N-hexadecanoylsphing-4-enine

Three steps

• propionyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Utilized Transport
  3. Active Transport

  Catalysed by NAAAnucleus, cytosol, endoplasmic reticulum, mitochondrial matrixOne of 45 routes

• a 1-hexadecanoyl-2-acylglycerolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 2-acylglycerol + hexadecanoyl-CoA = a 1-hexadecanoyl-2-acylglycerol + CoA

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

• an hexadecanoyl-acylglycerolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 1-acylglycerol + hexadecanoyl-CoA = an hexadecanoyl-acylglycerol + CoA

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

• 1-(10Z-heptadecenoyl)-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. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-(10Z-heptadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

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

• CHEBI:15650Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by NAAA, ZDHHC11B, NAA10, ESCO2 and 29 morenucleus, cytosolOne of 2 routes

• betaine aldehydeReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by GBA1, CH25H, CHDH

• CHEBI:15727Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by NAAA, NAA10nucleus, cytosol

• CHEBI:15746Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by NAAA, SAT1, SAT2nucleus, cytosolOne of 2 routes

• hexadecan-1-olReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. formate dehydrogenase (palmitoyl-CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 7 morenucleus, cytosol, peroxisomeOne of 2 routes

• sulfateReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)
  3. Cholesterol-sulfate sulfohydrolase

  Catalysed by GBA1, SULT2B1, SULT1C2, STScytosolOne of 4 routes

• 11-cis-retinyl hexadecanoateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 10 morenucleus, cytosolOne of 2 routes

• 11-cis-retinolReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by NAAA, DGAT1, LRAT, AWAT1 and 2 morenucleus, cytosolOne of 2 routes

• oxaloacetateReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. ATP citrate lyase (citrate)

  Catalysed by NAAA, ACLYnucleus, cytosolOne of 2 routes

• alpha,alpha-trehaloseReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + H2O = N-hexadecanoylsphing-4-enine + beta-D-glucose
  3. alpha,alpha-trehalose + H2O = alpha-D-glucose + beta-D-glucose

  Catalysed by GBA1, LCT, TREH

• 1-phosphatidyl-1D-myo-inositolReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)
  3. ATP:1-Phosphatidyl-1D-myo-inositol 4-phosphotransferase

  Catalysed by GBA1, OSBP, PTPRQ, INPPL1 and 11 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• formaldehydeReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + 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 GBA1, CH25H, KDM1A, KDM1BOne of 3 routes

• sn-glycerol 3-phosphocholineReach 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 + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-O-hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + sn-glycerol 3-phosphocholine

  Catalysed by NAAA, PAFAH2, PLA2G4Cnucleus, cytosolOne of 7 routes

• progesteroneReach 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:NAD+ 3-oxidoreductase

  Catalysed by GBA1, CYP11A1, HSD3B1, HSD3B2cytosolOne of 2 routes

• octadecanalReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by NAAA, ALDH3A2nucleus, cytosol

• anilineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by NAAA, NAT2, NAT1nucleus, cytosol

• CHEBI:17312Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by NAAAnucleus, cytosolOne of 2 routes

• all-trans-retinolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)
  3. all-trans-retinyl hexadecanoate + H2O = all-trans-retinol + hexadecanoate + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 4 moreOne of 2 routes

• linoleic acidReach 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 16 routes

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 7 morenucleus, cytosol, peroxisomeOne of 15 routes

• AH2Reach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by GBA1, CH25H, AIFM1, PYROXD1One of 19 routes

• O-phosphoethanolamineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. ATP:sphingosine 1-phosphotransferase
  3. sphingosine-1-phosphate palmitaldehyde-lyase (phosphoethanolamine-forming)

  Catalysed by NAAA, DBP, SPHK2, SPHK1 and 1 morenucleus, cytosolOne of 2 routes

• L-cysteineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by NAAA, NAGSnucleus, cytosol, mitochondrial matrixOne of 2 routes

• (2E)-hexadecenalReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. ATP:sphingosine 1-phosphotransferase
  3. sphingosine-1-phosphate palmitaldehyde-lyase (phosphoethanolamine-forming)

  Catalysed by NAAA, DBP, SPHK2, SPHK1 and 1 morenucleus, cytosolOne of 2 routes

• a sphingomyelinReach 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. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 5 morenucleus, cytosol, Golgi apparatusOne of 8 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

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

• a 1,2-diacyl-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. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 5 morenucleus, cytosol, Golgi apparatusOne of 9 routes

• 7alpha-hydroxycholest-4-en-3-oneReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. Cholest-5-Ene-3Beta, 7Alpha-Diol:NAD+ 3-Oxidoreductase Bile Acid Biosynthesis

  Catalysed by GBA1, CH25H, HSD3B7endoplasmic reticulumOne of 5 routes

• alpha-D-glucoseReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + H2O = N-hexadecanoylsphing-4-enine + beta-D-glucose
  3. alpha-D-glucose = beta-D-glucose

  Catalysed by GBA1, LCT, GALM

• CHEBI:17927Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by NAAAnucleus, cytosol

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

  Catalysed by NAAA, SLC25A20nucleus, cytosol, endoplasmic reticulum, mitochondrial matrixOne of 7 routes

• dodecanoateReach 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 14 routes

• D-glucosyl-N-acylsphingosineReach 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. UDP-glucose:N-acylsphingosine D-glucosyltransferase

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 4 morenucleus, cytosolOne of 2 routes

• a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach 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. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 4 morenucleus, cytosolOne of 3 routes

• a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enineReach 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. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 5 morenucleus, cytosolOne of 3 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-sphing-4-enine + UDP-alpha-D-xylose = beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enine + UDP + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ACER1 and 3 morenucleus, cytosol

• 1D-myo-inositol 1,4,5-trisphosphateReach from here →
  1. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(in) + cholesterol(out)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) + H2O = 1D-myo-inositol 1,4,5-trisphosphate + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by GBA1, OSBP2, OSBPL2, PLCH2 and 12 moreinner side of the membrane, outer side of the membrane

• a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enineReach 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. an N-acylsphing-4-enine + UDP-alpha-D-glucose = a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 4 morenucleus, cytosolOne of 3 routes

• (5Z)-dodecenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by NAAA, HADHA, ACAA2, HADHBnucleus, cytosol, mitochondrial matrixOne of 2 routes

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

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

• (7Z)-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 ((7Z)-tetradecenoic acid)

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

• a 2-hexadecanoyl-6-alpha-D-glucosaminy-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 6-(alpha-D-glucosaminyl)-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositol + hexadecanoyl-CoA = a 2-hexadecanoyl-6-alpha-D-glucosaminy-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositol + CoA

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

• N-acetylcysteine methyl esterReach from here →
  1. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  2. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 1 more

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by NAAA, HADHA, ACADVL, HADHBnucleus, cytosol, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by NAAA, ECHS1, ACAA2, HADHnucleus, cytosol, mitochondrial matrixOne of 2 routes