(15Z)-tetracosenoate

Three steps

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

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

• (5Z)-octenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 6 routes

• dodecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]

  Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• CHEBI:28701Reach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisomeOne of 7 routes

• 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-(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. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 more

• 12-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes

• cholesteryl hexadecanoateReach 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. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 more

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic 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-(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. ATP:sphingosine 1-phosphotransferase

  Catalysed by ACER2, ACER1, ASAH2, DBP and 2 morecytosolOne of 2 routes

• cholesteryl (9Z,12Z)-octadecadienoateReach 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. (9Z,12Z)-octadecadienoyl-CoA + cholesterol = cholesteryl (9Z,12Z)-octadecadienoate + CoA

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

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

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 moreOne of 3 routes

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

  Catalysed by ACER2, ACER1, ASAH2, GBA1

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, peroxisome, endoplasmic reticulumOne of 3 routes

• N-(acetyl)-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. 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, PAFAH2One of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic 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 (nervonic 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-(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. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 more

• taurineReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 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 (nervonic 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 2 routes

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

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

• 3'-dephospho-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, lysosomeOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 9 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 13 routes

• glutaryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Production of Glutaryl Carnitine

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 19 routes

• itaconyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Itaconate:CoA ligase (GDP-forming)

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 21 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 16 routes

• octanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. phytanate-CoA ligase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 5 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 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