N-(9Z-octadecenoyl)glycine

Three steps

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

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 12 routes

• an N-acylsphinganineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by FAAH, PM20D1, ASAH1, ACER2 and 3 morecytosol

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

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 12 routes

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

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 18 routes

• (15Z)-tetracosenoateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 17 routes

• (11Z)-eicosenoateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, PM20D1cytosol, extracellular spaceOne of 12 routes

• L-lysineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine(out) + L-lysine(in) = L-ornithine(in) + L-lysine(out)

  Catalysed by FAAH, PM20D1, GATM, SLC25A2 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• D-lysineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. L-Arginine:glycine amidinotransferase
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by FAAH, PM20D1, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• putrescineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. L-Arginine:glycine amidinotransferase
  3. L-ornithine carboxy-lyase (putrescine-forming)

  Catalysed by FAAH, PM20D1, GATM, ODC1cytosolOne of 4 routes

• D-arginineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. L-Arginine:glycine amidinotransferase
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by FAAH, PM20D1, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of glycine and methionine (cytosol to extracellular)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by FAAH, PM20D1, SLC7A5, IL4I1extracellular space, cytosol

• di-mu-sulfido-diiron(2+)Reach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. De novo synthesis of 2Fe2S

  Catalysed by FAAH, PM20D1, SLC3A2, SLC7A5 and 8 moreextracellular space, cytosol, mitochondrial matrix

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL3 and 7 more

• serotoninReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and serotonin (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, GSS, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 2 routes

• (S)-3-methyl-2-oxopentanoateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate

  Catalysed by FAAH, PM20D1, SLC7A5, BCAT2 and 1 moreextracellular space, cytosol

• D-cysteineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of alanine and glycine (cytosol to extracellular)
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by FAAH, PM20D1, SLC3A2, SLC7A5 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-serineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of alanine and glycine (cytosol to extracellular)
  3. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)

  Catalysed by FAAH, PM20D1, SLC3A2, SLC7A5 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 10 routes

• 3-methyl-2-oxovaleric acidReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of glycine and isoleucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by FAAH, PM20D1, SLC7A5, BCAT1extracellular space, cytosolOne of 2 routes

• 3-(4-hydroxyphenyl)pyruvateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. transport of glycine and tyrosine (cytosol to extracellular)
  3. L-tyrosine:2-oxoglutarate aminotransferase

  Catalysed by FAAH, PM20D1, SLC7A5, GOT2 and 2 moreextracellular space, cytosolOne of 7 routes

• taurocholateReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (GSH)

  Catalysed by FAAH, PM20D1, GSS, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 3 routes

• tert-butanolReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. tert-butyl hydroperoxide + 2 glutathione = tert-butanol + glutathione disulfide + H2O

  Catalysed by FAAH, PM20D1, GSS, CLIC2 and 4 more

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL4 and 8 morecytosol, endoplasmic reticulumOne of 2 routes

• Cu(+)Reach from here →
  1. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. Cu(2+)(out) + L-ascorbate(in) = Cu(+)(out) + monodehydro-L-ascorbate radical(in) + H(+)

  Catalysed by PAM, CYBRD1inner side of the membrane, outer side of the membraneOne of 3 routes

• gamma-Glu-AlaReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by FAAH, PM20D1, GSS, GGT1 and 5 morecytosol, extracellular spaceOne of 2 routes

• taurineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by FAAH, PM20D1, BAATperoxisome, cytosolOne of 4 routes

• 1,2-di-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL3 and 12 moreOne of 3 routes

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL3 and 9 moreOne of 2 routes

• 3,3',5-triiodo-L-thyronineReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and triiodothyronine (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, GSS, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 2 routes

• (R)-methylmalonyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by FAAH, PM20D1, BAAT, ALDH6A1peroxisome, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by FAAH, PM20D1, BAATperoxisome, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by FAAH, PM20D1, BAAT, ACP2peroxisome, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by FAAH, PM20D1, BAATperoxisome, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by FAAH, PM20D1, BAAT, ACAA1 and 1 moreperoxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by FAAH, PM20D1, BAAT, SLC27A2 and 7 moreperoxisome, cytosolOne of 7 routes

• benzoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. Hippurate (Benzoylglycinate) Formation
  3. benzoyl-CoA + glycine = N-benzoylglycine + CoA + H(+)

  Catalysed by FAAH, PM20D1, GLYATmitochondrial matrix

• butanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by FAAH, PM20D1, SLC33A1, ESCO2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 11 routes

• dodecanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by FAAH, PM20D1, BAAT, SLC27A2 and 7 moreperoxisome, cytosolOne of 10 routes

• glutaryl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Glutaryl Carnitine

  Catalysed by FAAH, PM20D1, BAAT, CPT1A and 2 moreperoxisome, cytosolOne of 2 routes

• hexadecanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by FAAH, PM20D1, GLYATL3

• eicosanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by FAAH, PM20D1, BAAT, SLC27A2 and 7 moreperoxisome, cytosolOne of 12 routes

• itaconyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by FAAH, PM20D1, BAAT, SUCLG1 and 2 moreperoxisome, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL4 and 7 morecytosolOne of 16 routes

• tetradecanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by FAAH, PM20D1, BAAT, SLC27A2 and 7 moreperoxisome, cytosolOne of 12 routes

• octanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Beta Oxidation Fatty Acid

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL4 and 8 morecytosol, mitochondrial matrixOne of 22 routes

• phytanoyl-CoAReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. bile acid-CoA: amino acid N-acyltransferase
  3. phytanate-CoA ligase

  Catalysed by FAAH, PM20D1, BAATperoxisome, cytosolOne of 5 routes

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

  Catalysed by FAAH, PM20D1, SLC27A2, ACSL3 and 8 moreOne of 16 routes

• prostaglandin E1Reach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin E1 (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, GSS, SLCO2A1cytosol, extracellular spaceOne of 2 routes

• prostaglandin I2Reach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin I2 (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, GSS, SLCO2A1cytosol, extracellular spaceOne of 2 routes

• prostaglandin F2alphaReach from here →
  1. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, GSS, SLCO2A1cytosol, extracellular spaceOne of 2 routes