linoleic acid

Three steps

• CHEBI:18095Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of trans-4-hydroxy-L-proline (cytosol to extracellular)

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular space

• N-carbamoyl-beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of 3-Ureidopropionate

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

  Catalysed by ALOX5cytosol, extracellular space

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, MOGAT2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. Beta Oxidation of Fatty Acid
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• O-butanoyl-(R)-carnitineReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, CRATendoplasmic reticulum, cytosol, mitochondrial matrix

• (5Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by UGT1A9, UGT2B7, UGT1A6, UGT1A1 and 2 morecytosol, extracellular space

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

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

• (7Z)-tetradecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

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

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 3 routes

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. fatty acyl-CoA desaturase (N-C18:2CoA -> N-C18:3CoA)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• CHEBI:240943Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. 2-Methylbutyrylglycine Transport, Extracellular

  Catalysed by SLC6A14, SLC6A5endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• hypochlorous acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Peroxidase

  Catalysed by SLC6A14, LPOendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• octanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. Beta Oxidation of Fatty Acid
  3. Octanoyl-CoA hydrolase

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

• potassium atomReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC12A2, SLC12A1endoplasmic reticulum, cytosol, extracellular spaceOne 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 (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 15 morecytosolOne of 7 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 (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 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

• formic acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by SLC6A14, SLC26A4endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• propionic acidReach from here →
  1. Utilized Transport
  2. Active Transport
  3. Propanoyl-CoA hydrolase

  Catalysed by ACOT7endoplasmic reticulum, cytosol, mitochondrial matrixOne of 3 routes

• butyric acidReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. Butyryl-CoA hydrolase

  Catalysed by SLC33A1, ESCO2, OXSM, ACOT12endoplasmic reticulum, cytosol, mitochondrial matrix

• malonic acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Malonate Transport, Antiport with Chloride

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• 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

• methylarsonateReach from here →
  1. linoleate:oxygen 9-oxidoreductase
  2. (9S)-hydroperoxy-(10E,12Z)-octadecadienoate + 2 glutathione = (9S)-hydroxy-(10E,12Z)-octadecadienoate + glutathione disulfide + H2O
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by GPX1, GPX4, GSTO1, GSTO2cytosol

• thiosulfateReach from here →
  1. linoleate:oxygen 9-oxidoreductase
  2. (9S)-hydroperoxy-(10E,12Z)-octadecadienoate + 2 glutathione = (9S)-hydroxy-(10E,12Z)-octadecadienoate + glutathione disulfide + H2O
  3. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by GPX1, GPX4, TSTD1cytosol

• 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

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  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

• a 1,3-diacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  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 (linoleate)
  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

• taurineReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 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 5 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 (linoleate)
  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 (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 14 routes

• (R)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

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

• (S)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

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

• 3'-dephospho-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

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

• (2E)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. (2E)-dodecenoyl-CoA formation

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

• (2E)-butenoyl-CoAReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase

  Catalysed by SLC33A1, ESCO2, OXSM, ACADS and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (linoleate)
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

• acryloyl-CoAReach from here →
  1. Utilized Transport
  2. Active Transport
  3. medium-chain acyl-CoA dehydrogenase (propanoyl-CoA)

  Catalysed by ACADS, ACADSBendoplasmic reticulum, cytosol, mitochondrial matrix

• (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