O-octadecanoyl-(R)-carnitine

Three steps

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
  3. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CPT2, GPAT3, GPAT2, GPAT4 and 2 morecytosol

• 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphateReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
  3. 1-octadecanoyl-sn-glycero-3-phosphate + (9Z,12Z)-octadecadienoyl-CoA = 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CPT2, GPAT3, GPAT2, GPAT4 and 2 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  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 CPT2, ACOT7, BAAT, THEM4 and 3 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
  3. 1-octadecanoyl-sn-glycero-3-phosphate + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CPT2, GPAT3, GPAT2, GPAT4 and 2 morecytosol

• pristanoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. fatty-acid-CoA ligase

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 3 morecytosolOne of 2 routes

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

  Catalysed by CPT2, MOGAT1cytosolOne of 2 routes

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

  Catalysed by CPT2, LPCAT2, LPCAT1cytosol

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CPT2, LPCAT4cytosol

• 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CPT2, SCD, SCD5, LPCAT4 and 2 more

• 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CPT2, SCD, SCD5, MBOAT2

• undecanoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 8 morecytosolOne of 3 routes

• (2E,9Z)-octadecadienoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. medium-chain acyl-CoA dehydrogenase (oleoyl-CoA)

  Catalysed by CPT2, SCD, ACADM, ACADL and 2 morecytosol, mitochondrial matrixOne of 4 routes

• N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = 2-octadecanoyl-sn-glycero-3-phosphocholine + N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)

  Catalysed by CPT2, LPCAT3, PLA2G4E

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + L-serine = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + ethanolamine

  Catalysed by CPT2, LPGAT1, PTDSS2

• 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-(1Z-octadecenyl)-sn-glycero-3-phosphoethanolamine + 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine = 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + 1-octadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CPT2, LPGAT1, TMEM164

• hexadecanoateReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + H2O = 2-octadecanoyl-sn-glycero-3-phosphocholine + hexadecanoate + H(+)

  Catalysed by CPT2, LPCAT3, PLAAT3

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

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

• 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z)-octadecenoyl-CoA = 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by CPT2, SCD, SCD5, HADHA

• (5Z)-tetradecenoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 10 morecytosolOne of 9 routes

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by CPT2, CERS1, TLCD3B, CERS2 and 2 more

• (3E)-decenoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 6 morecytosol, mitochondrial matrix

• 1-decanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CPT2, SCD, SCD5, MOGAT2

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 5 morecytosol, mitochondrial matrix

• an N(2)-acyl-L-glutamineReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by CPT2, GLYATL1B, GLYATL1cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 10 morecytosolOne of 10 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by CPT2, SCD, SOAT1cytosol

• tricosanoyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by CPT2, ACOT7, BAAT, THEM4 and 10 morecytosolOne of 5 routes

• a 3-oxoacyl-CoAReach from here →
  1. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by CPT2, ACAA1, SCP2, ACAA2 and 1 morecytosol