fatty acid

Three steps

• 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z)-octadecenoyl-CoA = 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol + CoA

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

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

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

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

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

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

• 1-heptadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Aextracellular space

• 1-heptadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Aextracellular space

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

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

• O-octadecanoyl-(R)-carnitineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

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

• O-eicosanoyl-(R)-carnitineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

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

• (5Z)-tetradecenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 9 moreextracellular space, cytosolOne of 10 routes

• O-(9Z)-octadecenoyl-(R)-carnitineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

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

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CRAT, CROTextracellular space, endoplasmic reticulum, cytosol, peroxisomeOne of 5 routes

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by ASAH1, ACER2, ASAH2, GBA1extracellular space

• (3E)-decenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 moreextracellular space, cytosol, mitochondrial matrix

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

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

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

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

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moreextracellular space, cytosol, endoplasmic reticulumOne of 2 routes

• 2-glyceryl-prostaglandin G2Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2

  Catalysed by FAAH, PTGS2extracellular space, cytosol

• 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach 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-O-(9Z-octadecenyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

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

• 1-decanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• N-tetradecanoylglycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

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

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 moreextracellular space, cytosol, mitochondrial matrix

• N-eicosanoylglycinateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

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

• N-docosanoylglycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

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

• N-hexacosanoylglycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

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

• an N(2)-acyl-L-glutamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by GLYATL1B, GLYATL1extracellular space, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (9E)-octadecenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 9 moreextracellular space, cytosolOne of 10 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by ALOX5, PTGES, MGST3, GPX1 and 3 moreextracellular space

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by ALOX5, ALOX15, ALOX12, GPX1 and 1 moreextracellular space

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by PTGS1, PTGS2, TBXAS1, CYP2S1 and 1 moreextracellular space, cytosol

• thromboxane B2Reach 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 SLCO1B1extracellular space, cytosolOne of 4 routes

• 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
  3. (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + NAD(+) = 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoate + NADH + H(+)

  Catalysed by PTGS2, HPGDextracellular space

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

  Catalysed by ACAA1, SCP2, ACAA2, HADHBextracellular space, cytosol

• 13-oxo-(9Z,11E)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Linoleate:oxygen 13-oxidoreductase
  3. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate = 13-oxo-(9Z,11E)-octadecadienoate + H2O

  Catalysed by ALOX15B, ALOX15, CYP1A1, CYP1A2 and 3 moreextracellular space, cytosol

• prostaglandin H1Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1
  3. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O

  Catalysed by PTGS2extracellular space

• 19-hydroxyprostaglandin H2Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGS1, PTGS2, CYP4F8extracellular space, cytosol

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. Linoleate:oxygen 13-oxidoreductase
  3. glutathione peroxidase (13(S)-HPODE)

  Catalysed by ALOX15B, ALOX15, GPX5, GPX1 and 7 moreextracellular space, cytosolOne of 2 routes

• taurochenodeoxycholateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. transport of arachidonate (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by SLCO1B1, SLCO1A2, SLC7A9, SLCO1B3extracellular space, cytosolOne of 4 routes