(9Z)-octadecenoate

Three steps

• 3'-dephospho-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. acid phosphatase 2, lysosomal (CoA)

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 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 (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 12 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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 17 routes

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

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

• hexadecanoyl-CoAReach from here →
  1. Utilized Transport
  2. palmitoyl-CoA:L-carnitine O-palmitoyltransferase
  3. (R)-carnitine + hexadecanoyl-CoA = O-hexadecanoyl-(R)-carnitine + CoA

  Catalysed by CPT2, CPT1A, CPT1Bendoplasmic reticulum, cytosol, peroxisomeOne of 3 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 19 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 16 routes

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

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

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

  Catalysed by ALOX5cytosol, extracellular space

• leukotriene A4Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

  Catalysed by ALOX5cytosol, extracellular space

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular space

• L-dopaReach 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-dopa(out) + L-phenylalanine(in) = L-dopa(in) + L-phenylalanine(out)

  Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 14 more

• a 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

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

• (R)-2-hydroxyoctadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space

• L-histidineReach 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-histidine(in) + L-phenylalanine(out) = L-histidine(out) + L-phenylalanine(in)

  Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes

• sn-glycerol 3-phosphateReach 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. sn-glycero-3-phospho-1D-myo-inositol + H2O = myo-inositol + sn-glycerol 3-phosphate + H(+)

  Catalysed by ABHD12, GDE1

• ethanolamineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + L-serine = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + ethanolamine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 moreOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• an N-acylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• guanidinoacetateReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of Guanidinoacetic Acid

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular space

• sphinganineReach 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 morecytosolOne of 2 routes

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

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

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 15 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• L-tryptophanReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Tryptophan by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 12 routes

• L-kynurenineReach 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 L-Kynurenine

  Catalysed by PM20D1, SLC7A8extracellular space, cytosolOne of 4 routes

• beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of beta-alanine and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A6endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. sn-glycerol 3-phosphate + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA

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

• L-alanineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

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

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• L-tyrosineReach 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

• 1D-myo-inositol 1-phosphateReach from here →
  1. 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(+)
  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-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycerol + 1D-myo-inositol 1-phosphate + H(+)

  Catalysed by ABHD16A, GDPD2One of 3 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)Reach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(in) + cholesterol(out)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 5 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• (3Z)-dodecenoyl-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-oxomyrist-5-enoyl-CoA)

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

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 17 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol, extracellular space