CHEBI:16566

Three steps

• L-methionine (S)-S-oxideReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrix

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrixOne of 4 routes

• 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• L-prolineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 3 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sphing-4-enine 1-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol, Golgi apparatus

• N-benzoylglycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, mitochondrial matrixOne of 8 routes

• L-cysteinylglycineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 8 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-hexenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. medium-chain acyl-CoA ligase (hexanoic acid)
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• a cardiolipinReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus

• (2E)-octenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosol, mitochondrial matrixOne of 5 routes

• 3-oxotetradecanoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + malonyl-CoA + H(+) = 3-oxotetradecanoyl-CoA + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• an all-trans-retinyl esterReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol, Golgi apparatusOne of 5 routes

• (4R)-hydroxysphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)
  3. Phytoceramide amidohydrolase

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosolOne of 2 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 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(+)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol, Golgi apparatusOne of 2 routes

• a triacyl-sn-glycerolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, Golgi apparatusOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 9 morecytosol, Golgi apparatus

• 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phospho-D-myo-inositol + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol

• 3-oxoeicosasphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + L-serine + H(+) = 3-oxoeicosasphinganine + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol

• N-hexadecanoyl-(4R)-hydroxysphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  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, CERS3, CERS5 and 5 morecytosol

• 3-oxoeicosanoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 16 morecytosolOne of 2 routes

• N-docosanoylsphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. docosanoyl-CoA + sphinganine = N-docosanoylsphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 4 morecytosolOne of 2 routes

• N-(2-hydroxydocosanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. 2-hydroxydocosanoyl-CoA + sphinganine = N-(2-hydroxydocosanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 3 morecytosol

• N-eicosanoylsphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. eicosanoyl-CoA + sphinganine = N-eicosanoylsphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 4 morecytosolOne of 2 routes

• N-(octadecanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 7 morecytosolOne of 2 routes

• N-(2-hydroxyoctadecanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. 2-hydroxyoctadecanoyl-CoA + sphinganine = N-(2-hydroxyoctadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 3 morecytosol

• N-hexadecanoylsphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 4 morecytosolOne of 2 routes

• N-(2-hydroxyhexadecanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. 2-hydroxyhexadecanoyl-CoA + sphinganine = N-(2-hydroxyhexadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol

• N-(tetradecanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 3 morecytosolOne of 2 routes

• 3-oxohexadecasphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol

• 3-oxotetradecasphinganineReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + L-serine + H(+) = 3-oxotetradecasphinganine + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol

• Mo-molybdopterinReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 3 morecytosol, mitochondrial matrix

• 3-oxooctadecanoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Palmitate:CoA ligase (AMP-forming)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 17 morecytosolOne of 2 routes

• 3-oxodocosanoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. very-long-chain 3-oxoacyl-CoA synthase (eicosanoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 17 morecytosolOne of 3 routes

• 3-oxo-(8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z)-eicosatrienoyl-CoA + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol

• 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearidonic acid)
  3. (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoA + CO2 + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 5 morecytosol, endoplasmic reticulumOne of 14 routes

• N-(octacosanoyl)-sphinganineReach from here →
  1. ATP:sphinganine 1-phosphotransferase
  2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
  3. octacosanoyl-CoA + sphinganine = N-(octacosanoyl)-sphinganine + CoA + H(+)

  Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol

• 1-dodecanoyl-sn-glycerol 3-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. glycerol-3-phosphate 1-O-acyltransferase (lauroyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosolOne of 2 routes

• 1-tetradecanoyl-sn-glycerol 3-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z,12Z)-octadecadienoyl-CoA = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z,12Z)-octadecadienoyl-CoA = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. sphingosine N-acyltransferase (sphinganine)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol