octadecanoate

Three steps

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

  Catalysed by ALOX15B, ALOX15cytosol, extracellular spaceOne of 4 routes

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

  Catalysed by ALOX5cytosol, extracellular space

• 1-(10Z-heptadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• CHEBI:15650Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 40 morecytosolOne of 2 routes

• S-(9Z-octadecenoyl)-4'-phosphopantetheineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. (9Z)-octadecenoyl-CoA + H2O = S-(9Z-octadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• CHEBI:15727Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:15746Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol

• phosphatidylethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• hexadecan-1-olReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. formate dehydrogenase (palmitoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisome

• 11-cis-retinyl hexadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, peroxisomeOne of 4 routes

• 11-cis-retinolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol

• phosphatidic acidReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol

• oxaloacetateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. ATP citrate lyase (citrate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:16566Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• pregnenoloneReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

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

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• psychosineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

  Catalysed by ASAH1, ACER2, ASAH2cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes

• a cholesterol esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol, endoplasmic reticulumOne of 5 routes

• anilineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol

• CHEBI:17312Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisomeOne of 4 routes

• cholesteryl 3-beta-D-glucosideReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 moreOne of 8 routes

• 7alpha-hydroxycholesterolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• L-cysteineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrix

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

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2cytosol, extracellular spaceOne of 2 routes

• 26-hydroxycholesterolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix

• glycerolReach from here →
  1. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  2. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  3. 2-(9Z-octadecenoyl)-glycerol + H2O = glycerol + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD11, ABHD16A, LIPE, PLB1 and 4 more

• a 1,2-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 3 routes

• a triacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• CHEBI:17927Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• 4-methylpentanalReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• cholesteryl 3-beta-D-galactosideReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 moreOne of 2 routes

• cholesteryl 3-beta-D-xylosideReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 moreOne of 2 routes

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

  Catalysed by ALOX5cytosol, extracellular space

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  2. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ABHD11, MOGAT2, MOGAT1

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  2. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ABHD11, MOGAT2, MOGAT1

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  2. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)
  3. eicosanoyl-CoA + 2-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by ABHD11, MOGAT2, MOGAT1