decanoyl-CoA

Three steps

• citric acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. ATP citrate lyase (citrate)
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by ACLY, CScytosol, mitochondrial matrixOne of 2 routes

• butyric acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Butanoate:CoA ligase (AMP-forming)
  3. Butyryl-CoA hydrolase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 morecytosol

• tetradecanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. Myristoyl-CoA hydrolase

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

• (9Z)-octadecenoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 3 routes

• adipic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Activation of adipic acid for Formation of Adipoyl Carnitine
  3. Thioesterification of adipoyl-CoA for Release into Cytosol

  Catalysed by ACOT8cytosol, peroxisomeOne of 3 routes

• glutarateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Production of Glutaryl Carnitine
  3. glutaryl-CoA + H2O = glutarate + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ACOT8 and 1 morecytosolOne of 5 routes

• 4-hydroxy-2-oxoglutaric acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. ATP citrate lyase (citrate)
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by ACLY, GOT2cytosol, mitochondrial matrix

• docosan-1-olReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + 2 NADPH + 2 H(+) = docosan-1-ol + 2 NADP(+) + CoA

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

• hexacosanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. Hexacosanoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

• tetracosanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. Tetracosenoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 4 routes

• an N-acylsphinganineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphingosine N-acyltransferase (sphinganine)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 6 morecytosol, Golgi apparatus

• octadecan-1-olReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 NADPH + 2 H(+) = octadecan-1-ol + 2 NADP(+) + CoA

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

• eicosanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. Eicosanoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• (9Z)-hexadecenoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 8 routes

• (15Z)-tetracosenoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (nervonic acid)
  3. (15Z)-tetracosenoyl-CoA hydrolase

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

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 4 routes

• (11Z)-eicosenoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)
  3. (11Z)-eicosenoyl-CoA hydrolase

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

• putrescineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)

  Catalysed by SAT1, SAT2, SRMcytosolOne of 3 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by NAGS, IL4I1cytosol, mitochondrial matrix

• di-mu-sulfido-diiron(2+)Reach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. De novo synthesis of 2Fe2S

  Catalysed by NAGS, NDUFAB1, FDXR, FXN and 4 morecytosol, mitochondrial matrix

• D-cysteineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

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

• D-serineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)

  Catalysed by SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 6 routes

• an acylcholineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Acetyl-CoA:choline O-acetyltransferase
  3. an acylcholine + H2O = a carboxylate + choline + H(+)

  Catalysed by CHAT, BCHEcytosol, nucleus

• fatty acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase (elaidate)
  3. (10Z)-heptadecenoic acid formation

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

• 5-aminolevulinateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA + glycine + H(+) = 5-aminolevulinate + CO2 + CoA

  Catalysed by GLYAT, GLYATL2, GLYATL1, ALAS1 and 1 morecytosol, mitochondrial matrix

• 12-hydroxydodecanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Lauroyl-CoA hydrolase
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by ACOT7, BAAT, ACOT1, ACOT13 and 2 morecytosolOne of 2 routes

• chenodeoxycholateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. chenodeoxycholoyl-CoA hydrolase

  Catalysed by ACAA1, SCP2, MYO5B, ACOT7 and 2 morecytosol, peroxisomeOne of 3 routes

• glycochenodeoxycholateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)

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

• taurocholateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. propanoyl-CoA C-acyltransferase
  3. Choloyl-CoA:glycine N-choloyltransferase

  Catalysed by ACAA1, SCP2, MYO5B, BAATcytosol, peroxisomeOne of 5 routes

• taurodeoxycholateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, SLC27A5, BAATcytosolOne of 4 routes

• glycochenodeoxycholic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by ACAA1, SCP2, MYO5B, BAATcytosol, peroxisomeOne of 5 routes

• cholesteryl hexadecanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Palmitate:CoA ligase (AMP-forming)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

• glyoxylateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine + 2-oxoglutarate = glyoxylate + L-glutamate

  Catalysed by GLYAT, GLYATL2, GLYATL1, AADATcytosol, mitochondrial matrixOne of 12 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 morecytosol, Golgi apparatus

• CHEBI:36882Reach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA hydro-lyase (itaconyl-CoA-forming)

  Catalysed by SUCLG1, SUCLG2, SUCLA2, AUHcytosol, mitochondrial matrix

• 3-hydroxyisovaleric acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)
  3. Formation of 3-Hydroxy-Isovalerate

  Catalysed by CPT1A, CPT1Bcytosol, mitochondrial matrix

• 3,7,11,15-tetramethylhexadecanoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. phytanate-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by ACOT2cytosol, peroxisomeOne of 3 routes

• sphingosine 1-phosphateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol, Golgi apparatusOne of 2 routes

• glycolithocholic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. bile acid-CoA:amino acid N-acyltransferase (glycine)

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

• decanamideReach from here →
  1. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  2. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate

  Catalysed by GLYATL2, PAM

• L-2-amino-3-oxobutanoic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Acetyl-CoA:glycine C-acetyltransferase

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

• cholesteryl (9Z,12Z)-octadecadienoateReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, endoplasmic reticulumOne of 2 routes

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Production of Glutaryl Carnitine
  3. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate

  Catalysed by CPT1A, CPT1C, CPT1B, SUGCTcytosol

• phosphoenolpyruvic acidReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. ATP citrate lyase (citrate)
  3. GTP:oxaloacetate carboxy-lyase (adding GTP

  Catalysed by ACLY, PCK1cytosolOne of 2 routes

• 13-cis-retinolReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 13-cis-retinol

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol

• spermineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + spermidine = spermine + S-methyl-5'-thioadenosine + H(+)

  Catalysed by SAT1, SAT2, SMScytosolOne of 2 routes

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, SOAT2 and 1 morecytosol, endoplasmic reticulum

• L-ornithineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by BAAT, GATMcytosolOne of 15 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol, Golgi apparatusOne of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. fatty-acyl-CoA synthase (N-C12:0CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 morecytosol, Golgi apparatus