1-acylglycerone 3-phosphate

Three steps

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by AGPS, ASAH1, ACER2, ACER1 and 4 moreperoxisome, cytosol

• (2E)-octadecenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 8 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by AGPS, ABHD12peroxisome, extracellular space

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

  Catalysed by AGPS, ABHD16Aperoxisome, extracellular space

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, AGPAT2cytosol

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, AGPAT2cytosol

• 1,2-dihexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, AGPAT2cytosol

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, AGPAT2, AGPAT3cytosol

• N-dodecanoylsphing-4-enineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine

  Catalysed by AGPS, NAAA, ASAH1, ACER2 and 1 moreperoxisome, extracellular space

• N-tetradecanoylsphing-4-enineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

  Catalysed by AGPS, ASAH1, ACER2, ASAH2peroxisome, extracellular space

• N-octadecanoylsphing-4-enineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate

  Catalysed by AGPS, ASAH1, ACER2, ASAH2peroxisome, extracellular space

• (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoAReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z)-docosatetraenoate + ATP + CoA = (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by AGPS, ACSL4peroxisome, extracellular space

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 8 routes

• 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, MBOAT2cytosol

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 9 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 6 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 9 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 5 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 4 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 8 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 6 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 7 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 5 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 10 routes

• heptadecanoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 5 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 5 routes

• N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine

  Catalysed by AGPS, ACER2, ACER1, ASAH2peroxisome, extracellular space

• 1-(9Z,12Z)-octadecadienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z)-octadecadienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, LCLAT1cytosol

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-octadecanoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, LPCAT2, ABHD5, AGPAT3 and 1 morecytosol

• 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-tetradecanoyl-sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, AGPAT2, GPAT3, AGPAT1cytosol

• 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by AKR1A1, GPAT3, ABHD5, AGPAT5cytosol

• nonadecanoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 14 morecytosol, mitochondrial matrixOne of 6 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by AGPS, ALOX12Bperoxisome, extracellular space

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by AGPS, ALOX12peroxisome, extracellular space, cytosolOne of 2 routes

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by AGPS, ABHD11peroxisome, extracellular space

• 1-tetradecanoyl-sn-glycerolReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-tetradecanoyl-sn-glycerol 3-phosphate + H2O = 1-tetradecanoyl-sn-glycerol + phosphate

  Catalysed by AKR1A1, EPHX2cytosol

• 1-hexadecanoyl-sn-glycerolReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + H2O = 1-hexadecanoyl-sn-glycerol + phosphate

  Catalysed by AKR1A1, EPHX2cytosol

• 1-octadecanoyl-sn-glycerolReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 1-octadecanoyl-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycerol + phosphate

  Catalysed by AKR1A1, EPHX2cytosol

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by AGPS, FAAHperoxisome, extracellular space, cytosol

• (R)-2-hydroxytetracosanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. tetracosanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxytetracosanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by AGPS, FA2Hperoxisome, extracellular space

• a 1-O-alkyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. a 1-O-alkylglycerone 3-phosphate + NADPH + H(+) = a 1-O-alkyl-sn-glycero-3-phosphate + NADP(+)
  3. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)

  Catalysed by AGPS, DHRS7B, ENPP2peroxisome

• docosanedioateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation by Hydroxylases (C22->C22Dc), Endoplasmatic Reticulum

  Catalysed by AGPS, CYP4F2, CYP4F3peroxisome, extracellular space, endoplasmic reticulum

• dodecanedioyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Activation of dodecanedioic acid

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 6 morecytosol, mitochondrial matrixOne of 4 routes

• decanedioyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Production of Sebacoylcarnitine

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• octanedioyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Production of Suberylcarnitine

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 6 morecytosol, mitochondrial matrixOne of 4 routes