N-hexadecanoylsphing-4-enine

Three steps

• (5Z)-octenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

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

• docosanoateReach 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

• octanoateReach 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-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. N-octanoylsphing-4-enine + H2O = octanoate + sphing-4-enine

  Catalysed by GBA1, ASAH1, ASAH2

• alpha-linolenic 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 13 routes

• CHEBI:27540Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by NAAA, ACSM4, ACSM1, ACSM2A and 3 morenucleus, cytosolOne of 6 routes

• elaidic 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 18 routes

• alpha-D-galactoseReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase
  3. galactosylceramidase (psychosine)

  Catalysed by NAAA, GALCnucleus, cytosol, lysosome

• all-cis-docosa-4,7,10,13,16,19-hexaenoic 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 12 routes

• 1-(9Z-octadecenoyl)-sn-glycero-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. 1,2-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

  Catalysed by NAAA, PAFAH2, PLA2G15nucleus, cytosolOne of 4 routes

• CHEBI:28701Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by NAAA, ACAA1, SCP2, MYO5Bnucleus, cytosol, peroxisomeOne of 7 routes

• 17alpha-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. cytochrome P450 (pregnenolone)

  Catalysed by GBA1, CYP11A1, CYP17A1cytosolOne of 3 routes

• a fatty acidReach 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 + H2O = sphing-4-enine + a fatty acid

  Catalysed by NAAA, CERS1, CERS6, CERS3 and 8 morenucleus, cytosolOne of 2 routes

• chlorine(.)Reach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Utilized Transport
  3. Carnitine Transport by Atb0

  Catalysed by NAAA, SLC6A14nucleus, cytosol, endoplasmic reticulum, extracellular space

• 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 + H2O = 1-O-hexadecyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by NAAA, PAFAH2, SMPD2nucleus, cytosolOne of 2 routes

• acetateReach 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 + H2O = sphing-4-enine + acetate

  Catalysed by NAAA, PAFAH2, ASAH1nucleus, cytosol

• tetradecanoateReach 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 13 routes

• (9Z)-octadecenoateReach 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 19 routes

• a 1-O-alkyl-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. 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

  Catalysed by GBA1, LCAT

• hexacosanoateReach 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

• tetracosanoateReach 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 13 routes

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

  Catalysed by NAAA, ASAH1, ACER2, ACER1 and 2 morenucleus, cytosol

• eicosanoateReach 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 13 routes

• (9Z)-hexadecenoateReach 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 18 routes

• (15Z)-tetracosenoateReach 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 13 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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 15 routes

• (11Z)-eicosenoateReach 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

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-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 + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by NAAA, PAFAH2, LPCAT4nucleus, cytosol

• 1-O-hexadecyl-sn-glycerolReach 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-glycerol + phosphocholine + H(+)

  Catalysed by NAAA, PAFAH2, SMPD2nucleus, cytosol

• 7alpha,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 + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. cytochrome P450 (25-hydroxycholesterol)

  Catalysed by GBA1, CH25H, CYP7B1endoplasmic reticulumOne of 2 routes

• (24S)-7alpha-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 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 7alpha-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-7alpha-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, CYP7A1, CYP46A1One of 4 routes

• 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. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesteryl 3-beta-D-glucoside + H2O = cholesterol + D-glucose

  Catalysed by GBA1, GBA2One of 2 routes

• 1-O-hexadecyl-2-acetyl-sn-glycero-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 + acetyl-CoA = 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by NAAA, PAFAH2, LPCAT2, LPCAT1nucleus, cytosol

• taurineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by NAAA, BAATnucleus, cytosolOne of 2 routes

• 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-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 + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by NAAA, PAFAH2, LPCAT4nucleus, cytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(out)

  Catalysed by GBA1, OSBP, OSBPL9, OSBPL11 and 4 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• glycineReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by NAAA, GLYAT, GLYATL2, GLYATL1nucleus, cytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by NAAA, ALDH6A1nucleus, cytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by NAAAnucleus, cytosol, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by NAAA, ACP2nucleus, cytosol, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by NAAAnucleus, cytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by NAAA, ACAA1, MYO5Bnucleus, cytosol, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 7 routes

• butanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by NAAA, SLC33A1, ESCO2, OXSMnucleus, cytosol, endoplasmic reticulum, mitochondrial matrixOne of 11 routes

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

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 9 routes

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

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

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

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 12 routes

• itaconyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by NAAA, SUCLG1, SUCLG2, SUCLA2nucleus, cytosol, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morenucleus, cytosolOne of 13 routes

• tetradecanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 8 morenucleus, cytosol, mitochondrial matrixOne of 13 routes

• octanoyl-CoAReach from here →
  1. H2O[c] + N-hexadecanoylsphing-4-enine[c] = palmitate[c] + sphingosine[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. Beta Oxidation of Long Chain Fatty Acid

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 7 morenucleus, cytosol, mitochondrial matrixOne of 22 routes