O-eicosanoyl-(R)-carnitine

Three steps

• (R)-methylmalonyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 1 morecytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by CPT2, BAAT, ACOT6, ACOT1cytosol, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 1 morecytosol, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by CPT2, BAAT, ACOT6, ACOT1cytosol, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 2 morecytosol, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 8 routes

• butanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 6 morecytosolOne of 9 routes

• dodecanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. dodecanoyl-CoA + (R)-carnitine = O-dodecanoyl-R-carnitine + CoA
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by CPT2, CPT1A, CPT1C, CPT1BcytosolOne of 14 routes

• glutaryl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. glutarate + succinyl-CoA = glutaryl-CoA + succinate

  Catalysed by CPT2, SLC22A8, SUGCTinner side of the membrane, outer side of the membraneOne of 6 routes

• hexadecanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. (R)-carnitine + hexadecanoyl-CoA = O-hexadecanoyl-(R)-carnitine + CoA
  3. (R)-carnitine + hexadecanoyl-CoA = O-hexadecanoyl-(R)-carnitine + CoA

  Catalysed by CPT2, CPT1A, CPT1B

• itaconyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 3 morecytosol, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 14 routes

• tetradecanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by CPT2One of 13 routes

• octanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. octanoyl-CoA + (R)-carnitine = O-octanoyl-(R)-carnitine + CoA
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by CPT2, CRAT, CROTmitochondrial matrixOne of 23 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA
  3. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

  Catalysed by CPT2One of 2 routes

• phytanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. phytanate-CoA ligase

  Catalysed by CPT2, BAAT, ACOT6, ACOT1cytosolOne of 5 routes

• prostaglandin F2alphaReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. prostaglandin F2alpha(out) + glutarate(in) = prostaglandin F2alpha(in) + glutarate(out)

  Catalysed by CPT2, SLC22A8inner side of the membrane, outer side of the membraneOne of 2 routes

• a 1-acylglycerone 3-phosphateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by CPT2, GNPATcytosol

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CPT2, LPGAT1cytosolOne of 2 routes

• an N-acylglycineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by CPT2, GLYATL3, GLYAT, GLYATL2cytosol

• sphing-4-enineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 4 morecytosol, Golgi apparatusOne of 3 routes

• spermidineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 2 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glycine betaine(out) + (R)-carnitine(in) = glycine betaine(in) + (R)-carnitine(out)
  3. Trimethylaminoacetate:L-homosysteine S-methyltransferase

  Catalysed by CPT2, SLC22A5, BHMT, BHMT2inner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, LCLAT1, MBOAT7cytosol

• dehydroepiandrosterone 3-sulfateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. dehydroepiandrosterone 3-sulfate(out) + glutarate(in) = dehydroepiandrosterone 3-sulfate(in) + glutarate(out)

  Catalysed by CPT2, SLC22A8, SLC22A24inner side of the membrane, outer side of the membraneOne of 2 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, GPAT3, GPAT2, GPAT4 and 1 morecytosol

• L-alanineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1cytosol, mitochondrial matrix

• L-asparagineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 1 morecytosol, mitochondrial matrix

• L,L-cystathionineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 1 morecytosol, mitochondrial matrix

• N,N-dimethylglycineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glycine betaine(out) + (R)-carnitine(in) = glycine betaine(in) + (R)-carnitine(out)
  3. L-homocysteine + glycine betaine = N,N-dimethylglycine + L-methionine

  Catalysed by CPT2, SLC22A5, BHMTinner side of the membrane, outer side of the membrane

• kynurenateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. kynurenate(out) + glutarate(in) = kynurenate(in) + glutarate(out)

  Catalysed by CPT2, SLC22A8, SLC22A6inner side of the membrane, outer side of the membraneOne of 2 routes

• (3Z)-dodecenoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 3 morecytosol, mitochondrial matrixOne of 3 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, AGPAT2, GPAT3, GPAT2 and 10 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 2 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 2 morecytosolOne of 4 routes

• estrone 3-sulfateReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. estrone 3-sulfate(out) + glutarate(in) = estrone 3-sulfate(in) + glutarate(out)

  Catalysed by CPT2, SLC22A8, SLC22A24, SLC22A11inner side of the membrane, outer side of the membraneOne of 2 routes

• prostaglandin E2Reach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. prostaglandin E2(out) + glutarate(in) = prostaglandin E2(in) + glutarate(out)

  Catalysed by CPT2, SLC22A8inner side of the membrane, outer side of the membraneOne of 2 routes

• decanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 6 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 3 morecytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 12 routes

• a cardiolipinReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, HADHAcytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 2 morecytosol

• an all-trans-retinyl esterReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by CPT2, DGAT1, PNPLA4, AWAT2 and 1 morecytosol

• CHEBI:63544Reach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 8 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, LPCAT4, LPCAT3, MBOAT1 and 1 morecytosol

• a triacyl-sn-glycerolReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by CPT2, DGAT1, MOGAT2, AWAT2 and 3 morecytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  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 CPT2, LCLAT1, LPCAT1, GPAMcytosol

• hexacosanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 6 routes

• tetracosanoyl-CoAReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by CPT2, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 11 routes

• 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA
  2. Beta Oxidation of Long Chain Fatty Acid
  3. a 2-acyl-sn-glycero-3-phospho-D-myo-inositol + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by CPT2, ACADM, ACADS, LCLAT1mitochondrial matrix