(9Z,12Z)-octadecadienoate

Three steps

• CHEBI:15699Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and homoserine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes

• CHEBI:15727Reach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 5 morecytosol

• formateReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)

  Catalysed by PTGS2, KDM1A, KDM1B, ALDH9A1

• CHEBI:15746Reach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 6 morecytosolOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, GNPATcytosol

• CHEBI:15971Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and histidine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes

• ferricytochrome cReach from here →
  1. (9Z,12Z)-octadecadienoate + O2 = (13S)-hydroperoxy-(9Z,11E)-octadecadienoate
  2. 13(S)-HPODE to 13-oxy-radical-octadecadienoate conversion
  3. 13(S)-HPODE to 13-oxy-radical-octadecadienoate conversion

  Catalysed by ALOX15, ALOX12cytosolOne of 4 routes

• methanethiolReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by PTGS2, KDM1A, KDM1B, SELENBP1

• phosphatidylethanolamineReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, LPCAT4 and 4 morecytosol

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, LPCAT4 and 3 morecytosol

• L-cystineReach from here →
  1. (9Z,12Z)-octadecadienoate + O2 = (13S)-hydroperoxy-(9Z,11E)-octadecadienoate
  2. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate + 2 glutathione = (13S)-hydroxy-(9Z,11E)-octadecadienoate + glutathione disulfide + H2O
  3. cystine to cysteine conversion

  Catalysed by ALOX15, ALOX12, GPX1, GSTA1 and 2 morecytosolOne of 5 routes

• 11-cis-retinolReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 9 morecytosolOne of 3 routes

• cob(II)alaminReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 cob(II)alamin + A + 2 H2O + 2 H(+) = 2 aquacob(III)alamin + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, MTRR

• phosphatidic acidReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, AGPAT2 and 8 morecytosol, mitochondrial matrixOne of 7 routes

• L-citrullineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of citrulline and cysteine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes

• iodideReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 22 routes

• L-valineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and valine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes

• L-arginineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of arginine and cysteine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 5 routes

• nitric oxideReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 nitrite + AH2 + 2 H(+) = 2 nitric oxide + A + 2 H2O

  Catalysed by PTGS2, AIFM1, PYROXD1, SUOX

• protein polypeptide chainReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. PROTEIN_BS

  Catalysed by PTGS2, MOCOScytosol

• 3'-deoxy-3',4'-didehydro-CTPReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. CTP + AH2 + S-adenosyl-L-methionine = 3'-deoxy-3',4'-didehydro-CTP + 5'-deoxyadenosine + L-methionine + A + H2O + H(+)

  Catalysed by PTGS2, AIFM1, PYROXD1, RSAD2

• (S)-2-hydroxyglutarateReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (S)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, L2HGDH

• CHEBI:16856Reach from here →
  1. (9Z,12Z)-octadecadienoate + O2 = (13S)-hydroperoxy-(9Z,11E)-octadecadienoate
  2. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate + 2 glutathione = (13S)-hydroxy-(9Z,11E)-octadecadienoate + glutathione disulfide + H2O
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by ALOX15, ALOX12, GPX1, GSTA1 and 8 morecytosolOne of 8 routes

• CHEBI:16857Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and threonine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. glycerol-3-phosphate 1-O-acyltransferase (linoleoyl-CoA)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by ACSL3, ACSBG2, SLC27A3, GPAT3 and 3 morecytosolOne of 9 routes

• a cholesterol esterReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion

  Catalysed by ACSL3, ACSBG2, SLC27A3, SOAT2 and 1 moreendoplasmic reticulumOne of 4 routes

• L-isoleucineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and isoleucine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• CHEBI:17203Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and proline (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes

• anilineReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 6 morecytosol

• CHEBI:17312Reach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 4 morecytosolOne of 2 routes

• 5'-deoxyadenosineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-SH + AH2 + 2 S-adenosyl-L-methionine = 2-methylsulfanyl-N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-H + 5'-deoxyadenosine + L-methionine + A + S-adenosyl-L-homocysteine + 2 H(+)

  Catalysed by PTGS2, AIFM1, PYROXD1, CDK5RAP1One of 4 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, LPCAT4 and 3 morecytosol

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. Lecithin Retinol Acyltransferase

  Catalysed by PTGS2, RETSAT, LRATcytosol

• all-trans-retinyl hexadecanoateReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-retinol + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA

  Catalysed by PTGS2, RETSAT, DGAT1, PNPLA4 and 3 moreOne of 2 routes

• 3,3',5'-triiodo-L-thyronine sulfateReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3',5'-triiodo-L-thyronine sulfate + iodide + A + H(+) = L-thyroxine sulfate + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, DIO1

• 3,3'-diiodo-L-thyronineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodo-L-thyronine sulfate + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine sulfate + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, DIO1One of 2 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 7 morecytosol, mitochondrial matrix

• CHEBI:17724Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. dimethylglycine dehydrogenase (formaldehyde)

  Catalysed by PTGS2, KDM1A, KDM1B, PDPR and 1 morecytosol

• glycine betaineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. choline + A = betaine aldehyde + AH2
  3. p-cumic alcohol:NAD+ oxidoreductase

  Catalysed by PTGS2, CHDH, ALDH7A1cytosolOne of 4 routes

• a 1,2-diacyl-sn-glycerolReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA

  Catalysed by ACSL3, ACSBG2, SLC27A3, MOGAT2 and 2 morecytosol

• a triacylglycerolReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, DGAT1 and 4 morecytosol

• CHEBI:17895Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and tyrosine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• all-trans-retinalReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. retinol: NADP+ oxidoreductase

  Catalysed by PTGS2, RETSAT, DHRS3, RDH10 and 4 morecytosolOne of 6 routes

• CHEBI:17927Reach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. (6Z,9Z)-octadecadienoyl-CoA hydrolase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACOT7 and 4 morecytosol

• CHEBI:18019Reach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and lysine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes

• a diacylglycerolReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. a triacylglycerol + all-trans-retinol = an all-trans-retinyl ester + a diacylglycerol

  Catalysed by PTGS2, RETSAT, PNPLA4, PNPLA2

• L-glutamineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and glutamine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC3A2, SLC7A5 and 1 moreextracellular space, cytosolOne of 4 routes

• O-octanoyl-(R)-carnitineReach from here →
  1. (9Z,12Z)-octadecadienoate + ATP + CoA = (9Z,12Z)-octadecadienoyl-CoA + AMP + diphosphate
  2. Beta Oxidation of Fatty Acid
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by ACSL3, ACSBG2, SLC27A3, ACADM and 2 moremitochondrial matrixOne of 4 routes

• 3',5'-diiodo-L-thyronineReach from here →
  1. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3',5'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5'-triiodo-L-thyronine + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, DIO3