a sphingomyelin

Three steps

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5cytosol, extracellular space

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX15cytosol, extracellular space

• 12(S)-HPETEReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 4 routes

• 15(S)-HPETEReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular spaceOne of 4 routes

• 5(S)-HPETEReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by ALOX5cytosol, extracellular space

• betaine aldehydeReach from here →
  1. Sphingomyelin cholinephosphohydrolase
  2. Phosphocholine phosphohydrolase
  3. choline dehydrogenase (choline)

  Catalysed by SMPD2, SMPD1, ENPP7, SMPD4 and 3 morecytosolOne of 3 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• a sterolReach 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-phosphocholine + H2O = a 1-acyl-sn-glycero-3-phosphocholine + a fatty acid + H(+)
  3. a sterol + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sterol ester + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by SGMS1, SGMS2, PLA2G10, PLA2G6 and 29 moreOne of 3 routes

• CHEBI:15978Reach 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 + 2 H2O = sn-glycerol 3-phosphocholine + 2 hexadecanoate + 2 H(+)
  3. sn-Glycero-3-phosphocholine glycerophosphohydrolase

  Catalysed by SGMS2, PLB1, GPCPD1cytosol

• phosphatidylethanolamineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 5 moreendoplasmic reticulum, Golgi apparatus, cytosolOne of 2 routes

• 11-cis-retinyl hexadecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 11-peroxy-docosahexaenoate to DHA conversion

  No catalyst recordedcytosol, extracellular spaceOne of 3 routes

• a 1-O-alkyl-2-acetyl-sn-glycerolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. CDP-choline:1-alkyl-2-acetylglycerol cholinephosphotransferase
  3. CDP-choline:1-alkyl-2-acetylglycerol cholinephosphotransferase

  Catalysed by CHPT1, CEPT1endoplasmic reticulum, cytosolOne of 2 routes

• 11-cis-retinolReach 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. all-trans-retinol--[retinol-binding protein] + a 1,2-diacyl-sn-glycero-3-phosphocholine = apo--[retinol-binding protein] + an all-trans-retinyl ester + a 2-acyl-sn-glycero-3-phosphocholine
  3. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming

  Catalysed by SGMS1, SGMS2, LRAT, RPE65cytosolOne of 3 routes

• phosphatidic acidReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. diacylglycerol cholinephosphotransferase (1,2-diacylglycerol-LD-PC pool)
  3. phosphatidylcholine phosphatidohydrolase

  Catalysed by CHPT1, CEPT1, PLD2, PLD1 and 1 moreendoplasmic reticulum, cytosolOne of 13 routes

• CHEBI:16566Reach from here →
  1. SM pool hydrolysis
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• pregnenoloneReach 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. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by GBA1, GBA2, CYP11A1endoplasmic reticulum

• 1-phosphatidyl-1D-myo-inositolReach 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-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)
  3. ATP:1-Phosphatidyl-1D-myo-inositol 4-phosphotransferase

  Catalysed by SGMS1, SGMS2, OSBPL3, PTPRQ and 12 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• 8-hydroxydodecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxydodecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxytetradecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxytetradecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 12-hydroxytetradecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 11-hydroxytetradecanoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• CHEBI:16856Reach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate and GSH (cytosol to extracellular)

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• psychosineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreendoplasmic reticulum, Golgi apparatus, mitochondrial matrix

• a cholesterol esterReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. diacylglycerol cholinephosphotransferase (1,2-diacylglycerol-LD-PC pool)
  3. Phosphatidylcholine:sterol O-acyltransferase

  Catalysed by CHPT1, CEPT1, LCATendoplasmic reticulum, cytosolOne of 4 routes

• octadecanalReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by ALDH3A2cytosol, extracellular space

• all-trans-retinolReach 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. all-trans-retinol--[retinol-binding protein] + a 1,2-diacyl-sn-glycero-3-phosphocholine = apo--[retinol-binding protein] + an all-trans-retinyl ester + a 2-acyl-sn-glycero-3-phosphocholine
  3. carboxylesterase (retinyl-ester)

