N-hexadecanoylethanolamine

Three steps

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-hexadecanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + hexadecanoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-hexadecanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 11 more

• 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. fatty acylamide amidohydrolase
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by NAAA, FAAH, PLA2G15cytosol

• (9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. fatty acylamide amidohydrolase
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by NAAA, FAAH, PLA2G15cytosol

• hexadecanedioateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum
  3. Fatty Acid Omega Oxidation (W-Ohc16->C16Dc)

  Catalysed by NAAA, CYP4F2, CYP4F3, ADH5 and 1 morecytosol, endoplasmic reticulum

• dodecanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Activation of dodecanedioic acid

  Catalysed by NAAAcytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Production of Sebacoylcarnitine

  Catalysed by NAAA, CPT1A, CPT1C, CPT1BcytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Production of Suberylcarnitine

  Catalysed by NAAA, CPT1A, CPT1C, CPT1BcytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by NAAAcytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 5 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bcytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 5 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by NAAA, CRAT, CROTcytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by NAAA, ACAA1, HSD17B4, EHHADH and 1 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Production of Hexadecanedioylcarnitine

  Catalysed by NAAA, CPT1A, CPT1C, CPT1BcytosolOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 7 routes

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by NAAA, ABHD11cytosol

• (11Z,14Z)-eicosadienoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• (17Z)-hexacosenoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• pristanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. fatty-acid-CoA ligase

  Catalysed by NAAA, SLC27A2cytosolOne of 2 routes

• 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 11 more

• 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 11 more

• 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + hexadecanoyl-CoA = 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 11 more

• undecanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by NAAA, ACSM4, ACSM1, ACSM2A and 3 morecytosolOne of 3 routes

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• tricosanoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by NAAAcytosol, extracellular spaceOne of 12 routes

• N-hexadecanoylhexadecasphinganineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. hexadecasphinganine + hexadecanoyl-CoA = N-hexadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 12 more

• 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-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 + hexadecanoyl-CoA = 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 11 more

• (5Z)-tetradecenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by NAAA, CRAT, CROTcytosol, endoplasmic reticulum, peroxisomeOne of 5 routes

• beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate
  3. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine

  Catalysed by FAAH, NAAA, FAAH2, ASAH1 and 3 more

• (3E)-decenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by NAAA, ACADM, ECHS1, ACAA2 and 1 morecytosol, mitochondrial matrix

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by NAAA, HADHA, ACAA2, HADHBcytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. stearoyl-CoA 9-desaturase (palmitoyl-CoA)

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

• tricosanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 4 routes