N-(9Z-octadecenoyl)-sphinganine

Three steps

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 6 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 2 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) = 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by ACER3, ABHD12, CLN5endoplasmic reticulum

• (7Z)-tetradecenoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 9 routes

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-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 (C18:4->C16:4), Mitochondrial

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

• (7Z,10Z)-hexadecadienoyl-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 Trans (C18:2->C16:2), Mitochondrial

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

• (4Z,7Z)-decadienoyl-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 (C12:3->C10:2), Mitochondrial

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

• (5Z)-octenoyl-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 (C10:2->C8:1), Mitochondrial

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

• docosanoateReach 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

• octadecanoateReach 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 13 routes

• alpha-linolenic 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 13 routes

• CHEBI:27540Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 9 moreendoplasmic reticulum, cytosolOne of 6 routes

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

• CHEBI:28701Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, peroxisomeOne of 7 routes

• a fatty acidReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

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

• chlorine(.)Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. Utilized Transport
  3. Carnitine Transport by Atb0

  Catalysed by ACER3, SLC6A14endoplasmic reticulum, cytosol, extracellular space

• tetradecanoateReach 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

• hexacosanoateReach 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

• tetracosanoateReach 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

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

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

• eicosanoateReach 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

• (9Z)-hexadecenoateReach 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 18 routes

• (15Z)-tetracosenoateReach 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

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

• (11Z)-eicosenoateReach 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

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

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

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach 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-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by ACER3, SLC27A2, ACSL4, ACSL3 and 7 moreendoplasmic reticulum, cytosolOne of 2 routes

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

  Catalysed by ACER3, MOGAT2, MOGAT1Golgi apparatus, cytosol

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

  Catalysed by ACER3, MOGAT2, MOGAT3, LPGAT1 and 2 moreGolgi apparatus, cytosolOne of 2 routes

• taurineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosolOne of 2 routes

• 1,2-di-(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-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 11 moreendoplasmic reticulumOne of 3 routes

• 1,2-di-(9Z-octadecenoyl)-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. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by ACER3, SLC27A2, ACSL3, ACSL1 and 8 moreendoplasmic reticulumOne of 2 routes

• an N-acylsphing-4-enineReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. delta 4-desaturase, sphingolipid (dihydroceramide pool)

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

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by ACER3, LPCAT4, LPCAT3, MBOAT1Golgi apparatus, cytosol

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

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. (S)-methylmalonyl-CoA hydrolase

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

• 3'-dephospho-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 4 moreendoplasmic reticulum, cytosol, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. (2E)-dodecenoyl-CoA formation

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

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 8 routes

• butanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by ACER3, SLC33A1, ESCO2, OXSMendoplasmic reticulum, cytosol, mitochondrial matrixOne of 11 routes

• dodecanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 10 routes

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

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

• eicosanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 11 moreendoplasmic reticulum, cytosolOne of 13 routes

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

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

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)

  Catalysed by ACER3, SLC27A2, ACSL4, ACSL3 and 6 moreendoplasmic reticulum, cytosolOne of 17 routes

• tetradecanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. sphingosine N-acyltransferase (sphinganine)
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

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

• octanoyl-CoAReach from here →
  1. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Beta Oxidation Fatty Acid

  Catalysed by ACER3, SLC27A2, ACSL4, ACSL3 and 7 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 21 routes

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

  Catalysed by ACER3, CERS1, CERS6, CERS3 and 3 moreendoplasmic reticulum, cytosolOne of 5 routes