CHEBI:16566

Three steps

• eicosanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. Eicosanoyl-CoA hydrolase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 13 morecytosolOne of 16 routes

• (9Z)-hexadecenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, endoplasmic reticulumOne of 20 routes

• (15Z)-tetracosenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (nervonic acid)
  3. (15Z)-tetracosenoyl-CoA hydrolase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosolOne of 13 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, endoplasmic reticulumOne of 16 routes

• (11Z)-eicosenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)
  3. (11Z)-eicosenoyl-CoA hydrolase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 13 morecytosolOne of 13 routes

• putrescineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosolOne of 3 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrix

• di-mu-sulfido-diiron(2+)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. De novo synthesis of 2Fe2S

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol, mitochondrial matrix

• D-cysteineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 3 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-serineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 3 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 6 routes

• an acylcholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Acetyl-CoA:choline O-acetyltransferase
  3. an acylcholine + H2O = a carboxylate + choline + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, nucleus

• 5-aminolevulinateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA + glycine + H(+) = 5-aminolevulinate + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, mitochondrial matrix

• a fatty aldehydeReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. an N-acylsphinganine + H2O = sphinganine + a fatty acid
  3. a fatty aldehyde + NAD(+) + H2O = a fatty acid + NADH + 2 H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol

• chenodeoxycholateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. chenodeoxycholoyl-CoA hydrolase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol, peroxisomeOne of 3 routes

• glycochenodeoxycholateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrix

• taurocholateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. propanoyl-CoA C-acyltransferase
  3. Choloyl-CoA:glycine N-choloyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, peroxisomeOne of 5 routes

• taurodeoxycholateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosolOne of 4 routes

• glycochenodeoxycholic acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, peroxisomeOne of 5 routes

• cholesteryl hexadecanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Palmitate:CoA ligase (AMP-forming)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, endoplasmic reticulum

• glyoxylateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine + 2-oxoglutarate = glyoxylate + L-glutamate

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrixOne of 11 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol, Golgi apparatus

• CHEBI:36882Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA hydro-lyase (itaconyl-CoA-forming)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrix

• 3-hydroxyisovaleric acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)
  3. Formation of 3-Hydroxy-Isovalerate

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrix

• 3,7,11,15-tetramethylhexadecanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. phytanate-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 3 morecytosol, peroxisomeOne of 3 routes

• sphingosine 1-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, Golgi apparatusOne of 2 routes

• glycolithocholic acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. bile acid-CoA:amino acid N-acyltransferase (glycine)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrixOne of 2 routes

• L-2-amino-3-oxobutanoic acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Acetyl-CoA:glycine C-acetyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrix

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

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, endoplasmic reticulumOne of 2 routes

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

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol

• phosphoenolpyruvic acidReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. ATP citrate lyase (citrate)
  3. GTP:oxaloacetate carboxy-lyase (adding GTP

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosolOne of 2 routes

• 13-cis-retinolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 13-cis-retinol

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol

• spermineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + spermidine = spermine + S-methyl-5'-thioadenosine + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosolOne of 2 routes

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

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, endoplasmic reticulum

• L-ornithineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosolOne of 15 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  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 CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatusOne of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol, Golgi apparatus

• a 1,2-diacylglycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol, Golgi apparatusOne of 2 routes

• gamma-Glu-AlaReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol, mitochondrial matrix, extracellular space

• S(8)-aminomethyldihydrolipoamideReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. dihydrolipoyl dehydrogenase ([protein]-N6-(lipoyl)lysine)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, mitochondrial matrix

• N-(2-hydroxytetracosanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. 2-hydroxytetracosanoyl-CoA + sphinganine = N-(2-hydroxytetracosanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 3 morecytosol

• N-tetracosanoylsphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. tetracosanoyl-CoA + sphinganine = N-tetracosanoylsphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 4 morecytosolOne of 2 routes

• N-hexacosanoylsphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. hexacosanoyl-CoA + sphinganine = N-hexacosanoylsphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 4 morecytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  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 CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, Golgi apparatus

• succinyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)
  3. (R)-methylmalonyl-CoA = succinyl-CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrixOne of 3 routes

• (2E)-butenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol, mitochondrial matrixOne of 4 routes

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

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• 3-oxohexadecanoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + malonyl-CoA + H(+) = 3-oxohexadecanoyl-CoA + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol

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

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol

• acryloyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Propanoate:CoA ligase (AMP-forming)
  3. medium-chain acyl-CoA dehydrogenase (propanoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, mitochondrial matrix

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  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 CERS1, CERS6, CERS3, CERS5 and 11 morecytosol