1-acyl-sn-glycerol 3-phosphate

Three steps

• an acyl-4'-phosphopantetheineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + H2O = an acyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 12 moremitochondrial matrix, Golgi apparatus

• tauroursodeoxycholateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine to tauroursodeoxycholate conversion

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrix, cytosolOne of 2 routes

• glycoursodeoxycholateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine to glycoursodeoxycholate conversion

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrix, cytosolOne of 2 routes

• leukotriene F4Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. leukotriene F4 hydrolysis

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 36 moremitochondrial matrix, cytosol

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 37 moremitochondrial matrix, cytosol, extracellular spaceOne of 2 routes

• N-(9Z-octadecenoyl)glycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix

• N-octadecanoylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 moremitochondrial matrix, cytosolOne of 2 routes

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosolOne of 2 routes

• 2-hydroxyoctanoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 12 moremitochondrial matrix, cytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• 11-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosolOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• 13-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• tetradecyl tetradecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  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 AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 moremitochondrial matrix, cytosol

• N-hexadecanoylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix

• N-dodecanoylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosolOne of 2 routes

• N-decanoylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 12 moremitochondrial matrix, cytosolOne of 2 routes

• N-octanoylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrixOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  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 AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix

• L-cystine-bis-glycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 10 moremitochondrial matrix

• an N-octadecanoyl-sphingoid baseReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 moremitochondrial matrix, cytosol

• glycyldehydrophenylalanineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix

• an N-(fatty acyl)-glycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrix

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  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 AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosol

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  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 AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, cytosolOne of 2 routes

• cholesteryl (7Z)-octadecenoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, cytosol

• acetylcholineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrix, nucleus, cytosolOne of 3 routes

• pyruvateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrixOne of 20 routes

• CHEBI:15467Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Acetoacetate:CoA ligase (AMP-forming)
  3. 3-hydroxy-3-methylglutaryl-CoA synthase (acetoacetyl-CoA)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, cytosolOne of 3 routes

• CHEBI:15570Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 10 moremitochondrial matrix, extracellular space, cytosolOne of 3 routes

• (S)-malateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. ATP citrate lyase (citrate)
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrix, cytosolOne of 5 routes

• L-leucineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and leucine (cytosol to extracellular)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, extracellular space, cytosolOne of 21 routes

• CHEBI:15611Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, cytosol

• CHEBI:15699Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and homoserine (cytosol to extracellular)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, extracellular space, cytosolOne of 17 routes

• betaine aldehydeReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. choline dehydrogenase (choline)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, nucleus, cytosolOne of 3 routes

• trimethylenediamineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. deoxyhypusine synthase (1,3-diaminopropane)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrix, cytosolOne of 2 routes

• hexadecanoic acidReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Utilized Transport

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 17 routes

• CHEBI:15971Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and histidine (cytosol to extracellular)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, extracellular space, cytosolOne of 11 routes

• phosphatidylethanolamineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 14 moremitochondrial matrix, Golgi apparatus, cytosolOne of 2 routes

• 11-cis-retinalReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol:NAD+ oxidoreductase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 17 moremitochondrial matrix, cytosolOne of 4 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 moremitochondrial matrix, Golgi apparatus, cytosolOne of 2 routes

• hexadecan-1-olReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. formate dehydrogenase (palmitoyl-CoA)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 15 moremitochondrial matrix, cytosol, peroxisome

• 11-cis-retinyl hexadecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 18 moremitochondrial matrix, cytosolOne of 3 routes

• L-cystineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of L-Cystine (L-Alanine antiport) by B0, +At Transporter

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, extracellular space, cytosolOne of 5 routes

• (R)-3-aminoisobutyric acidReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrix