(9Z)-hexadecenoate

Three steps

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

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular space

• sphing-4-enineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, Golgi apparatusOne of 2 routes

• 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 morecytosol

• spermidineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  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 2 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 (palmitolate)
  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 (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

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

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

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

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• 3-oxosphinganineReach 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. L-serine + hexadecanoyl-CoA + H(+) = 3-oxosphinganine + CO2 + CoA

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

• 1-hexadecanoylglycerone 3-phosphateReach 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. dihydroxyacetone phosphate + hexadecanoyl-CoA = 1-hexadecanoylglycerone 3-phosphate + CoA

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

• (3Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

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

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  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 (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 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

• 4-aminobutanoateReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A12endoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  No catalyst recordedcytosol, extracellular space

• decanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 15 morecytosolOne of 8 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

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

• (2E)-octenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Beta Oxidation Fatty Acid
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 5 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• an all-trans-retinyl esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

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

• CHEBI:63544Reach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 10 routes

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CYP4F8cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

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

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

• a triacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

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

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

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

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach 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-(9Z-octadecenoyl)-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

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

• 1-acyl-2-hexadecanoyl-sn-glycero-3-phosphateReach 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-acyl-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate + CoA

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

• hexacosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

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

• tetracosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 17 routes

• docosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 14 routes

• N-hexadecanoyl-(4R)-hydroxysphinganineReach 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. (4R)-hydroxysphinganine + hexadecanoyl-CoA = N-hexadecanoyl-(4R)-hydroxysphinganine + CoA + H(+)

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

• N-hexadecanoylsphinganineReach 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. sphinganine + hexadecanoyl-CoA = N-hexadecanoylsphinganine + CoA + H(+)

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

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

• 3-oxooctadecanoyl-CoAReach 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 + malonyl-CoA + H(+) = 3-oxooctadecanoyl-CoA + CO2 + CoA

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

• (2E)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (palmitolate)
  2. Palmitoleoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

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

• 1-O-hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach 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-O-hexadecyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-O-hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA

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

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD12cytosol, extracellular space

• 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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

• 1-tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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-tetradecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1-tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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

• 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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

• 1-(9Z-octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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-(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 SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach 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-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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