N-(9Z-octadecenoyl)-sphinganine

Three steps

• 2-methylcrotonoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Production of Tiglylcarnitine

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 5 moreendoplasmic reticulum, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 12 routes

• CHEBI:15519Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. propanoyl-CoA C-acyltransferase

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 12 routes

• phenylacetyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Phenylacetate:CoA ligase

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 3 moreendoplasmic reticulum, cytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. Utilized Transport
  3. Active Transport

  Catalysed by ACER3endoplasmic reticulum, cytosol, mitochondrial matrixOne of 45 routes

• L-leucineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by ACER3, PM20D1endoplasmic reticulum

• 1-(10Z-heptadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• CHEBI:15650Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 35 moreendoplasmic reticulum, cytosolOne of 2 routes

• S-(9Z-octadecenoyl)-4'-phosphopantetheineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. (9Z)-octadecenoyl-CoA + H2O = S-(9Z-octadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• CHEBI:15727Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol

• CHEBI:15746Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 5 moreendoplasmic reticulum, cytosolOne of 2 routes

• hexadecanoic acidReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ACER3endoplasmic reticulum, cytosol, extracellular spaceOne of 14 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

  Catalysed by ACER3, GNPATGolgi apparatus, cytosol

• phosphatidylethanolamineReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by ACER3, LPCAT4, LPCAT3, LPCAT2 and 2 moreGolgi apparatus, cytosol

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by ACER3, LPCAT4, LPCAT3, LPCAT2 and 1 moreGolgi apparatus, cytosol

• cholesterolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  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 ACER3, ASAH1, ACER2, ACER1 and 3 moreendoplasmic reticulum

• 11-cis-retinolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 8 moreendoplasmic reticulum, cytosol

• phosphatidic acidReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by ACER3, AGPAT2, LCLAT1, MBOAT1 and 6 moreGolgi apparatus, cytosol, mitochondrial matrixOne of 7 routes

• oxaloacetateReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. ATP citrate lyase (citrate)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

  Catalysed by ACER3, GPAT3, GPAT2, GPAT4 and 1 moreGolgi apparatus, cytosol, mitochondrial matrix

• a cholesterol esterReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + cholesterol = a cholesterol ester + CoA

  Catalysed by ACER3, SOAT2, SOAT1Golgi apparatus, cytosol

• anilineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 5 moreendoplasmic reticulum, cytosol

• CHEBI:17312Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 3 moreendoplasmic reticulum, cytosolOne of 2 routes

• linoleic acidReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ACER3endoplasmic reticulum, cytosol, extracellular spaceOne of 14 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by ACER3, LPCAT4, LPCAT3, LPCAT2 and 1 moreGolgi apparatus, cytosol

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. Utilized Transport
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by ACER3, CPT2, CPT1Aendoplasmic reticulum, cytosol, peroxisomeOne of 10 routes

• O-phosphoethanolamineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. ATP:sphinganine 1-phosphotransferase
  3. Sphinganine-1-phosphate pamlmitaldehyde-lyase

  Catalysed by ACER3, DBP, SPHK2, SPHK1 and 1 moreendoplasmic reticulum, cytosol

• L-cysteineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• hexadecanalReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. ATP:sphinganine 1-phosphotransferase
  3. Sphinganine-1-phosphate pamlmitaldehyde-lyase

  Catalysed by ACER3, DBP, SPHK2, SPHK1 and 1 moreendoplasmic reticulum, cytosolOne of 2 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• a 1,2-diacyl-sn-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 5 moreendoplasmic reticulum, cytosolOne of 5 routes

• a triacylglycerolReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by ACER3, DGAT1, MOGAT2, MOGAT3 and 2 moreGolgi apparatus, cytosol

• CHEBI:17927Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 3 moreendoplasmic reticulum, cytosol

• O-octanoyl-(R)-carnitineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. Utilized Transport
  3. solute carrier (L-carnitine)

  Catalysed by ACER3, SLC25A20endoplasmic reticulum, cytosol, mitochondrial matrixOne of 7 routes

• dodecanoateReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ACER3endoplasmic reticulum, cytosol, extracellular spaceOne of 12 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  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 ACER3, ASAH1, ACER2, ACER1 and 2 moreendoplasmic reticulum

• 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 3-octadecanoyl-sn-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• 1-octanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-dodecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 7 moreendoplasmic reticulum

• 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 7 moreendoplasmic reticulum

• 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 7 moreendoplasmic reticulum

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-tetradecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-(9Z-octadecenyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 11 moreendoplasmic reticulum

• 1-decanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 6 moreendoplasmic reticulum

• (5Z)-dodecenoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes