3 moreextracellular space, cytosol

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. Acetylation of Lysine
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, SOAT2 and 1 moremitochondrial matrix, cytosol, endoplasmic reticulum

• N-(acetyl)-sphing-4-enineReach 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 apparatusOne of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

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

• 2-methyl-1-hydroxypropylthiamine diphosphateReach from here →
  1. transport of lysine and valine (cytosol to extracellular)
  2. L-Valine:2-oxoglutarate aminotransferase
  3. branched chain keto acid dehydrogenase E1 (3-methyl-2-oxobutyrate)

  Catalysed by SLC7A6, BCAT2, BCKDHA, BCKDHBextracellular space, cytosol, mitochondrial matrix

• a 1,2-diacylglycerolReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 5 moremitochondrial matrix, Golgi apparatusOne of 2 routes

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. transport of lysine and methionine (cytosol to extracellular)
  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 SLC7A6, AADAT, ADI1extracellular space, cytosol

• all-trans-13,14-dihydroretinolReach 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. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by SLC7A6, MOCOS, RETSATextracellular space, cytosol

• an N-acylsphing-4-enineReach from here →
  1. Acetylation of Lysine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)

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

• N-tetracosanoylsphinganineReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. tetracosanoyl-CoA + sphinganine = N-tetracosanoylsphinganine + CoA + H(+)

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

• N-hexacosanoylsphinganineReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + sphinganine = N-hexacosanoylsphinganine + CoA + H(+)

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

• 3,3',5-triiodo-L-thyronineReach 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 triiodothyronine (cytosol to extracellular)

  Catalysed by SLC7A6, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 8 routes

• 3,3',5'-triiodo-L-thyronineReach 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. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by SLC7A6, MOCOS, DIO1, DIO3extracellular space, cytosol

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

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moremitochondrial matrix, Golgi apparatus

• a 3-acylpyruvateReach from here →
  1. transport of alanine and lysine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by SLC7A6, AGXT2, FAHD1extracellular space, cytosol, mitochondrial matrix

• succinyl-CoAReach from here →
  1. Acetylation of Lysine
  2. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)
  3. (R)-methylmalonyl-CoA = succinyl-CoA

  Catalysed by ALDH6A1, MMUTmitochondrial matrixOne of 3 routes

• (2E)-butenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 4 moremitochondrial matrix, cytosolOne of 4 routes

• 3-methyl-(2E)-glutaconyl-CoAReach from here →
  1. Acetylation of Lysine
  2. glycine-N-acyltransferase (3-methylcrotonoylglycine)
  3. 3-Methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)

  Catalysed by GLYAT, MCCC1, MCCC2mitochondrial matrixOne of 2 routes

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

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

• (2E)-glutaconyl-CoAReach from here →
  1. Acetylation of Lysine
  2. Production of Glutaryl Carnitine
  3. glutaryl-CoA + O2 = (2E)-glutaconyl-CoA + H2O2

  Catalysed by CPT1A, CPT1C, CPT1B, ACOX1mitochondrial matrix, cytosol

• acryloyl-CoAReach from here →
  1. Acetylation of Lysine
  2. Propanoate:CoA ligase (AMP-forming)
  3. medium-chain acyl-CoA dehydrogenase (propanoyl-CoA)

  Catalysed by ACSS3, ACSS2, ACSS1, ACADS and 1 moremitochondrial matrix, cytosol

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

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

  Catalysed by SLC7A6, GLYATextracellular space, cytosol, mitochondrial matrix

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

  Catalysed by SLC7A6, GLYATL3extracellular space, cytosolOne of 3 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. Acetylation of Lysine
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

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