CHEBI:1146900

Three steps

• decanalReach from here →
  1. medium-chain acyl-CoA ligase (decanoic acid)
  2. Decanoyl-CoA hydrolase
  3. decanal + NAD(+) + H2O = decanoate + NADH + 2 H(+)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 4 morecytosol

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. sphingosine N-acyltransferase (sphinganine)
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 8 moreGolgi apparatus, cytosolOne of 3 routes

• L-lysineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. L-ornithine(out) + L-lysine(in) = L-ornithine(in) + L-lysine(out)

  Catalysed by BAAT, GATM, SLC25A2, SLC25A15cytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• D-lysineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by BAAT, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-arginineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by BAAT, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• cis-aconitic acidReach from here →
  1. ATP citrate lyase (citrate)
  2. transport of malate and OAA (cytosol to mitochondria)
  3. Mitochondrial Carrier (Mc) Tcdb:2.A.29.7.2

  Catalysed by ACLY, SLC25A1cytosol, mitochondrial matrixOne of 8 routes

• N-carbamoyl-L-aspartateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. carbamoyl phosphate + L-aspartate = N-carbamoyl-L-aspartate + phosphate + H(+)

  Catalysed by AGXT2, CADmitochondrial matrix

• 3-oxopropanoateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 3-oxopropanoate + L-alanine = beta-alanine + pyruvate

  Catalysed by AGXT2mitochondrial matrixOne of 2 routes

• thiosulfateReach from here →
  1. ATP citrate lyase (citrate)
  2. transport of malate and OAA (cytosol to mitochondria)
  3. transport of malate and thiosulfate (cytosol to mitochondria)

  Catalysed by ACLY, SLC25A10cytosol, mitochondrial matrixOne of 6 routes

• tetra-mu3-sulfido-tetrairon(2+)Reach from here →
  1. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  2. De novo synthesis of 2Fe2S
  3. Synthesis of 4Fe4S from 2Fe2S

  Catalysed by NAGS, NDUFAB1, FDXR, FXN and 10 moremitochondrial matrix

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. glycerol-3-phosphate 1-O-acyltransferase (arachidonyl-CoA)
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + phosphate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

• 1-O-hexadecyl-sn-glycerolReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. 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(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + H2O = 1-O-hexadecyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus

• serotoninReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and serotonin (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 31 morecytosol, extracellular spaceOne of 5 routes

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

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A5 and 2 moremitochondrial matrix, extracellular space, cytosol

• 2-oxohexanoateReach from here →
  1. ATP citrate lyase (citrate)
  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 ACLY, AGXT2cytosol

• L-alpha-aminobutyric acidReach from here →
  1. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  2. L-cystathionine cysteine-lyase (deaminating
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by NAGS, CTH, GPTmitochondrial matrix, cytosol

• a 1-acylglycerolReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA
  3. a 1,2-diacylglycerol + H2O = a 1-acylglycerol + a fatty acid + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 6 moreGolgi apparatusOne of 2 routes

• a sterol esterReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. a sterol + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sterol ester + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus

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

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A5 and 1 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• 12-hydroxydodecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

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

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A5 and 3 moremitochondrial matrix, extracellular space, cytosolOne of 7 routes

• (R)-mevalonateReach from here →
  1. Production of Glutaryl Carnitine
  2. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate
  3. (R)-mevalonate + 2 NADP(+) + CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + 2 NADPH + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SUGCT and 1 morecytosol

• 3-hydroxyanthranilateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by KYNUmitochondrial matrix

• (R)-lactic acidReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (R)-Lactate:NAD+ oxidoreductase

  Catalysed by AGXT2, LDHDmitochondrial matrix, cytosol

• (S)-lactic acidReach from here →
  1. Propanoate:CoA ligase (AMP-forming)
  2. Propanoyl-CoA hydrolase
  3. transport of L-lactate and propanoate (cytosol to extracellular)

  Catalysed by ACSS3, ACSS2, ACSS1, ACOT7 and 6 morecytosol, extracellular spaceOne of 9 routes

• 25-hydroxycholesterolReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by BAAT, MTO1, CH25Hcytosol

• 2-iminopropanoateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 2-iminopropanoate + H2O = pyruvate + NH4(+)

  Catalysed by AGXT2, RIDAmitochondrial matrix

• all-trans-4-oxoretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. cytochrome P450 (retinol)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol

• 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. 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(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + acetyl-CoA = 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatus

• 13-cis-retinalReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 13-cis-retinol
  3. retinol dehydrogenase (13-cis-retinal)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosolOne of 3 routes

• N-acetyl-beta-neuraminic acidReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by AGXT2, NPLmitochondrial matrix, cytosol

• tert-butanolReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  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 GLYAT, GLYATL2, GLYATL1, GSS and 5 moremitochondrial matrix

• 2,6,10,14-tetramethylpentadecanalReach from here →
  1. fatty-acid-CoA ligase
  2. peroxisomal acyl-CoA thioesterase
  3. Long-Chain-Aldehyde Dehydrogenase

  Catalysed by SLC27A2, ACOT2, ALDH3A2cytosol, peroxisomeOne of 2 routes

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. N-acetylglutamate synthase (N-acetylmethionine)
  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 NAGS, AADAT, ADI1mitochondrial matrix

• all-trans-13,14-dihydroretinolReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by BAAT, MTO1, RETSATcytosolOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 2 routes

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. fatty acid amide hydrolase (2-arachidonoylglycerol)

  Catalysed by CPT1A, CPT1C, CPT1B, FAAHcytosol, endoplasmic reticulum

• O-propanoyl-(R)-carnitineReach from here →
  1. (S)-methylmalonyl-CoA hydrolase
  2. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2
  3. propanoyl-CoA + (R)-carnitine = O-propanoyl-(R)-carnitine + CoA

  Catalysed by ECHDC1, CRATmitochondrial matrix

• 3,3',5-triiodo-L-thyronineReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and triiodothyronine (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 31 morecytosol, extracellular spaceOne of 5 routes

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, DGAT1 and 4 morecytosol, endoplasmic reticulumOne of 4 routes

• 16-hydroxyhexadecanoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by CPT1A, CPT1C, CPT1B, CYP4F2 and 1 morecytosol, endoplasmic reticulumOne of 2 routes

• 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. (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
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 3 routes

• 3,3',5'-triiodo-L-thyronineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by BAAT, MTO1, DIO1, DIO3cytosol

• a 6-(N-acetyl-alpha-D-glucosaminyl)-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + UDP-N-acetyl-alpha-D-glucosamine = a 6-(N-acetyl-alpha-D-glucosaminyl)-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositol + UDP + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatus

• a 3-acylpyruvateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by AGXT2, FAHD1mitochondrial matrix

• acetoacetyl-CoAReach from here →
  1. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)
  2. (R)-methylmalonyl-CoA = succinyl-CoA
  3. acetoacetate + succinyl-CoA = acetoacetyl-CoA + succinate

  Catalysed by ALDH6A1, MMUT, OXCT1mitochondrial matrix

• (3S)-3-hydroxybutanoyl-CoAReach from here →
  1. Butanoate:CoA ligase (AMP-forming)
  2. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase
  3. (S)-3-hydroxybutanoyl-CoA hydro-lyase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• (S)-malyl-CoAReach from here →
  1. ATP citrate lyase (citrate)
  2. transport of malate and OAA (cytosol to mitochondria)
  3. (S)-malate + ATP + CoA = (S)-malyl-CoA + ADP + phosphate

  Catalysed by ACLY, SUCLG1, SUCLA2cytosol, mitochondrial matrix