an N-acylsphing-4-enine

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

723 compounds within 3 steps: 17 in 1, 168 in 2, 538 in 3

Three steps

7-hydroxydodecanoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 7-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by ASAH1, CYP4Z1lysosome, extracellular space
N-(dodecanoyl)-sphinganineReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. N-(dodecanoyl)-sphinganine + H2O = dodecanoate + sphinganine
Catalysed by ASAH1lysosome, extracellular space
N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. 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(+)
3. N-(acetyl)-sphing-4-enine + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus
24S,25-dihydroxycholesterolReach from here →
1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 24S,25-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by GBA1, GBA2, CYP46A1
(24S,25R)-24,26-dihydroxycholesterolReach from here →
1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by GBA1, GBA2, CYP46A1
N-tetradecanoylglycineReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol
(2R,6)-dimethylheptanoyl-CoAReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 7 moreGolgi apparatus, mitochondrial matrix
N-eicosanoylglycinateReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol
N-docosanoylglycineReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol
N-hexacosanoylglycineReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol
(2E,5Z)-tetradecadienoyl-CoAReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreGolgi apparatus, cytosol, mitochondrial matrixOne of 4 routes
(2E,7Z)-hexadecadienoyl-CoAReach from here →
1. acyl-CoA:sphingosine N-acyltransferase
2. acyl-CoA pool formation and breakdown
3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreGolgi apparatus, cytosol, mitochondrial matrixOne of 4 routes
(12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
Catalysed by ASAH1, ALOX12lysosome, extracellular space
(18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by ASAH1, CYP4F8lysosome, extracellular space
17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
Catalysed by ASAH1, PTGS2lysosome, extracellular space
13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O
Catalysed by ASAH1, PTGS2lysosome, extracellular space
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. prostaglandin-endoperoxide synthase (EPA)
Catalysed by ASAH1, PTGS1, PTGS2lysosome, extracellular space, cytosolOne of 2 routes
(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O
Catalysed by ASAH1, PTGS2lysosome, extracellular space
(11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O
Catalysed by ASAH1, PTGS2lysosome, extracellular space
15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by ASAH1, ALOX15Blysosome, extracellular space
5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
Catalysed by ASAH1, ALOX15Blysosome, extracellular space
13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
1. N-Acylsphingosine amidohydrolase
2. (10Z)-heptadecenoic acid formation
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O
Catalysed by ASAH1, PTGS2lysosome, extracellular space
an N-acetyl-alpha-neuraminosyl-(2->8)-N-acetyl-alpha-neuraminosyl-(2->3)-beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach from here →
1. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)
2. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + CMP-N-acetyl-beta-neuraminate = a ganglioside GM4 (d18:1(4E)) + CMP + H(+)
3. a ganglioside GM4 (d18:1(4E)) + CMP-N-acetyl-beta-neuraminate = an N-acetyl-alpha-neuraminosyl-(2->8)-N-acetyl-alpha-neuraminosyl-(2->3)-beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + CMP + H(+)
Catalysed by UGT8, ST3GAL5, ST8SIA6