a sphingomyelin
362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API
427 compounds within 3 steps: 8 in 1, 81 in 2, 338 in 3
Three steps
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1cytosol, extracellular space
- ceramide cholinephosphotransferase (CDP-choline)
- acyl-CoA:sphingosine N-acyltransferase
- an acyl-CoA + H2O = an acyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreendoplasmic reticulum, Golgi apparatus
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- DHA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 21-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate[r]
Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- myristic acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 13-hydroxytetradecanoate[r]
Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O
Catalysed by PTGS2cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1
Catalysed by PTGS2cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 O2 = prostaglandin G3
Catalysed by PTGS2cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + O2 = 14-hydroperoxy-(7Z,10Z,12E,16Z,19Z)-docosapentaenoate
Catalysed by ALOX15cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate
Catalysed by ALOX15cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate
Catalysed by ALOX15cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- transport of arachidonate (cytosol to extracellular)
Catalysed by SLCO1B1cytosol, extracellular spaceOne of 2 routes
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
Catalysed by PM20D1cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
Catalysed by PM20D1cytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 3 morecytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP1A1, CYP3A4, CYP2C8, CYP2D6 and 2 morecytosol, extracellular space
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes
- ceramide cholinephosphotransferase (CDP-choline)
- a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
- cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)
Catalysed by GBA1, GBA2, SULT2B1, SULT1C2endoplasmic reticulum
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by CYP2C9cytosol, extracellular space
- ceramide cholinephosphotransferase (CDP-choline)
- an N-acylsphing-4-enine + H2O = sphing-4-enine + a fatty acid
- a 3-(acyloxy)acyl derivative of bacterial toxin + H2O = a 3-hydroxyacyl derivative of bacterial toxin + a fatty acid + H(+)
Catalysed by NAAA, ASAH1, ACER2, ACER1 and 3 moreendoplasmic reticulum
- 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
- 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)
- 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + H2O = 1-O-(1Z-octadecenyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + (9Z)-octadecenoate + H(+)
Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular space
- ceramide cholinephosphotransferase (CDP-choline)
- a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
- 1-hexadecanoyl-2-(11Z,14Z,17Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = (11Z,14Z,17Z-eicosatrienoyl)-cholesterol + 1-hexadecanoyl-sn-glycero-3-phosphocholine
- 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
- 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)
- 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + H2O = 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + N-hexadecanoylethanolamine + H(+)
- 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
- 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
- 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
No catalyst recordedcytosol, extracellular spaceOne of 2 routes
- SM pool hydrolysis
- (10Z)-heptadecenoic acid formation
- 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)
Catalysed by DAGLBcytosol, extracellular space
- 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
- 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine
- 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine = 1-O-(1Z-alkenyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine
- ceramide cholinephosphotransferase (CDP-choline)
- acyl-CoA:sphingosine N-acyltransferase
- acyl-CoA pool formation and breakdown
Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosol
- Sphingomyelin cholinephosphohydrolase
- Phosphocholine phosphohydrolase
- Acetyl-CoA:choline O-acetyltransferase
Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 3 morecytosolOne of 3 routes
- ceramide cholinephosphotransferase (CDP-choline)
- acyl-CoA:sphingosine N-acyltransferase
- acyl-CoA pool formation and breakdown
Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 4 routes
- ceramide cholinephosphotransferase (CDP-choline)
- acyl-CoA:sphingosine N-acyltransferase
- acyl-CoA pool formation and breakdown
Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 4 routes
- ceramide cholinephosphotransferase (CDP-choline)
- acyl-CoA:sphingosine N-acyltransferase
- acyl-CoA pool formation and breakdown
Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 4 routes