dodecanoate

Three steps

• 25-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 + AH2 + O2 = 25-hydroxycholesterol + A + H2O

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

• N-octanoylsphing-4-enineReach 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. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 more

• cholesteryl (9Z-octadecenoate)Reach 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 + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 4 moreOne of 2 routes

• N-(acetyl)-sphing-4-enineReach 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. 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 NAAA, ASAH1, ACER2, ASAH2 and 1 morecytosolOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• a 1,2-diacylglycerolReach 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-diacylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes

• (24R)-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 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• taurineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

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

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

  Catalysed by FAAHcytosol, extracellular space

• an N-acylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. delta 4-desaturase, sphingolipid (dihydroceramide pool)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 9 routes

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

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

• glycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

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

• (R)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

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

• (S)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

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

• 3'-dephospho-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

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

• 3-oxohexadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecanoyl-CoA + malonyl-CoA + H(+) = 3-oxohexadecanoyl-CoA + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

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

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  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

• butanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 9 routes

• glutaryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Production of Glutaryl Carnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 2 routes

• eicosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 19 routes

• itaconyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Itaconate:CoA ligase (GDP-forming)

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

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 19 routes

• octanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 21 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  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

• phytanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. phytanate-CoA ligase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 5 routes

• octadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 22 routes

• prostaglandin H2Reach from here →
  1. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  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. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular space

• a 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• (R)-2-hydroxyoctadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• an N-acylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

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

• sphinganineReach 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

• spermidineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 3 routes

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

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

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

• L-alanineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

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

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach 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 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)Reach 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 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(in) + cholesterol(out)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 4 moreinner side of the membrane, outer side of the membraneOne of 2 routes