CHEBI:16566

362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API

602 compounds within 3 steps: 3 in 1, 120 in 2, 479 in 3

Three steps

1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (myristic acid)
3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
N-dodecanoylsphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. acyl-CoA:sphingosine N-acyltransferase
3. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatus
N-tetradecanoylsphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. acyl-CoA:sphingosine N-acyltransferase
3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, Golgi apparatus
N-hexadecanoylsphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. acyl-CoA:sphingosine N-acyltransferase
3. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol, Golgi apparatusOne of 2 routes
N-octadecanoylsphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (stearate)
3. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosolOne of 3 routes
N-eicosanoyl-sphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (eicosanoate)
3. eicosanoyl-CoA + sphing-4-enine = N-eicosanoyl-sphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosolOne of 2 routes
N-tetracosanoyl-sphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (lignocerate)
3. tetracosanoyl-CoA + sphing-4-enine = N-tetracosanoyl-sphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosolOne of 2 routes
1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (stearate)
3. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol
1-hexadecanoyl-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 + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 13 morecytosol
an N-acylsphing-4-enine 1-phosphoethanolamineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. delta 4-desaturase, sphingolipid (dihydroceramide pool)
3. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphing-4-enine 1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol
Catalysed by CERS1, CERS6, CERS3, CERS5 and 7 morecytosol
(9Z,12Z)-octadecadien-1-olReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
3. (9Z,12Z)-octadecadienoyl-CoA + 2 NADPH + 2 H(+) = (9Z,12Z)-octadecadien-1-ol + 2 NADP(+) + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (EPA)
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol
(9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (DPA)
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + malonyl-CoA + H(+) = (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
3-oxooctacosanyol-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (cerotic acid)
3. hexacosanoyl-CoA + malonyl-CoA + H(+) = 3-oxooctacosanyol-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol
3-oxotetracosanoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (behenic acid)
3. very-long-chain 3-oxoacyl-CoA synthase (docosanoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 17 morecytosolOne of 3 routes
3-oxohexacosanoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (lignocerate)
3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 17 morecytosolOne of 3 routes
1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (palmitolate)
3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (palmitolate)
3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (palmitolate)
3. (9Z)-hexadecenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol
(11Z,14Z)-3-oxoicosa-11,14-dienoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
3. (9Z,12Z)-octadecadienoyl-CoA + malonyl-CoA + H(+) = (11Z,14Z)-3-oxoicosa-11,14-dienoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol
(11Z,14Z,17Z)-3-oxoeicosatrienoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (linolenate)
3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + malonyl-CoA + H(+) = (11Z,14Z,17Z)-3-oxoeicosatrienoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosol
3-oxo-(13Z)-docosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)
3. (11Z)-eicosenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(13Z)-docosenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
3-oxo-(15Z)-tetracosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (cis-erucic acid)
3. (13Z)-docosenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(15Z)-tetracosenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
N-(9Z-octadecenoyl)-sphinganineReach from here →
1. ATP:sphinganine 1-phosphotransferase
2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
3. sphinganine + (9Z)-octadecenoyl-CoA = N-(9Z-octadecenoyl)-sphinganine + CoA + H(+)
Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 3 morecytosol
2-hydroxyoctadecanoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (stearate)
3. octadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctadecanoyl-CoA + succinate + CO2
Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol
N-(15Z-tetracosenoyl)-sphinganineReach from here →
1. ATP:sphinganine 1-phosphotransferase
2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
3. (15Z)-tetracosenoyl-CoA + sphinganine = N-(15Z-tetracosenoyl)-sphinganine + CoA + H(+)
Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosolOne of 2 routes
an N-tetracosenoylsphinganineReach from here →
1. ATP:sphinganine 1-phosphotransferase
2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
3. tetracosenoyl-CoA + sphinganine = an N-tetracosenoylsphinganine + CoA + H(+)
Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol
N-hexacosenoylsphinganineReach from here →
1. ATP:sphinganine 1-phosphotransferase
2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
3. hexacosenoyl-CoA + sphinganine = N-hexacosenoylsphinganine + CoA + H(+)
Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol
N-tetracosanoyl-heptadecasphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (lignocerate)
3. heptadecasphing-4-enine + tetracosanoyl-CoA = N-tetracosanoyl-heptadecasphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 10 morecytosol
N-(2-hydroxytetracosenoyl)-sphinganineReach from here →
1. ATP:sphinganine 1-phosphotransferase
2. sphinganine 1-phosphate + H2O = sphinganine + phosphate
3. 2-hydroxytetracosenoyl-CoA + sphinganine = N-(2-hydroxytetracosenoyl)-sphinganine + CoA + H(+)
Catalysed by DBP, SPHK2, SPHK1, SGPP2 and 2 morecytosol
(2E)-hexacosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (cerotic acid)
3. acyl-CoA oxidase (hexacosanoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, peroxisomeOne of 2 routes
3-oxo-(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (DHA)
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
3-oxo-(8Z,11Z,14Z,17Z,20Z,23Z)-hexacosahexaenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)
3. (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z,17Z,20Z,23Z)-hexacosahexaenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
(2S)-2-aminobutanoateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. glycine N-acyltransferase (N-arachidonoylglycine)
3. (2S)-2-aminobutanoate + glyoxylate = 2-oxobutanoate + glycine
Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, mitochondrial matrixOne of 2 routes
N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. acyl-CoA:sphingosine N-acyltransferase
3. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, Golgi apparatus
N-(tetracosenoyl)-sphing-4-enineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. acyl-CoA:sphingosine N-acyltransferase
3. tetracosenoyl-CoA + sphing-4-enine = N-(tetracosenoyl)-sphing-4-enine + CoA + H(+)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 6 morecytosol, Golgi apparatus
1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
3. glycerol-3-phosphate 1-O-acyltransferase (linoleoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 14 morecytosolOne of 2 routes
1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (stearate)
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 15 morecytosol
1-(9Z)-octadecenoyl-2-heptadecanoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (margaric acid)
3. heptadecanoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z)-octadecenoyl-2-heptadecanoyl-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 15 morecytosol
1-(9Z)-octadecenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + (9Z,12Z)-octadecadienoyl-CoA = 1-(9Z)-octadecenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 16 morecytosol
1-octadecanoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (stearate)
3. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 13 morecytosolOne of 2 routes
1-(9Z)-octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (myristic acid)
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-(9Z)-octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 15 morecytosol
3-oxo-(11Z,14Z,17Z,20Z,23Z)-hexacosapentaenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)
3. (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(11Z,14Z,17Z,20Z,23Z)-hexacosapentaenoyl-CoA + CO2 + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
1-(9Z)-octadecenoyl-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. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z,12Z)-octadecadienoyl-CoA = 1-(9Z)-octadecenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
(2E)-eicosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (eicosanoate)
3. acyl-CoA oxidase (eicosanoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, peroxisomeOne of 4 routes
(2E)-docosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (behenic acid)
3. acyl-CoA oxidase (docosanoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, peroxisomeOne of 4 routes
(2E)-tetracosenoyl-CoAReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (lignocerate)
3. acyl-CoA oxidase (tetracosanoyl-CoA)
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol, peroxisomeOne of 3 routes
1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphateReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (palmitolate)
3. (9Z)-hexadecenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphate + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol
1-(9Z-octadecenoyl)-2-(9Z,12Z-octadienoyl)-sn-glycero-3-phospho-L-serineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + (9Z,12Z)-octadecadienoyl-CoA = 1-(9Z-octadecenoyl)-2-(9Z,12Z-octadienoyl)-sn-glycero-3-phospho-L-serine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 12 morecytosol
1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
1. sphingosine N-acyltransferase (sphinganine)
2. long-chain-fatty-acid-CoA ligase (palmitolate)
3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + (9Z)-hexadecenoyl-CoA = 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-L-serine + CoA
Catalysed by CERS1, CERS6, CERS3, CERS5 and 11 morecytosol