CHEBI:16566

Three steps

• 2,6,10,14-tetramethylpentadecanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. fatty-acid-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

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

• a 1,3-diacyl-sn-glycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 3-acyl-sn-glycerol + an acyl-CoA = a 1,3-diacyl-sn-glycerol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatusOne of 3 routes

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA

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

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus

• 1-O-(1Z)-alkenyl-2-octanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + octanoyl-CoA = 1-O-(1Z)-alkenyl-2-octanoyl-sn-glycero-3-phosphoethanolamine + CoA

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

• 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

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

• tetracosan-1-olReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. tetracosanoyl-CoA + 2 NADPH + 2 H(+) = tetracosan-1-ol + 2 NADP(+) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• (2E,9Z)-hexadecadienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. medium-chain acyl-CoA dehydrogenase (palmitoleoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol, mitochondrial matrixOne of 3 routes

• trans-2-heptadecenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (margaric acid)
  3. medium-chain acyl-CoA dehydrogenase (heptadecanoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol, mitochondrial matrixOne of 2 routes

• (2E,9Z)-octadecadienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. medium-chain acyl-CoA dehydrogenase (oleoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• (2E,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,9Z,12Z)-octadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 13 morecytosol

• (2E,4Z,7Z,10Z,13Z,16Z,19Z)-docosaheptaenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + O2 = (2E,4Z,7Z,10Z,13Z,16Z,19Z)-docosaheptaenoyl-CoA + H2O2

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• a fatty acyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. an N-acylsphinganine + H2O = sphinganine + a fatty acid
  3. a fatty acid + ATP + CoA = a fatty acyl-CoA + AMP + diphosphate

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

• N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, extracellular spaceOne of 12 routes

• 9-cis-retinolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 9-cis-retinol

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

• an N-acyl-(4R)-4-hydroxysphinganine-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
  3. an N-acyl-(4R)-4-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-(4R)-4-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

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

• an N-acyl-(4R)-4-hydroxysphinganine-1-phosphoethanolamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
  3. an N-acyl-(4R)-4-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acyl-(4R)-4-hydroxysphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

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

• hexadecanoateReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. hexadecanoate + NADH + 2 H(+) = hexadecanal + NAD(+) + H2O

  Catalysed by DBP, SPHK2, SPHK1, SGPL1 and 3 morecytosol, endoplasmic reticulum

• tricosanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (tricosanoic acid)
  3. Tricosanoyl-CoA hydrolase

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

• thio-Mo-molybdopterinReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

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

• cholesteryl octadecanoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol, endoplasmic reticulumOne of 2 routes

• N-octadecanoylhexadecasphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. hexadecasphinganine + octadecanoyl-CoA = N-octadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphate = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• 1,2-dihexadecanoyl-sn-glycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• glycodeoxycholateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. deoxycholoyl-CoA to glycodeoxycholate conversion

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosolOne of 3 routes

• 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerol + a sphingomyelin = a 1-(9Z-octadecenoyl)-2-acyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine

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

• sphinga-4E,14Z-dienineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• O-octadecanoyl-(R)-carnitineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

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

• O-eicosanoyl-(R)-carnitineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Carnitine O-Palmitoyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, peroxisomeOne of 7 routes

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

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

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

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

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

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

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol

• N-tetradecanoylglycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosolOne of 2 routes

• N-eicosanoylglycinateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosolOne of 2 routes

• N-docosanoylglycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosolOne of 2 routes

• N-hexacosanoylglycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosolOne of 2 routes

• an N(2)-acyl-L-glutamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

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

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

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