1-acyl-sn-glycerol 3-phosphate

Three steps

• N-(4-aminobutyl)-3-aminopropanalReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. primary-amine oxidase (spermidine)

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

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + O2 = (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoA + H2O2

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

• 1-octadecanoyl-2-acyl-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 (stearate)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

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

• ophthalmateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

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

• S-methylmercury-L-cysteineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-aminoisobutanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 11-cis-retinyl esterReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol + a fatty acyl-CoA = 11-cis-retinyl ester + CoA

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

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

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

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrixOne of 2 routes

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach 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-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, cytosolOne of 2 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

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

• S-disulfanyl-L-cysteineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

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

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

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

• S-hexadecanoyl-N-acetylcysteamineReach from here →
  1. 1-acylglycerol-3-phosphate pool formation and breakdown
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + H2O = sn-glycerol 3-phosphate + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteamine + H2O = N-acetylcysteamine + hexadecanoate + H(+)

  Catalysed by LYPLA2, PNPLA7, PNPLA6, PPT1 and 1 morecytosol

• S-hexadecanoyl-N-acetylcysteine methyl esterReach from here →
  1. 1-acylglycerol-3-phosphate pool formation and breakdown
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + H2O = sn-glycerol 3-phosphate + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by LYPLA2, PNPLA7, PNPLA6, PPT1cytosol

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 16 moremitochondrial matrix, cytosolOne of 2 routes

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (2E,4Z,7Z,10Z,13Z)-hexadecapentaenoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
  3. Fatty Acid Beta Oxidation (C16:4->C16:5), Mitochondrial

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrixOne of 4 routes

• (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial
  3. (7Z,10Z,13Z)-hexadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (2E,4Z,7Z)-decatrienoyl-CoAReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial
  3. Fatty Acid Beta Oxidation (C10:2->C10:3), Mitochondrial

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrixOne of 3 routes

• docosanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. Docosanoyl-CoA hydrolase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 15 moremitochondrial matrix, cytosolOne of 16 routes

• CHEBI:240943Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• a quinolReach from here →
  1. 1-acylglycerol-3-phosphate pool formation and breakdown
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + H2O = sn-glycerol 3-phosphate + hexadecanoate + H(+)
  3. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol

  Catalysed by LYPLA2, PNPLA7, PNPLA6, GPD2cytosol

• octadecanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Stearoyl-CoA hydrolase

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

• octanoateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. Octanoyl-CoA hydrolase

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

• alpha-linolenic 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 14 routes

• phenylacetylglycineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 moremitochondrial matrix, cytosolOne of 6 routes

• decanoateReach 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 hydrolase

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

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach 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 hydrolase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 15 moremitochondrial matrix, cytosolOne of 14 routes

• hexacosan-1-olReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + 2 NADPH + 2 H(+) = hexacosan-1-ol + 2 NADP(+) + CoA

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

• CHEBI:28666Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. LTD4 hydrolysis

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 36 moremitochondrial matrix, cytosolOne of 2 routes

• O-decanoyl-(R)-carnitineReach 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 + (R)-carnitine = O-decanoyl-(R)-carnitine + CoA

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

• pyridoxine 5'-phosphateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

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

• a fatty acidReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Diacylglycerol Phosphate Kinase (Homo Sapiens)
  3. a 1,2-diacyl-sn-glycerol + H2O = a 2-acylglycerol + a fatty acid + H(+)

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

• N-acetyl-L-cysteineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

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

• K(+)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• Cys-tRNA(Cys)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

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

• Gly-tRNA(Gly)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine:tRNA(Gly) ligase (AMP-forming)

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

• Asn-tRNA(Asn)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-asparagine)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

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

• chlorine(.)Reach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Carnitine Transport by Atb0

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, cytosol, extracellular spaceOne of 15 routes

• phosphocholineReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. phosphocholine + H2O = choline + phosphate

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

• glycocholateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. propanoyl-CoA C-acyltransferase
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, peroxisomeOne of 5 routes

• cholateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. propanoyl-CoA C-acyltransferase
  3. choloyl-CoA hydrolase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 moremitochondrial matrix, peroxisome, cytosolOne of 2 routes

• hydrogen sulfideReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

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

• L-aspartateReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. oxaloacetate + L-alanine = L-aspartate + pyruvate

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 6 moremitochondrial matrixOne of 12 routes

• (9Z,12Z)-octadecadienoateReach 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 + H2O = (9Z,12Z)-octadecadienoate + CoA + H(+)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 17 moremitochondrial matrix, cytosol

• 3-acetamidopropanalReach from here →
  1. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1-acetylspermine:oxygen oxidoreductase (3-acetamidopropanal-forming)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 7 moremitochondrial matrix, cytosolOne of 4 routes