sphinganine

Three steps

• phosphatidic acidReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. Diacylglycerol Phosphate Kinase (Homo Sapiens)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 morenucleusOne of 2 routes

• octadecanalReach from here →
  1. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)
  2. N-(octadecanoyl)-sphinganine + H2O = sphinganine + octadecanoate
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 more

• linoleic acidReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• a 2-acylglycerolReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. a 1,2-diacyl-sn-glycerol + H2O = a 2-acylglycerol + a fatty acid + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 more

• a monoacylglycerolReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + H2O = sphinganine + a fatty acid
  3. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 moreOne of 9 routes

• all-trans-retinyl hexadecanoateReach from here →
  1. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  2. sphinganine + hexadecanoate = N-hexadecanoylsphinganine + H2O
  3. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)

  Catalysed by CERS6, CERS5, CERS2, ASAH2 and 1 more

• a sphingomyelinReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 morecytosol, Golgi apparatusOne of 8 routes

• a triacylglycerolReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 7 morecytosol

• dodecanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• D-glucosyl-N-acylsphingosineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. UDP-glucose:N-acylsphingosine D-glucosyltransferase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 3 morecytosolOne of 2 routes

• a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 3 morecytosolOne of 2 routes

• a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 morecytosolOne of 2 routes

• a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. an N-acylsphing-4-enine + UDP-alpha-D-glucose = a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 3 morecytosolOne of 2 routes

• S-hexadecanoyl-N-acetylcysteamineReach from here →
  1. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  2. sphinganine + hexadecanoate = N-hexadecanoylsphinganine + H2O
  3. S-hexadecanoyl-N-acetylcysteamine + H2O = N-acetylcysteamine + hexadecanoate + H(+)

  Catalysed by CERS6, CERS5, CERS2, ASAH2 and 2 more

• S-hexadecanoyl-N-acetylcysteine methyl esterReach from here →
  1. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  2. sphinganine + hexadecanoate = N-hexadecanoylsphinganine + H2O
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by CERS6, CERS5, CERS2, ASAH2 and 1 more

• docosanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• alpha-linolenic acidReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• tetradecanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• hexacosanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• tetracosanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• eicosanoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• (9Z)-hexadecenoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• (15Z)-tetracosenoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• (11Z)-eicosenoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• a fatty aldehydeReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + H2O = sphinganine + a fatty acid
  3. a fatty aldehyde + NAD(+) + H2O = a fatty acid + NADH + 2 H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 more

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. sphinganine + (9Z)-octadecenoyl-CoA = N-(9Z-octadecenoyl)-sphinganine + CoA + H(+)
  2. H2O[r] + N-(9Z-octadecenoyl)-sphinganine[r] = oleate[r] + sphinganine[r]
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O

  Catalysed by CERS5, CERS2, ACER3, DGAT1 and 4 moreendoplasmic reticulum

• 16-hydroxyhexadecanoateReach from here →
  1. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  2. sphinganine + hexadecanoate = N-hexadecanoylsphinganine + H2O
  3. hexadecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 16-hydroxyhexadecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CERS6, CERS5, CERS2, ASAH2 and 3 more

• hexadecanoyl-CoAReach from here →
  1. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)
  2. sphinganine + hexadecanoate = N-hexadecanoylsphinganine + H2O
  3. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate

  Catalysed by CERS6, CERS5, CERS2, ASAH2 and 11 more

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

  Catalysed by CERS5, CERS2, ACER3, SLC27A2 and 7 moreendoplasmic reticulum

• octadecanoyl-CoAReach from here →
  1. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)
  2. N-(octadecanoyl)-sphinganine + H2O = sphinganine + octadecanoate
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosolOne of 6 routes

• (R)-2-hydroxyoctadecanoateReach from here →
  1. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)
  2. N-(octadecanoyl)-sphinganine + H2O = sphinganine + octadecanoate
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 more

• ethanolamineReach from here →
  1. sphinganine + ATP = sphinganine 1-phosphate + ADP + H(+)
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. Phosphoethanolamine phosphohydrolase

  Catalysed by SPHK2, SPHK1, SGPL1, PHOSPHO1endoplasmic reticulum, cytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 3 moreOne of 8 routes

• an N-acylsphing-4-enine 1-phosphateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. an N-acylsphing-4-enine + ATP = an N-acylsphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 morecytosol

• sphing-4-enineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 6 morecytosol, Golgi apparatusOne of 4 routes

• CDP-ethanolamineReach from here →
  1. sphinganine + ATP = sphinganine 1-phosphate + ADP + H(+)
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. CTP:ethanolamine-phosphate cytidylyltransferase

  Catalysed by SPHK2, SPHK1, SGPL1, PCYT2endoplasmic reticulum, cytosolOne of 3 routes

• an acyl-CoAReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 6 morecytosol, Golgi apparatusOne of 3 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. a 1,2-diacyl-sn-glycerol + ATP = a 1,2-diacyl-sn-glycero-3-phosphate + ADP + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 13 more

• an all-trans-retinyl esterReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + H2O = sphinganine + a fatty acid
  3. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 more

• (4R)-hydroxysphinganineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
  3. Phytoceramide amidohydrolase

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 7 morecytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. CDP-ethanolamine + a 1,2-diacyl-sn-glycerol = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CMP + H(+)

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 4 more

• a triacyl-sn-glycerolReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 8 more

• N-hexadecanoyl-(4R)-hydroxysphinganineReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
  3. N-hexadecanoyl-(4R)-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-(4R)-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 3 more

• (2E)-octadecenoyl-CoAReach from here →
  1. sphinganine + (9Z)-octadecenoyl-CoA = N-(9Z-octadecenoyl)-sphinganine + CoA + H(+)
  2. H2O[g] + N-(9Z-octadecenoyl)-sphinganine[g] = elaidate[g] + sphinganine[g]
  3. fatty-acid-CoA ligase

  Catalysed by CERS5, CERS2, ACER3, ACSL1Golgi apparatus, cytosol

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. a fatty acyl-CoA + sphinganine = an N-acylsphinganine + CoA + H(+)
  2. N-acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CERS1, CERS6, CERS5, CERS4 and 5 morecytosol, extracellular spaceOne of 12 routes

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

  Catalysed by CERS5, CERS2, ACER3, ABHD12endoplasmic reticulum

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

  Catalysed by CERS5, CERS2, ACER3, ABHD16Aendoplasmic reticulum