fatty acid

Three steps

• an N-octadecanoyl-sphingoid baseReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 moreextracellular space, cytosol

• 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerol

  Catalysed by FAAH, ALOX15Bextracellular space, cytosol

• 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreextracellular space

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (linoleate)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moreextracellular space, cytosol

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (linoleate)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moreextracellular space, cytosol

• (7Z)-octadecenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosolOne of 5 routes

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Arachidonate:oxygen oxidoreductase
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by PTGS1, PTGS2, PTGESextracellular space, endoplasmic reticulum

• CHEBI:15345Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 moreextracellular space, cytosolOne of 2 routes

• cholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 moreextracellular space, cytosol, nucleus

• acetylcholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of acetylcholine (cytosol to extracellular)

  Catalysed by SLCO1B1, SLCO1B3extracellular space, cytosolOne of 4 routes

• CHEBI:15380Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. Production of Tiglylcarnitine

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 moreextracellular space, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 moreextracellular space, cytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• CHEBI:15519Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosol, peroxisomeOne of 2 routes

• phenylacetyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. Phenylacetate:CoA ligase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 1 moreextracellular space, cytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Utilized Transport
  3. Active Transport

  No catalyst recordedextracellular space, endoplasmic reticulum, cytosol, mitochondrial matrixOne of 46 routes

• L-leucineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by PM20D1extracellular space

• (7S,14S)-dihydroperoxy-(4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate
  3. (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S,14S)-dihydroperoxy-(4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5, ALOX15, ALOX12extracellular space

• 1-(10Z-heptadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  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, ACSL3, ACSL1, ACSBG2 and 5 moreextracellular space

• CHEBI:15650Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by SLCO1B1extracellular space, cytosolOne of 6 routes

• S-(9Z-octadecenoyl)-4'-phosphopantetheineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. (9Z)-octadecenoyl-CoA + H2O = S-(9Z-octadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 5 moreextracellular space

• S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + H2O = S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreextracellular space

• betaine aldehydeReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by PTGS1, PTGS2, CHDHextracellular space

• CHEBI:15727Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 moreextracellular space, cytosol

• CHEBI:15746Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 moreextracellular space, cytosolOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

  Catalysed by GNPATextracellular space, cytosol

• bromideReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by MGST3, GSTA4, GSTA1, GSTA2 and 13 moreextracellular space, cytosolOne of 2 routes

• phosphatidylethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 1 moreextracellular space, cytosolOne of 2 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1extracellular space, cytosolOne of 2 routes

• cholesterolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  3. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 moreextracellular spaceOne of 8 routes

• hexadecan-1-olReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Palmitate:CoA ligase (AMP-forming)
  3. formate dehydrogenase (palmitoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moreextracellular space, cytosol, peroxisome

• 11-cis-retinolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 moreextracellular space, cytosolOne of 2 routes

• lithocholic acidReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of lithocholate (cytosol to extracellular)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• phosphatidic acidReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 9 routes

• oxaloacetateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. (R)-malate + A = oxaloacetate + AH2

  Catalysed by PTGS1, PTGS2, D2HGDHextracellular spaceOne of 2 routes

• (S)-lactateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)

  Catalysed by PTGS1, PTGS2, SLCO2A1extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• formaldehydeReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by PTGS1, PTGS2, KDM1A, KDM1Bextracellular spaceOne of 3 routes

• ferrocytochrome cReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Linoleate:oxygen 13-oxidoreductase
  3. 13(S)-HPODE to 13-oxy-radical-octadecadienoate conversion

  Catalysed by ALOX15B, ALOX15extracellular space, cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

  Catalysed by GPAT3, GPAT2, GPAT4, GPAMextracellular space, cytosol, mitochondrial matrix

• bilirubin IXalphaReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of bilirubin (cytosol to extracellular)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• a cholesterol esterReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + cholesterol = a cholesterol ester + CoA

  Catalysed by SOAT2, SOAT1extracellular space, cytosol

• taurolithocholateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• CHEBI:17208Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. glutathione:dehydroascorbate oxidoreductase

  No catalyst recordedextracellular space, cytosol

• homocysteineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Formation of Homocystine

  No catalyst recordedextracellular space, cytosol

• S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + H2O = S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moreextracellular space, cytosol

• S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (linoleate)
  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 5 moreextracellular space, cytosol

• S-(9Z-hexadecenoyl)-4'-phosphopantetheineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + H2O = S-(9Z-hexadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moreextracellular space, cytosol