N-hexadecanoylethanolamine

Three steps

• (6Z,9Z,12Z)-octadecatrienoyl-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 (gamma-linolenate)

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

• butanoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by NAAA, SLC33A1, ESCO2, OXSMcytosol, endoplasmic reticulum, mitochondrial matrixOne of 11 routes

• dodecanoyl-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 (lauric acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 9 routes

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

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

• eicosanoyl-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 (eicosanoate)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 12 routes

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

  Catalysed by NAAA, SUCLG1, SUCLG2, SUCLA2cytosol, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-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 ((6Z,9Z)-octadecadienoic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 13 routes

• tetradecanoyl-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. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 8 morecytosol, mitochondrial matrixOne of 13 routes

• octanoyl-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. Beta Oxidation of Long Chain Fatty Acid

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, mitochondrial matrixOne of 22 routes

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

  Catalysed by NAAAcytosolOne of 5 routes

• octadecanoyl-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. fatty-acyl-CoA synthase (N-C18:0CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 22 routes

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 9 morecytosolOne of 2 routes

• (R)-2-hydroxyoctadecanoateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by NAAA, FA2Hcytosol

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

  Catalysed by NAAA, CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 9 routes

• sphing-4-enineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by NAAA, ASAH1, ACER2, ACER1 and 1 morecytosol, Golgi apparatusOne of 4 routes

• spermidineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by NAAA, SAT1, SAT2cytosolOne of 3 routes

• L-methionineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by NAAA, NAGScytosol, mitochondrial matrix

• CDP-ethanolamineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. ATP:ethanolamine O-phosphotransferase
  3. CTP:ethanolamine-phosphate cytidylyltransferase

  Catalysed by NAAA, CHKA, ETNK1, ETNK2 and 2 morecytosolOne of 3 routes

• sphinganine 1-phosphateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. ATP:ethanolamine O-phosphotransferase
  3. Sphinganine-1-phosphate pamlmitaldehyde-lyase

  Catalysed by NAAA, CHKA, ETNK1, ETNK2 and 2 morecytosolOne of 2 routes

• L-alanineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by NAAAcytosol, mitochondrial matrix

• a 1-O-alkyl-sn-glycero-3-phosphateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)
  3. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)

  Catalysed by NAAA, ENPP2cytosol

• L-asparagineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by NAAA, NAGScytosol, mitochondrial matrix

• L,L-cystathionineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by NAAA, NAGScytosol, mitochondrial matrix

• 3-oxosphinganineReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

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

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 6 morecytosol, peroxisomeOne of 2 routes

• an acyl-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. acyl-CoA pool formation and breakdown

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 3 routes

• (3Z)-dodecenoyl-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-oxomyrist-5-enoyl-CoA)

  Catalysed by NAAA, HADHA, ACAA2, HADHBcytosol, mitochondrial matrixOne of 3 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach 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

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by NAAA, SLC27A2, SLC27A5cytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by NAAA, SLC27A2, SLC27A5cytosolOne of 4 routes

• decanoyl-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 (decanoic acid)

  Catalysed by NAAA, ACSM4, ACSM1, ACSM2A and 3 morecytosolOne of 7 routes

• (2E)-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. trans-hexadec-2-enoyl-CoA reductase

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 6 morecytosol, mitochondrial matrixOne of 9 routes

• (9Z)-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. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 15 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by NAAA, CPT1A, CPT1Bcytosol

• 2-deoxy-D-ribose 5-phosphateReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. ethanolamine ammonia-lyase (acetaldehyde-forming)
  3. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde

  Catalysed by NAAA, DERAcytosol

• CHEBI:63544Reach 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 (adrenic acid)

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

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

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

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

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

• hexacosanoyl-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 (cerotic acid)

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

• tetracosanoyl-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 (lignocerate)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 10 routes

• docosanoyl-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 (behenic acid)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 5 morecytosolOne of 9 routes

• N-hexadecanoyl-(4R)-hydroxysphinganineReach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. (4R)-hydroxysphinganine + hexadecanoyl-CoA = N-hexadecanoyl-(4R)-hydroxysphinganine + CoA + H(+)

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

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

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 13 more

• 3-oxooctadecanoyl-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. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by NAAA, SLC27A2, ACSL4, ACSL3 and 12 morecytosolOne of 3 routes

• (2E)-octadecenoyl-CoAReach from here →
  1. H2O[c] + Hexadecenoyl Ethanolamide, C16:1-Ethanolamide (Delta 9)[c] = ethanolamine[c] + palmitate[c]
  2. Fas180
  3. Carnitine O-Palmitoyltransferase

  Catalysed by NAAA, CPT1A, CPT1C, CPT1BcytosolOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-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 (stearidonic acid)

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

• (8Z,11Z,14Z)-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 13 routes

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

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

• 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by FAAH, NAAA, FAAH2, SLC27A2 and 13 more

• 1-tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N-hexadecanoylethanolamine + H2O = ethanolamine + hexadecanoate
  2. hexadecanoate + ATP + CoA = hexadecanoyl-CoA + AMP + diphosphate
  3. 1-tetradecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + hexadecanoyl-CoA = 1-tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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