hexadecanoic acid

Three steps

• itaconateReach from here →
  1. Fas180
  2. Itaconate:CoA ligase (GDP-forming)
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by SUCLG1, SUCLG2, SUCLA2cytosol, mitochondrial matrixOne of 4 routes

• N-octadecanoyl-heptadecasphing-4-enineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. heptadecasphing-4-enine + octadecanoyl-CoA = N-octadecanoyl-heptadecasphing-4-enine + CoA + H(+)

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

• all-trans-retinolReach from here →
  1. Fas180
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. all-trans-Retinol 11-cis-trans-isomerase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosolOne of 2 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

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

• AH2Reach from here →
  1. Fas180
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)

  Catalysed by BAAT, MTO1cytosolOne of 6 routes

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. Fas180
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Lecithin Retinol Acyltransferase (11-Cis)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosol

• S-methyl-5'-thioadenosineReach from here →
  1. Fas180
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase

  Catalysed by SAT1, SAT2, SRM, SMScytosolOne of 2 routes

• 5-aminolevulinic acidReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by GLYAT, GLYATL2, GLYATL1, ALAS1 and 2 morecytosol, mitochondrial matrixOne of 2 routes

• O-phosphoethanolamineReach from here →
  1. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. Sphinganine-1-phosphate pamlmitaldehyde-lyase

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2, SGPL1cytosol, endoplasmic reticulum

• all-trans-retinyl hexadecanoateReach from here →
  1. Fas180
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosolOne of 2 routes

• Ala-tRNA(Ala)Reach from here →
  1. Fas180
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-Alanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by AARS1cytosol, mitochondrial matrix

• glycine betaineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of betaine and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A12endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• CHEBI:17769Reach from here →
  1. Fas180
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine:(acceptor) oxidoreductase

  Catalysed by SAT1, SAT2cytosol

• a 1,2-diacyl-sn-glycerolReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA

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

• a triacylglycerolReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

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

• CHEBI:17895Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Tyrosine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 21 routes

• butanoateReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ACOT8 and 5 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• CHEBI:18019Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and lysine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 11 routes

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

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 30 routes

• spermine monoaldehydeReach from here →
  1. Fas180
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. primary-amine oxidase (spermine)

  Catalysed by SAT1, SAT2, AOC2, AOC1 and 1 morecytosolOne of 3 routes

• CHEBI:18095Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of trans-4-hydroxy-L-proline (cytosol to extracellular)

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• CHEBI:18132Reach from here →
  1. Fas180
  2. Acetyl-CoA:choline O-acetyltransferase
  3. ATP:choline phosphotransferase

  Catalysed by CHAT, CHKA, CHKBcytosol, nucleus

• N-carbamoyl-beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of 3-Ureidopropionate

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

• N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GARTcytosol, mitochondrial matrix

• N-(4-aminobutyl)-3-aminopropanalReach from here →
  1. Fas180
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. primary-amine oxidase (spermidine)

  Catalysed by SAT1, SAT2, AOC2, AOC1 and 1 morecytosolOne of 3 routes

• superoxideReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-peroxy-docosahexaenoate to DHA conversion

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

• 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. Fas180
  2. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)
  3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by ABHD11cytosol

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + O2 = (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoA + H2O2

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

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

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

• ophthalmateReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GSScytosol, mitochondrial matrix

• S-methylmercury-L-cysteineReach from here →
  1. Fas180
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by NAGS, SLC7A8cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-aminoisobutanoateReach from here →
  1. Fas180
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 11-cis-retinyl esterReach from here →
  1. Fas180
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol + a fatty acyl-CoA = 11-cis-retinyl ester + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosol

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

  Catalysed by ALOX5cytosol, extracellular space

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. Fas180
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by ACLY, AGXT2cytosol

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by GLYAT, GLYATL2, GLYATL1, AGXT2cytosol, mitochondrial matrixOne of 2 routes

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, MOGAT2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

  Catalysed by GLYAT, GLYATL2, GLYATL1, SHMT1cytosol, mitochondrial matrixOne of 2 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, CRATendoplasmic reticulum, cytosol, mitochondrial matrix

• S-disulfanyl-L-cysteineReach from here →
  1. Fas180
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by NAGS, CARS2cytosol, mitochondrial matrix

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by UGT1A9, UGT2B7, UGT1A6, UGT1A1 and 2 morecytosol, extracellular space

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. Fas180
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

  Catalysed by CPT1A, CPT1C, CPT1B, ELOVL7 and 6 morecytosol

• S-hexadecanoyl-N-acetylcysteamineReach from here →
  1. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]
  2. hexadecanoate + NADH + 2 H(+) = hexadecanal + NAD(+) + H2O
  3. S-hexadecanoyl-N-acetylcysteamine + H2O = N-acetylcysteamine + hexadecanoate + H(+)

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2, PPT1 and 1 morecytosol

• S-hexadecanoyl-N-acetylcysteine methyl esterReach from here →
  1. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]
  2. hexadecanoate + NADH + 2 H(+) = hexadecanal + NAD(+) + H2O
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2, PPT1cytosol

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. Fas180
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by HADHA, ACADVL, HADHB, ACADL and 1 morecytosol, mitochondrial matrix

• (2E,4Z,7Z,10Z,13Z)-hexadecapentaenoyl-CoAReach from here →
  1. Fas180
  2. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
  3. Fatty Acid Beta Oxidation (C16:4->C16:5), Mitochondrial

  Catalysed by HADHA, ACADVL, HADHBcytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Fas180
  2. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial
  3. (7Z,10Z,13Z)-hexadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by HADHA, ACADVL, HADHB, ACADL and 1 morecytosol, mitochondrial matrix