  Catalysed by SGMS1, SGMS2, LRAT, CES2 and 19 morecytosolOne of 3 routes

• a 2-acylglycerolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. ceramide:phosphatidylcholine cholinephosphotransferase
  3. a 1,2-diacyl-sn-glycerol + H2O = a 2-acylglycerol + a fatty acid + H(+)

  Catalysed by SGMS1, SGMS2, DAGLB, ABHD11 and 1 moreendoplasmic reticulum, Golgi apparatus

• a monoacylglycerolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. ceramide:phosphatidylcholine cholinephosphotransferase
  3. 1,2-diacyl-sn-glycerol acylhydrolase

  Catalysed by SGMS1, SGMS2, LIPF, LIPC and 13 moreendoplasmic reticulum, Golgi apparatus, extracellular spaceOne of 9 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreendoplasmic reticulum, Golgi apparatus, cytosol

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

  Catalysed by UGCG, GBA1, GBA2endoplasmic reticulumOne of 8 routes

• AH2Reach from here →
  1. Sphingomyelin cholinephosphohydrolase
  2. Phosphocholine phosphohydrolase
  3. choline + A = betaine aldehyde + AH2

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

• 7alpha-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 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, CYP7A1endoplasmic reticulum

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. diacylglycerol cholinephosphotransferase (1,2-diacylglycerol-LD-PC pool)
  3. phosphatidylcholine 2-acylhydrolase

  Catalysed by CHPT1, CEPT1, PLA2G10, PLA2G6 and 16 moreendoplasmic reticulum, cytosolOne of 8 routes

• hexadecanalReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2cytosol, extracellular spaceOne of 3 routes

• 26-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 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, CYP3A4endoplasmic reticulum

• glycerolReach 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-acylglycerol + a 1,3-diacylglycerol = a triacylglycerol + glycerol

  Catalysed by SGMS1, SGMS2, PLA2G15, PNPLA4 and 2 moreOne of 3 routes

• a beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-Cer(d18:1(4E))Reach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. UDP-glucose:N-acylsphingosine D-glucosyltransferase
  3. glucosylceramide pool to LacCer pool conversion

  Catalysed by UGCG, ALG1L2, B4GALT5, B3GALT2 and 32 moreendoplasmic reticulum, cytosolOne of 5 routes

• 4-methylpentanalReach 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. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by GBA1, GBA2, CYP11A1endoplasmic reticulum

• a diacylglycerolReach 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-diacylglycerol + a 1,2-diacyl-sn-glycero-3-phosphocholine = a triacylglycerol + a 1-acyl-sn-glycero-3-phosphocholine
  3. a triacylglycerol + H2O = a diacylglycerol + a fatty acid + H(+)

  Catalysed by SGMS1, SGMS2, TMEM68, DDHD2 and 18 moreOne of 2 routes

• phosphatidyl-L-serineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. diacylglycerol cholinephosphotransferase (1,2-diacylglycerol-LD-PC pool)
  3. phosphatidylserine synthase (PC-LD pool)

  Catalysed by CHPT1, CEPT1, PTDSS1endoplasmic reticulum, cytosol

• cholesteryl 3-beta-D-galactosideReach 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 + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine

  Catalysed by UGT8, GBA1, GBA2endoplasmic reticulumOne of 3 routes

• cholesteryl 3-beta-D-xylosideReach 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. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by GBA1, GBA2, GBA3endoplasmic reticulumOne of 3 routes

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

  Catalysed by ALOX5cytosol, extracellular space

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by UGT1A9, UGT2B7, UGT1A6, UGT1A1 and 2 morecytosol, extracellular space

• (11Z)-docosenoyl-CoA(4-)Reach 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, cytosol

• (7Z)-tetradecenoyl-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, cytosol