(9Z)-octadecenoate

Three steps

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

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

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

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

• cholesteryl (7Z)-octadecenoateReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• (7Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 5 routes

• CHEBI:15345Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Acetoacetate:CoA ligase (AMP-forming)

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

• cholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Acetyl-CoA:choline O-acetyltransferase

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

• 4a-hydroxytetrahydrobiopterinReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase(4-hydroxylating)

  Catalysed by PM20D1, PAHcytosol

• CHEBI:15380Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• 2-methylcrotonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Production of Tiglylcarnitine

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

• isobutyryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

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

• isovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 15 routes

• CHEBI:15519Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. propanoyl-CoA C-acyltransferase

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

• palmitoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 20 routes

• phenylacetyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Phenylacetate:CoA ligase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 3 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

• (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine

  Catalysed by PM20D1, PAH

• CHEBI:15650Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 39 morecytosolOne of 2 routes

• CHEBI:15699Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. transport of homoserine and phenylalanine (cytosol to extracellular)

  Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 6 routes

• CHEBI:15727Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

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

• CHEBI:15746Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. diamine N-acetyltransferase (N1-acetylspermine)

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

• CHEBI:15765Reach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  3. solute carrier (L-dopa)

  Catalysed by PM20D1, SLC3A2, SLC7A5extracellular space, cytosol

• 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  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 spaceOne of 5 routes

• CHEBI:15978Reach from here →
  1. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  3. 1-(sn-glycero-3-phospho)-1D-myo-inositol glycerophosphohydrolase

  Catalysed by ABHD12, GDE1cytosol

• phosphatidylethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  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 (oleate)
  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

• L-cystineReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  3. Transport of L-Cystine (L-Leucine antiport) by B0, +At Transporter

  Catalysed by PM20D1, SLC7A9, SLC3A1extracellular space, cytosol

• 11-cis-retinolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol

• phosphatidic acidReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  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 9 routes

• L-citrullineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. transport of citrulline and phenylalanine (cytosol to extracellular)

  Catalysed by PM20D1, SLC7A6extracellular space, cytosolOne of 4 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 11 routes

• oxaloacetateReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. ATP citrate lyase (citrate)

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

• 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 12 routes

• protein polypeptide chainReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. PROTEIN_BS

  Catalysed by PM20D1cytosolOne of 2 routes

• 2-phenylacetamideReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine:oxygen 2-oxidoreductase (decarboxylating)

  Catalysed by PM20D1, EPXcytosol

• 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 morecytosolOne of 3 routes

• pregnenoloneReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• N-[(S)-lactoyl]-L-phenylalanineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O

  Catalysed by PM20D1, CNDP2

• 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