a sphingomyelin

Three steps

• S-hexadecanoyl-N-acetylcysteamineReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 2-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteamine + H2O = N-acetylcysteamine + hexadecanoate + H(+)

  Catalysed by SGMS2, PLAAT3, PLA2G15, PLAAT1 and 4 more

• S-hexadecanoyl-N-acetylcysteine methyl esterReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 2-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by SGMS2, PLAAT3, PLA2G15, PLAAT1 and 3 more

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. fatty acylamide amidohydrolase

  Catalysed by FAAHcytosol, extracellular space

• dodecanalReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]

  Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• alpha-D-galactoseReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. UDP-alpha-D-galactose:N-acylsphingosine D-galactosyltransferase
  3. D-galactosyl-N-acylsphingosine galactohydrolase

  Catalysed by UGT8, GALCendoplasmic reticulum, cytosol, lysosome

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SGMS2, PLA2G10, PLA2G6, PLA2G1B and 12 more

• chlorine(.)Reach from here →
  1. Sphingomyelin cholinephosphohydrolase
  2. Phosphocholine phosphohydrolase
  3. transport of chloride and choline (cytosol to extracellular)

  Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 3 morecytosol, extracellular space

• acetateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. CDP-choline:1-alkyl-2-acetylglycerol cholinephosphotransferase
  3. 1-Alkyl-2-acetyl-sn-glycero-3-phosphocholine acetohydrolase

  Catalysed by CHPT1, CEPT1, PAFAH1B1, PAFAH1B2 and 3 moreendoplasmic reticulum, cytosolOne of 5 routes

• (9Z,12Z)-octadecadienoateReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 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
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + H2O = (9Z,12Z)-octadecadienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SGMS2, TAFAZZIN, PLA2G6, LCAT and 11 more

• a 1-O-alkyl-sn-glycero-3-phosphocholineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. diacylglycerol cholinephosphotransferase (1-alkyl-2-acylglycerol)
  3. a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholine + H2O = a 1-O-alkyl-sn-glycero-3-phosphocholine + a fatty acid + H(+)

  Catalysed by CHPT1, CEPT1, PLA2G6, PLA2G4A and 4 moreendoplasmic reticulum, cytosolOne of 8 routes

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. ceramide:phosphatidylcholine cholinephosphotransferase
  3. an N-acyl-(4R)-4-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-(4R)-4-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by SGMS1, SGMS2endoplasmic reticulum, Golgi apparatusOne of 4 routes

• (24S)-hydroxycholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, CYP46A1endoplasmic reticulum

• an acylcholineReach from here →
  1. Sphingomyelin cholinephosphohydrolase
  2. Phosphocholine phosphohydrolase
  3. an acylcholine + H2O = a carboxylate + choline + H(+)

  Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 3 morecytosol

• a fatty aldehydeReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. an N-acylsphing-4-enine + H2O = sphing-4-enine + a fatty acid
  3. a fatty aldehyde + NAD(+) + H2O = a fatty acid + NADH + 2 H(+)

  Catalysed by NAAA, ASAH1, ACER2, ACER1 and 3 moreendoplasmic reticulum

• a 1-acylglycerolReach from here →
  1. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol
  2. a 3-acyl-sn-glycerol + a 1,2-diacyl-sn-glycero-3-phosphocholine = a 1,3-diacylglycerol + a 1-acyl-sn-glycero-3-phosphocholine
  3. a 1,3-diacylglycerol + H2O = a 1-acylglycerol + a fatty acid + H(+)

  Catalysed by SGMS1, SGMS2, PLA2G15, DDHD2 and 1 moreOne of 2 routes

• 12-hydroxydodecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes

• cholesteryl hexadecanoateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA

  Catalysed by GBA1, GBA2, SOAT1endoplasmic reticulum

• sphingosine 1-phosphateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreendoplasmic reticulum, Golgi apparatus, cytosolOne of 2 routes

• D-galactoseReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)
  3. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + H2O = D-galactose + an N-acylsphing-4-enine

  Catalysed by UGT8, GBA1, GALC, GBA3 and 1 moreendoplasmic reticulum

• cholesteryl (9Z,12Z)-octadecadienoateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. (9Z,12Z)-octadecadienoyl-CoA + cholesterol = cholesteryl (9Z,12Z)-octadecadienoate + CoA

  Catalysed by GBA1, GBA2, SOAT1endoplasmic reticulumOne of 3 routes

• D-glucoseReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. UDP-glucose:N-acylsphingosine D-glucosyltransferase
  3. D-Glucosyl-N-acylsphingosine glucohydrolase

  Catalysed by UGCG, GBA1, GBA3, GBA2endoplasmic reticulum, cytosolOne of 5 routes

• 25-hydroxycholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by GBA1, GBA2, CH25Hendoplasmic reticulumOne of 3 routes

• 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineReach from here →
  1. a sphingomyelin + H2O = phosphocholine + an N-acylsphing-4-enine + H(+)
  2. phosphocholine + CTP + H(+) = CDP-choline + diphosphate
  3. 1-O-hexadecyl-2-acetyl-sn-glycerol + CDP-choline = 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + CMP + H(+)

  Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 4 more

• N-octanoylsphing-4-enineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by GBA1, GBA2endoplasmic reticulum

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA

  Catalysed by GBA1, GBA2, SOAT2, SOAT1endoplasmic reticulumOne of 2 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  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 ASAH1, ACER2, ACER1, ASAH2 and 1 moreendoplasmic reticulum, Golgi apparatusOne of 2 routes

• (24R)-hydroxycholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, CYP3A4endoplasmic reticulum

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. fatty acid amide hydrolase (2-arachidonoylglycerol)

  Catalysed by FAAHcytosol, extracellular space

• an N-acylethanolamineReach from here →
  1. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol
  2. a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 2-acyl-sn-glycero-3-phosphocholine + H(+)
  3. an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine + H2O = an N-acylethanolamine + a 1,2-diacyl-sn-glycero-3-phosphate + H(+)

  Catalysed by SGMS1, SGMS2, PLA2G4E, PLAAT5 and 2 more

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O

  Catalysed by DGAT1, LIPA, PNPLA4, LIPE and 1 morecytosol, extracellular space

• 16-hydroxyhexadecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. a sphingomyelin + H2O = phosphocholine + an N-acylsphing-4-enine + H(+)
  2. phosphocholine + CTP + H(+) = CDP-choline + diphosphate
  3. 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + CDP-choline = 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CMP + H(+)

  Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 4 more

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 2 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, extracellular space

• dodecanoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 4 routes

• hexadecanoyl-CoAReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 2-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
  3. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate

  Catalysed by SGMS2, PLAAT3, PLA2G15, PLAAT1 and 13 more

• eicosanoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 7 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 6 routes

• tetradecanoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 5 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 4 morecytosol, extracellular space

• octadecanoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 7 routes

• prostaglandin H2Reach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. prostaglandin-endoperoxide synthase (arachidonate)

  Catalysed by PTGS1, PTGS2cytosol, extracellular spaceOne of 3 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by ALOX5, ALOX15, ALOX12cytosol, extracellular space

• (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by ALOX15B, ALOX15, ALOX12cytosol, extracellular space

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by ALOX5cytosol, extracellular space

• leukotriene A4Reach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

  Catalysed by ALOX5cytosol, extracellular space

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular space

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + choline + H(+)

  Catalysed by SGMS2, PLA2G10, PLA2G6, PLA2G1B and 14 moreOne of 2 routes

• a 1-acylglycerone 3-phosphateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreendoplasmic reticulum, Golgi apparatus

• (R)-2-hydroxyoctadecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space