(15Z)-tetracosenoate

Three steps

• (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 (nervonic 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 (nervonic 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 (nervonic 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic 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 (nervonic 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

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

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 ACER2, ACER1, ASAH2, GBA1 and 1 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-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 ACER2, ACER1, 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 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-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ACER2, ACER1, 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 17 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  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 5 morecytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• an all-trans-retinyl esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

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

• CHEBI:63544Reach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

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

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CYP4F8cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  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 ACER2, ACER1, ASAH2, PAFAH2

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

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

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

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

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

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

• hexacosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 9 routes

• tetracosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 18 routes

• docosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

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

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

• (22R)-hydroxycholesterolReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (22R)-hydroxycholesterol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 moreOne of 2 routes

• (2E)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 9 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD12cytosol, extracellular space

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• N-dodecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 4 routes

• N-tetradecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 2 routes

• N-hexadecanoylsphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  3. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)

  Catalysed by ACER2, ACER1, ASAH2, CERS6 and 3 moreOne of 3 routes

• N-octadecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 4 routes

• N-eicosanoyl-sphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  3. eicosanoyl-CoA + sphing-4-enine = N-eicosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by ACER2, ACER1, ASAH2, TLCD3B and 1 more