dodecanoate

Three steps

• phosphatidic acidReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. carnitine O-palmitoyltransferase (dodecanoylcarnitine)
  3. dodecanoyl-CoA + (R)-carnitine = O-dodecanoyl-R-carnitine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• oxaloacetateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. ATP citrate lyase (citrate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:16566Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

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

• pregnenoloneReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• 9-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

  Catalysed by NAAA, ASAH1, ACER2, ASAH2cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. glycerol-3-phosphate 1-O-acyltransferase (lauroyl-CoA)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• a cholesterol esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + cholesterol = a cholesterol ester + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

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

  Catalysed by ALDH3A2cytosol, extracellular space

• anilineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol

• CHEBI:17312Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• cholesteryl 3-beta-D-glucosideReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreOne of 8 routes

• 7alpha-hydroxycholesterolReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• L-cysteineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrix

• hexadecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 2 routes

• 26-hydroxycholesterolReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix

• a 1,2-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 3 routes

• a triacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:17927Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• 4-methylpentanalReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• cholesteryl 3-beta-D-galactosideReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreOne of 3 routes

• cholesteryl 3-beta-D-xylosideReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-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 NAAA, ASAH1, ACER2, ASAH2 and 3 moreOne of 2 routes

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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

• (5Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 4 routes

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 6 routes

• (7Z)-tetradecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 10 routes

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

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

  Catalysed by FAAHcytosol, extracellular space

• CHEBI:27540Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 6 routes

• decanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. Decanoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• CHEBI:28701Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisomeOne of 7 routes

• O-decanoyl-(R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. decanoyl-CoA + (R)-carnitine = O-decanoyl-(R)-carnitine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrix

• a fatty acidReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

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

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 2 routes

• (24S)-hydroxycholesterolReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• cholesteryl hexadecanoateReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• sphingosine 1-phosphateReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 morecytosolOne of 2 routes

• cholesteryl (9Z,12Z)-octadecadienoateReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. (9Z,12Z)-octadecadienoyl-CoA + cholesterol = cholesteryl (9Z,12Z)-octadecadienoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 moreOne of 2 routes