N-(acetyl)-sphing-4-enine

Three steps

• 1-heptanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-diheptanoyl-sn-glycero-3-phosphocholine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-heptanoyl-sn-glycero-3-phosphocholine + 1-heptanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by PLA2G15, PRDX6, LPCAT3, LPCAT1 and 1 more

• 1,2-diheptadecanoyl-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamineReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-diheptadecanoyl-sn-glycero-3-phosphoethanolamine + 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine = 1,2-diheptadecanoyl-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H(+)

  Catalysed by PLA2G15, LPCAT3, LPCAT1, PLAAT3 and 2 more

• 1,2-diheptadecanoyl-sn-glycero-3-phospho-N-(9Z-octadecenoyl)-ethanolamineReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-diheptadecanoyl-sn-glycero-3-phosphoethanolamine + 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine = 1,2-diheptadecanoyl-sn-glycero-3-phospho-N-(9Z-octadecenoyl)-ethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by PLA2G15, LPCAT3, LPCAT1, PLAAT3 and 2 more

• 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamineReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by PLA2G15, PRDX6, LPCAT3, LPCAT1 and 1 more

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + choline + H(+)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by PLA2G15, ENPP2, GDPD1, AGPAT4

• beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 more

• 3-(9Z-octadecenoyl)-sn-glycero-1-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = 1-(9Z-octadecenoyl)-sn-glycerol + phosphocholine + H(+)
  3. 3-lyso-sn-glycero-1-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + 1-(9Z-octadecenoyl)-sn-glycerol = 3-(9Z-octadecenoyl)-sn-glycero-1-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + glycerol

  Catalysed by PLA2G15, ENPP6, ABHD12, PLD3 and 1 more

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A7 and 3 moreextracellular space, cytosol, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A7 and 25 moreextracellular space, cytosolOne of 2 routes

• an N-acyl-sphinga-4E,14Z-dienineReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = an N-acyl-sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by ASAH1, CERS1, CERS6, CERS3 and 4 more

• a 2-acyl-6-[alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + a 1-acyl-sn-glycero-3-phosphocholine = sn-glycerol 3-phosphocholine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  3. a 2-acyl-6-[alpha-D-mannosyl-(1->6)-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = a 2-acyl-6-[alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycerol

  Catalysed by PLA2G15, ASPG, PIGN

• a 2-acyl-6-[2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + a 1-acyl-sn-glycero-3-phosphocholine = sn-glycerol 3-phosphocholine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  3. a 2-acyl-6-(alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl)-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = a 2-acyl-6-[2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycerol

  Catalysed by PLA2G15, ASPG, PIGN

• a 2-acyl-6-[6-phosphoethanolamine-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + a 1-acyl-sn-glycero-3-phosphocholine = sn-glycerol 3-phosphocholine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  3. a 2-acyl-6-[alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = a 2-acyl-6-[6-phosphoethanolamine-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycerol

  Catalysed by PLA2G15, ASPG, PIGO

• a 2-acyl-6-[6-phosphoethanolamine-alpha-D-mannosyl-(1->2)-6-phosphoethanolamine-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + a 1-acyl-sn-glycero-3-phosphocholine = sn-glycerol 3-phosphocholine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  3. a 2-acyl-6-[6-phosphoethanolamine-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = a 2-acyl-6-[6-phosphoethanolamine-alpha-D-mannosyl-(1->2)-6-phosphoethanolamine-alpha-D-mannosyl-(1->6)-2-phosphoethanolamine-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-(1-radyl,2-acyl-sn-glycero-3-phospho)-1D-myo-inositol + a 1,2-diacyl-sn-glycerol

  Catalysed by PLA2G15, ASPG, PIGG

• 1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + O2 = 1-octadecanoyl-2-(15-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-phosphocholine

  Catalysed by PLA2G15, LPGAT1, ALOX15B

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by PLA2G15, PLA2G6, ASPGcytosolOne of 2 routes

• 1-O-(1Z-alkenyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine = 1-O-(1Z-alkenyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by PLA2G15, LPCAT3, MBOAT2, LPCAT1 and 1 more

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

  Catalysed by ASAH1, FADS3, CERS6, CERS5

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by PLA2G15, PLA2G6, ASPG, FAAH and 1 more

• acetaldehydeReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine
  2. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + ethanolamine + H(+)
  3. ethanolamine ammonia-lyase (acetaldehyde-forming)

  Catalysed by PLA2G15, GDPD1cytosolOne of 4 routes

• CHEBI:15345Reach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A6 and 3 moreextracellular space, cytosolOne of 3 routes

• acetoneReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. Acetoacetate carboxy-lyase (acetone-forming)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A6 and 2 moreextracellular space, cytosol, mitochondrial matrix

• acetylcholineReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + choline + H(+)
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by PLA2G15, ENPP2, GDPD1, CHATcytosolOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by PLA2G15, PLA2G6, ASPG, SLC27A2 and 7 morecytosolOne of 3 routes

• oleoyl-CoAReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (9Z)-octadecenoate + H(+)
  3. long-chain-fatty-acid-CoA ligase (oleate)

  Catalysed by PLA2G15, PNPLA7, ASPG, PNPLA6 and 8 morecytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and propanoate (cytosol to extracellular)
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A7 and 4 moreextracellular space, cytosolOne of 3 routes

• (S)-malateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosolOne of 2 routes

• 12(S)-HPETEReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by PLA2G15, PLA2G6, ASPG, ALOX12cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by PLA2G15, PLA2G6, ASPG, ALOX15B and 1 morecytosolOne of 4 routes

• 5(S)-HPETEReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by PLA2G15, PLA2G6, ASPG, ALOX5cytosol

• 10-formyltetrahydrofolic acidReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and formate (cytosol to extracellular)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A1 and 1 moreextracellular space, cytosolOne of 2 routes

• betaine aldehydeReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + choline + H(+)
  3. choline dehydrogenase (choline)

  Catalysed by PLA2G15, ENPP2, GDPD1, CHDHcytosolOne of 4 routes

• hexadecanoic acidReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. ATP:sphingosine 1-phosphotransferase
  3. sphingosine-1-phosphate lyase (sphingosine-1-phosphate)

  Catalysed by ASAH1, DBP, SPHK2, SPHK1 and 1 morecytosol, endoplasmic reticulumOne of 2 routes

• a 1-O-alkyl-sn-glycerolReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. a 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine + a 1-O-alkyl-sn-glycero-3-phosphocholine
  3. a 1-O-alkyl-sn-glycero-3-phosphocholine + H2O = a 1-O-alkyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by PLA2G15, LCAT, ENPP6

• alpha-D-glucosamine 6-phosphateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
  3. N-Acetyl-D-glucosamine-6-phosphate amidohydrolase

  Catalysed by ASAH1, AMDHD2, CEMP1cytosol

• CHEBI:15978Reach from here →
  1. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (9Z)-octadecenoate + H(+)
  3. sn-Glycero-3-phosphocholine glycerophosphohydrolase

  Catalysed by PLA2G15, PNPLA7, ASPG, PNPLA6 and 1 morecytosol

• cholesterolReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by ASAH1, CERS1, CERS6, CERS3 and 5 moreOne of 9 routes

• 2-methyl-3-oxopropanoic acidReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosol, mitochondrial matrix

• (17R,20S)-17,20-dihydroxypregn-4-en-3-oneReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD(+) = 17alpha-hydroxyprogesterone + NADH + H(+)

  Catalysed by ASAH1, CYP17A1, AKR1C1endoplasmic reticulumOne of 2 routes

• androst-4-ene-3,17-dioneReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by ASAH1, CYP17A1endoplasmic reticulum, cytosolOne of 5 routes

• oxaloacetateReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O
  3. (R)-malate + A = oxaloacetate + AH2

  Catalysed by PLA2G15, PTGS2, D2HGDHOne of 4 routes

• (S)-lactateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 7 moreextracellular space, cytosol

• 2-oxobutanoateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of 2-hydroxybutyrate and acetate (cytosol to extracellular)
  3. 2-hydroxybutyrate:NAD+ oxidoreductase

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A7 and 5 moreextracellular space, cytosolOne of 2 routes

• 2-oxoglutaramateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. L-Glutamine:pyruvate aminotransferase

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosolOne of 2 routes

• formaldehydeReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O
  3. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by PLA2G15, PTGS2, KDM1A, KDM1BOne of 3 routes

• 3-fumarylpyruvateReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. 3-fumarylpyruvate + H2O = fumarate + pyruvate + H(+)

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosol

• CHEBI:16856Reach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by PLA2G15, PLA2G6, ASPGextracellular space, cytosolOne of 2 routes

• ferrocytochrome cReach from here →
  1. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  2. transport of acetate and L-lactate (cytosol to extracellular)
  3. (S)-Lactate:ferricytochrome-c 2-oxidoreductase

  Catalysed by ASAH1, SLC16A4, SLC16A5, SLC16A3 and 4 moreextracellular space, cytosol, mitochondrial matrix

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + choline + H(+)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by PLA2G15, ENPP2, GDPD3, GDPD1cytosolOne of 16 routes

• octadecanalReach from here →
  1. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-octadecanoyl-sn-glycero-3-phosphocholine
  2. 1-octadecanoyl-sn-glycero-3-phosphocholine + H2O = octadecanoate + sn-glycerol 3-phosphocholine + H(+)
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by PLA2G15, LYPLA2, ASPG, ALDH3A2