(9Z)-octadecenoate

Three steps

• 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

• CHEBI:16857Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Threonine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 9 routes

• psychosineReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. H2O[r] + N-(9Z-octadecenoyl)-sphing-4-enine[r] = oleate[r] + sphingosine[r]
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreendoplasmic reticulum, cytosol

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

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

• oxalic acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and oxalate (cytosol to extracellular)

  Catalysed by SLC6A14, SLC26A6endoplasmic reticulum, cytosol, extracellular space

• a cholesterol esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  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 6 morecytosol, endoplasmic reticulumOne of 5 routes

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

  Catalysed by ALDH3A2cytosol, extracellular space

• L-isoleucineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and isoleucine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 10 routes

• CHEBI:17203Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Proline by the Apical Imino Amino Acid Transporters

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular spaceOne of 8 routes

• S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  3. (9Z,12Z)-octadecadienoyl-CoA + H2O = S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• N-octadecanoyl-heptadecasphing-4-enineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. heptadecasphing-4-enine + octadecanoyl-CoA = N-octadecanoyl-heptadecasphing-4-enine + CoA + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• myo-inositolReach from here →
  1. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  3. 1-(sn-glycero-3-phospho)-1D-myo-inositol glycerophosphohydrolase

  Catalysed by ABHD12, GDE1cytosolOne of 2 routes

• anilineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Acetyl-CoA:arylamine N-acetyltransferase

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

• CHEBI:17312Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

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

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

• cholesteryl 3-beta-D-glucosideReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreOne of 8 routes

• 7alpha-hydroxycholesterolReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• L-cysteineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 12 routes

• 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-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

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

• glycine betaineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of betaine and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A12endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA
  3. 1-(9Z-octadecenoyl)-glycerol + 1,2-di-(9Z-octadecenoyl)-glycerol = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + glycerol

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 13 moreOne of 3 routes

• a 1,2-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  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 7 morecytosolOne of 3 routes

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

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

• 4-methyl-2-oxopentanoateReach from here →
  1. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  2. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by PM20D1, BCAT2mitochondrial matrixOne of 4 routes

• CHEBI:17895Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Tyrosine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 11 routes

• CHEBI:17927Reach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

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

• butanoateReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ACOT8 and 5 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• 4-methylpentanalReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• 3-phenylpyruvateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. Phenylalanine Transaminase, Mitochondrial

  Catalysed by PM20D1, GOT2, TATmitochondrial matrixOne of 5 routes

• CHEBI:18019Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and lysine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 5 routes

• L-glutamineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Glutamine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 12 routes

• CHEBI:18095Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of trans-4-hydroxy-L-proline (cytosol to extracellular)

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular space

• N-carbamoyl-beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of 3-Ureidopropionate

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• 2-phenylethylamineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine carboxy-lyase (phenylethylamine-forming)

  Catalysed by PM20D1, DDCcytosol

• cholesteryl 3-beta-D-galactosideReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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, ACER1, ASAH2 and 3 moreOne of 2 routes

• cholesteryl 3-beta-D-xylosideReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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, ACER1, ASAH2 and 4 moreOne of 3 routes

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• S-methylmercury-L-cysteineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. S-methylmercury-L-cysteine(in) + L-phenylalanine(out) = S-methylmercury-L-cysteine(out) + L-phenylalanine(in)

  Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 4 routes

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositol + CoA
  3. 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD12, AGPAT3, AGPAT5, DDHD1

• (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. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, MOGAT2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Beta Oxidation Fatty Acid
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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