N-hexadecanoylsphing-4-enine

Three steps

• 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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. a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-O-acyl-N-(acetyl)-sphing-4-enine

  Catalysed by NAAA, PAFAH2, PLA2G15nucleus, cytosol

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bnucleus, cytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 5 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by NAAA, CRAT, CROTnucleus, cytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by NAAA, ACAA1, HSD17B4, EHHADH and 1 morenucleus, cytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Production of Hexadecanedioylcarnitine

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bnucleus, cytosolOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bnucleus, cytosol, endoplasmic reticulumOne of 7 routes

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by NAAA, ABHD11nucleus, cytosol

• (11Z,14Z)-eicosadienoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• (17Z)-hexacosenoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• pristanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. fatty-acid-CoA ligase

  Catalysed by NAAA, SLC27A2nucleus, cytosolOne of 2 routes

• 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 12 moreOne of 2 routes

• 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 12 more

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine

  Catalysed by NAAA, PAFAH2, PLA2G15nucleus, cytosol

• 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 12 more

• undecanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by NAAA, ACSM4, ACSM1, ACSM2A and 3 morenucleus, cytosolOne of 3 routes

• 1-O-hexadecyl-sn-glycero-3-phosphateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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-glycero-3-phosphate + choline + H(+)

  Catalysed by NAAA, PAFAH2, ENPP2, GDPD3 and 1 morenucleus, cytosol

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• tricosanoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAnucleus, cytosol, extracellular spaceOne of 12 routes

• 7alpha-hydroxypregnenoloneReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. pregnenolone,NADPH:oxygen oxidoreductase (7alpha-hydroxylating)

  Catalysed by GBA1, CYP11A1, CYP7B1cytosolOne of 2 routes

• N-hexadecanoylhexadecasphinganineReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. hexadecasphinganine + hexadecanoyl-CoA = N-hexadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 13 more

• (24S)-24-hydroxycholesterol esterReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol = (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by GBA1, CYP46A1, LCAT

• (24S)-hydroxycholesterol 3-linoleoateReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine = (24S)-hydroxycholesterol 3-linoleoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by GBA1, CYP46A1, LCAT

• 1,2-dihexadecanoyl-sn-glycerolReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 4 morenucleus, cytosol

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by GBA1, LCAT, LPCAT1

• 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerolReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  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 NAAA, CERS1, CERS6, CERS3 and 5 morenucleus, cytosol

• 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + hexadecanoyl-CoA = 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 12 more

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phosphoserine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by NAAA, PAFAH2, PLA2G15nucleus, cytosol

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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. 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

  Catalysed by NAAA, PAFAH2, PLA2G15nucleus, cytosolOne of 8 routes

• (5Z)-tetradecenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by NAAA, CRAT, CROTnucleus, cytosol, endoplasmic reticulum, peroxisomeOne of 5 routes

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by NAAA, CERS1, TLCD3B, CERS2 and 2 morenucleus, cytosolOne of 2 routes

• (3E)-decenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by NAAA, ACADM, ECHS1, ACAA2 and 1 morenucleus, cytosol, mitochondrial matrix

• N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  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. N-(acetyl)-sphing-4-enine + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by NAAA, PAFAH2, CERKnucleus, cytosol

• 24S,25-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 24S,25-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, CYP46A1

• (24S,25R)-24,26-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, CYP46A1

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by NAAA, HADHA, ACAA2, HADHBnucleus, cytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. stearoyl-CoA 9-desaturase (palmitoyl-CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 7 morenucleus, cytosolOne of 9 routes

• tricosanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 4 routes