CHEBI:15467

Three steps

• sphinga-4E,14Z-dienineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + CoA

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

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

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

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

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

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, endoplasmic reticulum

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

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

• O-octadecanoyl-(R)-carnitineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

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

• O-eicosanoyl-(R)-carnitineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

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

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Carnitine O-Palmitoyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by HMGCR, CPT1A, CPT1C, CPT1B and 2 morecytosol, peroxisomeOne of 7 routes

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

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

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

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

• O-3-oxobutanoyl-(R)-carnitineReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate
  3. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA

  Catalysed by HMGCL, AACS, CRATperoxisome

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, endoplasmic reticulumOne of 2 routes

• N-tetradecanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

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

• N-eicosanoylglycinateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

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

• N-docosanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

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

• N-hexacosanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

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

• an N(2)-acyl-L-glutamineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by HMGCR, ASAH1, ACER2, ACER1 and 3 morecytosol, Golgi apparatus

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

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

• a 3-oxoacyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by HMGCR, ASAH1, ACER2, ACER1 and 5 morecytosol, Golgi apparatus

• taurochenodeoxycholateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by HMGCR, ACAA1, SCP2, MYO5B and 1 morecytosol, peroxisomeOne of 5 routes

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by HMGCL, PDHA1, PDHB, PDHA2peroxisome, mitochondrial matrix, cytosol