N-(9Z-octadecenoyl)-L-leucine

Three steps

• L-2-aminohexanoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Transport of L-Kynurenine
  3. 2-oxohexanoate + L-kynurenine = L-2-aminohexanoate + kynurenate + H2O

  Catalysed by PM20D1, SLC43A1, AADATextracellular space, cytosol

• 5-guanidino-2-oxopentanoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of arginine and leucine (cytosol to extracellular)
  3. L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + H2O2 + NH4(+)

  Catalysed by PM20D1, SLC3A2, SLC7A6, SLC7A7 and 1 moreextracellular space, cytosol

• (3Z)-dodecenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by PM20D1, HADHA, ACAA2, HADHBmitochondrial matrixOne of 3 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• S-sulfanyl-L-cysteineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of cysteine and leucine (cytosol to extracellular)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by PM20D1, SLC7A9, SLC3A1, CARS2extracellular space, cytosol

• N-formyl-L-kynurenineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of leucine and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 = N-formyl-L-kynurenine

  Catalysed by PM20D1, SLC7A5, IDO1, TDO2 and 1 moreextracellular space, cytosolOne of 2 routes

• L-2-aminoadipateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Transport of L-Kynurenine
  3. 2-oxoadipate + L-kynurenine = L-2-aminoadipate + kynurenate + H2O

  Catalysed by PM20D1, SLC43A1, AADATextracellular space, cytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by PM20D1, SLC27A2, SLC27A5mitochondrial matrix, endoplasmic reticulumOne of 3 routes

• 5-phospho-beta-D-ribosylamineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of glutamine and leucine (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by PM20D1, SLC7A5, PPATextracellular space, cytosolOne of 2 routes

• D-glucosamine 6-phosphateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of glutamine and leucine (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by PM20D1, SLC7A5, GFPT2, GFPT1extracellular space, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of leucine and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by PM20D1, SLC3A2, SLC7A5, MSRAextracellular space, cytosol

• L-methionine (R)-S-oxideReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of leucine and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by PM20D1, SLC3A2, SLC7A5, MSRB3 and 2 moreextracellular space, cytosol

• 5-amino-2-oxopentanoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of leucine and ornithine (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by PM20D1, SLC7A6, AGXT2extracellular space, cytosolOne of 2 routes

• deoxycholoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by PM20D1, SLC27A2, SLC27A5mitochondrial matrix, cytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of glycine and leucine (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosolOne of 2 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of cysteine and leucine (cytosol to extracellular)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by PM20D1, SLC7A9, SLC3A1, PPCSextracellular space, cytosolOne of 4 routes

• 2-hydroxy-4-methylvaleric acidReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. L-Leucine:2-oxoglutarate aminotransferase
  3. 4-methyl-2-oxopentanoate reduction

  Catalysed by PM20D1, BCAT2, SDR42E2, AKR1B15 and 16 moremitochondrial matrix, cytosol

• an L-alpha-amino acidReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Transport of L-Kynurenine
  3. an L-alpha-amino acid(in) + L-kynurenine(out) = an L-alpha-amino acid(out) + L-kynurenine(in)

  Catalysed by PM20D1, SLC43A1, SLC7A11extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-aminobutanoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of chloride and leucine (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by PM20D1, SLC6A14, SLC6A12extracellular space, cytosolOne of 4 routes

• 3-iodo-L-tyrosineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of leucine and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by PM20D1, SLC7A5, TPOextracellular space, cytosolOne of 2 routes

• dopamineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. solute carrier (L-dopa)
  3. 3,4-Dihydroxy-L-phenylalanine carboxy-lyase

  Catalysed by PM20D1, SLC3A2, SLC7A5, DDCextracellular space, cytosol

• L-prolineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of alanine and leucine (cytosol to extracellular)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by PM20D1, SLC7A5, SLC1A4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-benzoylglycineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of glycine and leucine (cytosol to extracellular)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by PM20D1, SLC7A5extracellular space, cytosol, mitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of cysteine and leucine (cytosol to extracellular)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by PM20D1, SLC7A9, SLC3A1, CDO1extracellular space, cytosolOne of 6 routes

• decanoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by PM20D1, ACSM4, ACSM1, ACSM2A and 3 moremitochondrial matrix, cytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. Carnitine O-Palmitoyltransferase

  Catalysed by PM20D1, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• L-cysteinylglycineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of alanine and leucine (cytosol to extracellular)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by PM20D1, SLC7A5, GGTLC3, GGT1 and 4 moreextracellular space, cytosolOne of 2 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by PM20D1, CPT1A, CPT1Bmitochondrial matrix, cytosol

• CHEBI:63544Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 7 routes

• sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by PM20D1, ABHD12One of 2 routes

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 14 more

• hexacosanoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 5 routes

• tetracosanoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 10 routes

• docosanoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 9 routes

• all-trans-retinyl 9Z-octadecenoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

  Catalysed by PM20D1, DGAT1, LIPA, PNPLA4 and 2 more

• N(5)-[(Z)-amino(hydroxyimino)methyl]ornithineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of arginine and leucine (cytosol to extracellular)
  3. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)

  Catalysed by PM20D1, SLC3A2, SLC7A6, SLC7A7 and 3 moreextracellular space, cytosol

• Mo-molybdopterinReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. transport of alanine and leucine (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by PM20D1, SLC7A5, MOCOSextracellular space, cytosol

• (2E)-octadecenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. Carnitine O-Palmitoyltransferase

  Catalysed by PM20D1, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 8 routes

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 13 routes

• 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by PM20D1, ABHD12, LPGAT1

• 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. 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(+)
  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 PM20D1, ABHD16A

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 7 more

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 7 more

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 10 more

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 7 more

• (9Z)-octadecen-1-olReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. (9Z)-octadecenoyl-CoA + 2 NADPH + 2 H(+) = (9Z)-octadecen-1-ol + 2 NADP(+) + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 6 more

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. Acetylation of Leucine
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 6 routes