1-acylglycerone 3-phosphate

Three steps

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by AGPS, ALOX15peroxisome, extracellular space

• 12(S)-HPETEReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by AGPS, ALOX12peroxisome, extracellular space, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by AGPS, ALOX15B, ALOX15peroxisome, extracellular space, cytosolOne of 4 routes

• 5(S)-HPETEReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by AGPS, ALOX5peroxisome, extracellular space, cytosol

• CHEBI:15650Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 37 morecytosol, mitochondrial matrixOne of 2 routes

• CHEBI:15727Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 7 morecytosol, mitochondrial matrix

• CHEBI:15746Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 8 morecytosol, mitochondrial matrixOne of 2 routes

• 11-cis-retinyl hexadecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 11-peroxy-docosahexaenoate to DHA conversion

  Catalysed by AGPSperoxisome, extracellular space, cytosolOne of 3 routes

• 11-cis-retinolReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 11 morecytosol, mitochondrial matrix

• oxaloacetateReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. ATP citrate lyase (citrate)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 7 morecytosol, mitochondrial matrix

• CHEBI:16566Reach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by AGPS, ASAH1, ACER2, ACER1 and 2 moreperoxisome, cytosol

• 8-hydroxydodecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 10-hydroxydodecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 9-hydroxytetradecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 10-hydroxytetradecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 12-hydroxytetradecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• 11-hydroxytetradecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by AGPS, CYP4Z1peroxisome, extracellular space

• CHEBI:16856Reach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by AGPSperoxisome, extracellular space, cytosolOne of 2 routes

• octadecanalReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by AGPS, ALDH3A2peroxisome, extracellular space

• anilineReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 8 morecytosol, mitochondrial matrix

• CHEBI:17312Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 6 morecytosol, mitochondrial matrixOne of 2 routes

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

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 7 morecytosol, mitochondrial matrix

• hexadecanalReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by AGPS, ALDH3B1, ALDH3B2, ALDH3A2peroxisome, extracellular space, cytosolOne of 2 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrix

• a 1,2-diacyl-sn-glycerolReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Diacylglycerol Phosphate Kinase (Homo Sapiens)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 8 morecytosol, mitochondrial matrix, nucleusOne of 10 routes

• CHEBI:17927Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 6 morecytosol, mitochondrial matrix

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

  Catalysed by AGPS, ALOX5peroxisome, extracellular space

• (5Z)-dodecenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by AGPS, UGT1A9, UGT2B7, UGT1A6 and 3 moreperoxisome, extracellular space

• (11Z)-docosenoyl-CoA(4-)Reach 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-cetoleic acid)

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

• (7Z)-tetradecenoyl-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 ((7Z)-tetradecenoic acid)

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

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

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

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. fatty acylamide amidohydrolase

  Catalysed by AGPS, FAAHperoxisome, extracellular space, cytosol

• CHEBI:27540Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 12 morecytosol, mitochondrial matrixOne of 6 routes

• dodecanalReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]

  Catalysed by AGPS, ALDH3A2peroxisome, extracellular space, endoplasmic reticulumOne of 3 routes

• CHEBI:28701Reach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrix, peroxisomeOne of 7 routes

• a fatty acidReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

  Catalysed by AGPS, ASAH1, ACER2, ACER1 and 2 moreperoxisome, cytosol

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. N-acylsphingosine amidohydrolase
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

  Catalysed by AGPS, ASAH1, ACER2, ACER1 and 4 moreperoxisome, cytosolOne of 2 routes

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolReach 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 + H2O = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + phosphate

  Catalysed by AKR1A1, EPHX2cytosol

• 12-hydroxydodecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by AGPS, CYP4A11, CYP4A22peroxisome, extracellular space, cytosolOne of 2 routes

• taurineReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 7 morecytosol, mitochondrial matrixOne of 2 routes

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

  Catalysed by AGPS, FAAHperoxisome, extracellular space, cytosol

• an N-acylsphing-4-enineReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. N-acylsphingosine amidohydrolase
  3. delta 4-desaturase, sphingolipid (dihydroceramide pool)

  Catalysed by AGPS, ASAH1, ACER2, ACER1 and 4 moreperoxisome, cytosolOne of 5 routes

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

  Catalysed by AGPS, DGAT1, LIPA, PNPLA4 and 2 moreperoxisome, extracellular space

• 16-hydroxyhexadecanoateReach from here →
  1. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by AGPS, CYP4F2, CYP4F3peroxisome, extracellular space, endoplasmic reticulumOne of 2 routes

• glycineReach from here →
  1. aldo-keto reductase (1-acylglycerol-3P pool)
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by AKR1A1, AGPAT2, LCLAT1, MBOAT1 and 9 morecytosol, mitochondrial matrixOne of 10 routes