(11Z,14Z)-eicosadienoate

Three steps

• 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 ((11Z,14Z)-eicosadienoic 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 ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

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

• 3'-dephospho-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

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

• (2E)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 10 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• butanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. Butanoate:CoA ligase (AMP-forming)

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

• dodecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 13 routes

• glutaryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. Production of Glutaryl Carnitine

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

• eicosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 19 routes

• itaconyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. Itaconate:CoA ligase (GDP-forming)

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

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 19 routes

• tetradecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 16 routes

• octanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 20 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 ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. phytanate-CoA ligase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 5 routes

• octadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 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 ((11Z,14Z)-eicosadienoic 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 ((11Z,14Z)-eicosadienoic 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 ((11Z,14Z)-eicosadienoic 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

• sphing-4-enineReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, Golgi apparatusOne of 2 routes

• 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 ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic 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 ((11Z,14Z)-eicosadienoic 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 ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

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

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• (3Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  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 17 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 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

• (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 ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 6 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)
  2. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 17 routes