CHEBI:15467

Three steps

• 2-hydroxyoctanoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by HMGCR, CROT, PHYHcytosol, mitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by HMGCR, ACSM4, ACSM1, ACSM2A and 4 morecytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

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

• 2-hydroxydodecanoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

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

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

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

• 11-cis-retinyl tetradecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

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

• 9-cis-retinyl tetradecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

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

• 13-cis-retinyl tetradecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

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

• all-trans-retinyl tetradecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

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

• tetradecyl tetradecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

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

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

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

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by HMGCL, SLC16A4, SLC16A5, UGT1A1 and 2 moreperoxisome, extracellular space, cytosol, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by HMGCL, SLC16A4, SLC16A5, CYP1A1 and 24 moreperoxisome, extracellular space, cytosolOne of 2 routes

• a phenyl acetateReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetate and acetoacetate (cytosol to extracellular)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by HMGCL, SLC16A4, SLC16A5, SLC16A6 and 5 moreperoxisome, extracellular space, cytosol

• N-hexadecanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

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

• N-dodecanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

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

• N-decanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by HMGCR, ACSM4, ACSM1, ACSM2A and 4 morecytosolOne of 2 routes

• N-octanoylglycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by HMGCR, CROT, GLYATL2cytosol, mitochondrial matrixOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

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

• L-cystine-bis-glycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1 and 2 morecytosol, mitochondrial matrix

• an N-octadecanoyl-sphingoid baseReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

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

• glycyldehydrophenylalanineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

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

• an N-(fatty acyl)-glycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrix

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

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

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

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

• cholesteryl (7Z)-octadecenoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

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

• acetylcholineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by HMGCR, CHATcytosol, nucleusOne of 3 routes

• acetylpyruvateReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by HMGCL, FAHD1peroxisome, mitochondrial matrix, cytosolOne of 2 routes

• CHEBI:15570Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1 and 2 morecytosol, mitochondrial matrix, extracellular spaceOne of 3 routes

• (S)-malateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. ATP citrate lyase (citrate)
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by HMGCR, ACLYcytosol, mitochondrial matrixOne of 7 routes

• L-leucineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and leucine (cytosol to extracellular)

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 21 routes

• CHEBI:15611Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

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

• 10-formyltetrahydrofolic acidReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and formate (cytosol to extracellular)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by HMGCL, SLC16A4, SLC16A5, MTHFD1peroxisome, extracellular space, cytosolOne of 2 routes

• CHEBI:15699Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and homoserine (cytosol to extracellular)

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 17 routes

• betaine aldehydeReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Acetyl-CoA:choline O-acetyltransferase
  3. choline dehydrogenase (choline)

  Catalysed by HMGCR, CHAT, CHDHcytosol, nucleusOne of 3 routes

• trimethylenediamineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. deoxyhypusine synthase (1,3-diaminopropane)

  Catalysed by HMGCR, SAT1, SAT2, DHPScytosolOne of 2 routes

• hexadecanoic acidReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

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

• (R)-2-hydroxyglutarateReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. (S)-3-hydroxybutanoate + 2-oxoglutarate = (R)-2-hydroxyglutarate + acetoacetate
  3. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]

  Catalysed by HMGCL, ADHFE1peroxisome, mitochondrial matrixOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• CHEBI:15971Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and histidine (cytosol to extracellular)

  Catalysed by HMGCR, GLYAT, GLYATL2, GLYATL1 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 11 routes

• phosphatidylethanolamineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

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

• 11-cis-retinalReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol:NAD+ oxidoreductase

  Catalysed by HMGCR, DGAT1, LRAT, AWAT1 and 9 morecytosolOne of 4 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• hexadecan-1-olReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Palmitate:CoA ligase (AMP-forming)
  3. formate dehydrogenase (palmitoyl-CoA)

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, peroxisome

• 11-cis-retinyl hexadecanoateReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by HMGCR, SLC27A2, ACSL4, ACSL3 and 10 morecytosolOne of 3 routes

• 2-methyl-3-oxopropanoic acidReach from here →
  1. hydroxymethylglutaryl-CoA lyase
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by HMGCL, AGXT2peroxisome, mitochondrial matrix, cytosol

• L-cystineReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of L-Cystine (L-Alanine antiport) by B0, +At Transporter

  Catalysed by HMGCR, SLC7A9, SLC3A1cytosol, mitochondrial matrix, extracellular spaceOne of 5 routes

• (R)-3-aminoisobutyric acidReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by HMGCR, AGXT2cytosol, mitochondrial matrix

• phosphatidic acidReach from here →
  1. (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by HMGCR, ASAH1, ACER2, ACER1 and 10 morecytosol, Golgi apparatus, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. Formation of 3-Hydroxy-3-Methyl-Glutarate
  2. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate
  3. glutarate(in) + (R)-carnitine(out) = glutarate(out) + (R)-carnitine(in)

  Catalysed by SUGCT, SLC22A8cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes