oleoyl-CoA

Three steps

• S-methyl-5'-thioadenosineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 3 morecytosolOne of 2 routes

• 5-aminolevulinic acidReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 5 morecytosol, mitochondrial matrixOne of 2 routes

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

  Catalysed by CPT1A, CPT1C, CPT1B, DGAT1 and 5 morecytosol

• a sphingomyelinReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 2 morecytosol, Golgi apparatusOne of 5 routes

• 26-hydroxycholesterolReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SOAT2, SOAT1, CEL, CES1 and 4 moreendoplasmic reticulum

• Ala-tRNA(Ala)Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-Alanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by CPT1A, CPT1C, CPT1B, AARS1cytosol, mitochondrial matrix

• desmosterolReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. 3-hydroxyacyl-CoA dehydrogenase (desmosterol)

  Catalysed by SOAT2, SOAT1, CEL, LIPAendoplasmic reticulum, lysosome, nucleus

• glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA
  3. a 1-acylglycerol + a 1,2-diacylglycerol = a triacylglycerol + glycerol

  Catalysed by MOGAT2, MOGAT3, LPGAT1, TMEM68 and 4 morecytosolOne of 2 routes

• CHEBI:17769Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine:(acceptor) oxidoreductase

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 1 morecytosol

• CHEBI:17895Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and tyrosine (cytosol to extracellular)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 19 routes

• butanoateReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 11 morecytosol

• 4-methylpentanalReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. cytochrome P450 (cholesterol)

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 1 moreendoplasmic reticulum, lysosome, mitochondrial matrixOne of 2 routes

• CHEBI:18019Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and lysine (cytosol to extracellular)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 10 routes

• a diacylglycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase
  3. a triacylglycerol + H2O = a diacylglycerol + a fatty acid + H(+)

  Catalysed by DGAT1, MOGAT2, MOGAT3, MOGAT1 and 20 morecytosolOne of 2 routes

• L-glutamineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glutamine and glycine (cytosol to extracellular)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 30 routes

• spermine monoaldehydeReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. primary-amine oxidase (spermine)

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 4 morecytosolOne of 3 routes

• CHEBI:18095Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of Hydroxy-Proline

  Catalysed by CPT1A, CPT1C, CPT1B, SLC1A4cytosol, mitochondrial matrix, extracellular space

• CHEBI:18132Reach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. Acetyl-CoA:choline O-acetyltransferase
  3. ATP:choline phosphotransferase

  Catalysed by CPT1A, CPT1C, CPT1B, CHAT and 2 morecytosol, nucleus

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

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 11 morecytosolOne of 14 routes

• phosphatidyl-L-serineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. phosphatidylserine synthase (PC-LD pool)

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 1 morecytosolOne of 2 routes

• N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

• N-(4-aminobutyl)-3-aminopropanalReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. primary-amine oxidase (spermidine)

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 4 morecytosolOne of 3 routes

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  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 CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• cholesteryl 3-beta-D-galactosideReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  3. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine

  Catalysed by SOAT2, SOAT1, CEL, CES1 and 5 moreendoplasmic reticulumOne of 2 routes

• cholesteryl 3-beta-D-xylosideReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  3. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by SOAT2, SOAT1, CEL, CES1 and 5 moreendoplasmic reticulumOne of 2 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. Oleoyl-CoA hydrolase
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-sphing-4-enine + UDP-alpha-D-xylose = beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enine + UDP + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 7 morecytosol

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosol

• ophthalmateReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

• S-methylmercury-L-cysteineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  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 CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-aminoisobutanoateReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 11-cis-retinyl esterReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol + a fatty acyl-CoA = 11-cis-retinyl ester + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, DGAT1 and 4 morecytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by CPT1A, CPT1C, CPT1B, ACLY and 1 morecytosol

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 7 morecytosol

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

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 9 morecytosol

• 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 3-octadecanoyl-sn-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol

• 1-octanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol

• 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-dodecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 11 morecytosol

• 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 11 morecytosol

• 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 11 morecytosol

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol

• 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-tetradecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol

• 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-(9Z-octadecenyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 15 morecytosol

• 1-decanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Oleoyl-CoA hydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 6 morecytosol

• S-disulfanyl-L-cysteineReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrix

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. Oleoyl-CoA hydrolase
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 2 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) = 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  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

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  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 CPT1A, CPT1C, CPT1B, SLC27A2 and 10 morecytosolOne of 2 routes