(8Z,11Z,14Z)-eicosatrienoate

Three steps

• 2-methylcrotonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Production of Tiglylcarnitine

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

• isobutyryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

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

• 3-methylbut-2-enoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

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

• isovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. glycine N-acyltransferase (isovalerylglycine)

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

• CHEBI:15519Reach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase

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

• palmitoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Palmitate:CoA ligase (AMP-forming)

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

• oleoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 15 routes

• phenylacetyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Phenylacetate:CoA ligase

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

• L-leucineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and leucine (cytosol to extracellular)

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

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5cytosol, extracellular space

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX15cytosol, extracellular space

• 12(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 4 routes

• 15(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular spaceOne of 4 routes

• 5(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by ALOX5cytosol, extracellular space

• CHEBI:15650Reach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 41 morecytosolOne of 2 routes

• S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheineReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. (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
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + H2O = S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• betaine aldehydeReach from here →
  1. (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1
  2. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by PTGS2, CHDH

• CHEBI:15727Reach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

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

• CHEBI:15746Reach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

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

• 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• CHEBI:15971Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and histidine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular space

• phosphatidylethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

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

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

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

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

  Catalysed by SLC6A14, SLC26A6endoplasmic reticulum, cytosol, extracellular space

• 11-cis-retinyl hexadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 11-peroxy-docosahexaenoate to DHA conversion

  No catalyst recordedcytosol, extracellular spaceOne of 3 routes

• 11-cis-retinolReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosol

• phosphatidic acidReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. Utilized Transport
  2. solute carrier (L-carnitine)
  3. O-octanoyl-(R)-carnitine(in) + (R)-carnitine(out) = O-octanoyl-(R)-carnitine(out) + (R)-carnitine(in)

  Catalysed by SLC25A20endoplasmic reticulum, cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 8 routes

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

  Catalysed by SLC6A14, SLC26A4endoplasmic reticulum, cytosol, extracellular space

• L-valineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and valine (cytosol to extracellular)

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

• oxaloacetateReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. ATP citrate lyase (citrate)

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

• L-arginineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of arginine and chloride (cytosol to extracellular)

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

• CHEBI:16566Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• 8-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 12-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 11-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• formaldehydeReach from here →
  1. (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1
  2. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O
  3. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by PTGS2, KDM1A, KDM1BOne of 3 routes

• CHEBI:16856Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate and GSH (cytosol to extracellular)

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• CHEBI:16857Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Threonine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular space

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

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

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

  Catalysed by SLC6A14, SLC26A6endoplasmic reticulum, cytosol, extracellular space

• a cholesterol esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, endoplasmic reticulumOne of 4 routes

• octadecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by ALDH3A2cytosol, extracellular space

• L-isoleucineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and isoleucine (cytosol to extracellular)

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

• CHEBI:17203Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Proline by the Apical Imino Amino Acid Transporters

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• anilineReach from here →
  1. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  2. Dihomo-gamma-linolenoyl-CoA hydrolase
  3. Acetyl-CoA:arylamine N-acetyltransferase

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