(9Z)-hexadecenoate

Three steps

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular space

• 2-hydroxyoctanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Beta Oxidation Fatty Acid
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

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

• 13-cis-retinyl hexadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 13-cis-retinol + hexadecanoyl-CoA = 13-cis-retinyl hexadecanoate + CoA

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

• 9-cis-retinyl hexadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 9-cis-retinol + hexadecanoyl-CoA = 9-cis-retinyl hexadecanoate + CoA

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

• N-hexadecanoylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

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

• N-octanoylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Beta Oxidation Fatty Acid
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

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

• an N-hexadecanoyl-sphingoid baseReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a sphingoid base + hexadecanoyl-CoA = an N-hexadecanoyl-sphingoid base + CoA + H(+)

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

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)

  Catalysed by DAGLBcytosol, extracellular space

• N-hexadecanoyl-sphinga-4E,14Z-dienineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. sphinga-4E,14Z-dienine + hexadecanoyl-CoA = N-hexadecanoyl-sphinga-4E,14Z-dienine + CoA + H(+)

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

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

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• (7Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 4 routes

• CHEBI:15345Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. Acetoacetate:CoA ligase (AMP-forming)

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

• cholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. Acetyl-CoA:choline O-acetyltransferase

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

• CHEBI:15380Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• 2-methylcrotonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. glycine N-acyltransferase (isovalerylglycine)

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

• arachidonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 15 routes

• CHEBI:15519Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase

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

• oleoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  2. Palmitoleoyl-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

• a 1-hexadecanoyl-2-acylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 2-acylglycerol + hexadecanoyl-CoA = a 1-hexadecanoyl-2-acylglycerol + CoA

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

• an hexadecanoyl-acylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-acylglycerol + hexadecanoyl-CoA = an hexadecanoyl-acylglycerol + CoA

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

• 1-(10Z-heptadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-(10Z-heptadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

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

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

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

• CHEBI:15727Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  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 (palmitolate)
  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 (palmitolate)
  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

• hexadecan-1-olReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. hexadecanoyl-CoA + 2 NADPH + 2 H(+) = hexadecan-1-ol + 2 NADP(+) + CoA

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

• 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. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 11-cis-retinol + hexadecanoyl-CoA = 11-cis-retinyl hexadecanoate + CoA

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

• 11-cis-retinolReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-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 (palmitolate)
  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 (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. ATP citrate lyase (citrate)

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