octadecanoate

Three steps

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

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

• (2E)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-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 (stearate)
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 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 (stearate)
  2. Stearoyl-CoA hydrolase
  3. Butanoate:CoA ligase (AMP-forming)

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 13 routes

• glutaryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-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 (stearate)
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 19 routes

• itaconyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-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 (stearate)
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 23 routes

• tetradecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 18 routes

• octanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. Beta Oxidation Fatty Acid

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, mitochondrial matrixOne of 24 routes

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

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

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisome

• a 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  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 4 morecytosol

• ethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + L-serine = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + ethanolamine

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

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  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 4 morecytosolOne of 2 routes

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

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

• sphinganineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)
  3. N-(octadecanoyl)-sphinganine + H2O = sphinganine + octadecanoate

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

• spermidineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-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 (stearate)
  2. Stearoyl-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 (stearate)
  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 5 morecytosol

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  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 7 morecytosol

• L-alanineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-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 (stearate)
  2. Stearoyl-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 (stearate)
  2. Stearoyl-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-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-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 ASAH1, ACER2, ASAH2, GBA1 and 1 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-acyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

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

• 3-oxosphinganineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

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

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. glyceronephosphate O-acyltransferase (DHAP)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)Reach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-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 ASAH1, ACER2, ASAH2, GBA1 and 2 moreinner side of the membrane, outer side of the membraneOne of 2 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 16 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• sphing-4-enine 1-phosphateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, SPHK2 and 1 more

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  No catalyst recordedcytosol, extracellular space

• decanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 9 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. Fatty Acid Beta Oxidation (C18:1->C16:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 21 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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