hexadecanoate

Three steps

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + H2O = 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + hexadecanoate + H(+)

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

• a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + a 2-acyl-sn-glycero-3-phosphocholine = a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + 2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 more

• 1-O-hexadecylglycerone 3-phosphateReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. hexadecanoyl-CoA + 2 NADPH + 2 H(+) = hexadecan-1-ol + 2 NADP(+) + CoA
  3. 1-hexadecanoylglycerone 3-phosphate + hexadecan-1-ol = 1-O-hexadecylglycerone 3-phosphate + hexadecanoate + H(+)

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

• (2E,9Z)-hexadecadienoyl-CoAReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. medium-chain acyl-CoA dehydrogenase (palmitoleoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 moremitochondrial matrixOne of 3 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H2O = 2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + hexadecanoate + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 more

• 1,3-dihexadecanoylglycerolReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + hexadecanoyl-CoA = 1,3-dihexadecanoyl-2-(9Z-octadecenoyl)glycerol + CoA
  3. 1,3-dihexadecanoyl-2-(9Z-octadecenoyl)glycerol + H2O = 1,3-dihexadecanoylglycerol + (9Z)-octadecenoate + H(+)

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

• N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 morenucleus, cytosolOne of 3 routes

• N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = hexadecanoyl-sn-glycero-3-phosphocholine + N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 moreOne of 3 routes

• 9-cis-retinolReach from here →
  1. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)
  2. all-trans-retinyl hexadecanoate + H2O = all-trans-retinol + hexadecanoate + H(+)
  3. retinol binding protein (retinol)

  Catalysed by RPE65, PNLIP, PNPLA4, LIPE and 2 morecytosolOne of 3 routes

• N-hexadecanoyl-sphinganine-1-phosphocholineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  3. N-hexadecanoylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-sphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 more

• N-hexadecanoyl-(4R)-hydroxysphinganine-phosphocholineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. (4R)-hydroxysphinganine + hexadecanoyl-CoA = N-hexadecanoyl-(4R)-hydroxysphinganine + CoA + H(+)
  3. N-hexadecanoyl-(4R)-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-(4R)-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 more

• N-hexadecanoyl-sphinganine-1-phosphoethanolamineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  3. N-hexadecanoylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = N-hexadecanoyl-sphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 more

• N-hexadecanoyl-(4R)-hydroxysphinganine-1-phosphoethanolamineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. (4R)-hydroxysphinganine + hexadecanoyl-CoA = N-hexadecanoyl-(4R)-hydroxysphinganine + CoA + H(+)
  3. N-hexadecanoyl-(4R)-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = N-hexadecanoyl-(4R)-hydroxysphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 more

• cholesteryl octadecanoateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. octadecanoyl-CoA + cholesterol = cholesteryl octadecanoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 moreOne of 2 routes

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. sn-glycerol 3-phosphate + hexadecanoyl-CoA = 1-hexadecanoyl-sn-glycero-3-phosphate + CoA
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 11 more

• 1,2-dihexadecanoyl-sn-glycerolReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphate + CoA
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphate + H2O = 1,2-dihexadecanoyl-sn-glycerol + phosphate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 moreOne of 3 routes

• sphinga-4E,14Z-dienineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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 NAAA, ASAH1, ACER2, ASAH2 and 1 morenucleus, cytosol

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

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

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreOne of 2 routes

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. 1-hexadecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (8Z,11Z,14Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreOne of 2 routes

• N,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

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

• N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  2. 1-octadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 more

• 4beta-hydroxycholesterolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 4beta-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• cholesteryl (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• (6Z,9Z,12Z-octadecatrienoyl)-cholesterolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. 1-hexadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = (6Z,9Z,12Z-octadecatrienoyl)-cholesterol + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• cholesteryl (11Z)-octadecenoateReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more