(9Z)-octadecenamide

Three steps

• 1-octanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 7 more

• 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-dodecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 8 more

• 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 8 more

• 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 8 more

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 7 more

• 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-tetradecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 7 more

• 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-(9Z-octadecenyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 12 more

• 1-decanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 7 more

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 2 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) = 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by FAAH, FAAH2, ABHD12, CLN5

• docosanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• octadecanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• alpha-linolenic acidReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 13 routes

• elaidic acidReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 13 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

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

  Catalysed by PAM, CYB561D2, CYB561, CYBRD1 and 2 moreinner side of the membrane, outer side of the membrane

• chlorine(.)Reach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. Utilized Transport
  3. Carnitine Transport by Atb0

  Catalysed by FAAH, FAAH2, SLC6A14endoplasmic reticulum, cytosol, extracellular space

• glycolateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. glycolate + NADP(+) = glyoxylate + NADPH + H(+)

  Catalysed by PAM, GRHPR

• oxalateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. glyoxylate + O2 + H2O = oxalate + H2O2 + H(+)

  Catalysed by PAM, HAO1

• tetradecanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• hexacosanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• tetracosanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• an N-acylsphinganineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by FAAH, FAAH2, ASAH1, ACER2 and 3 morecytosol

• eicosanoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• (9Z)-hexadecenoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 18 routes

• (15Z)-tetracosenoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 14 routes

• (11Z)-eicosenoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  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, FAAH2, SLC27A2, ACSL3 and 7 more

• 3-(4-hydroxyphenyl)pyruvateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by PAM, AADAT

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL4 and 8 morecytosol, endoplasmic reticulumOne of 2 routes

• Cu(+)Reach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  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 membrane

• 1,2-di-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  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, FAAH2, SLC27A2, ACSL3 and 12 moreOne of 3 routes

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  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, FAAH2, SLC27A2, ACSL3 and 9 moreOne of 2 routes

• glycineReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O

  Catalysed by PAM, FAAH, PM20D1One of 16 routes

• butanoyl-CoAReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by FAAH, FAAH2, SLC33A1, ESCO2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL4 and 7 morecytosolOne of 2 routes

• octanoyl-CoAReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. Beta Oxidation Fatty Acid

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL4 and 8 morecytosol, mitochondrial matrix

• octadecanoyl-CoAReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  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, FAAH2, SLC27A2, ACSL3 and 8 more

• 2-oxoadipateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. L-2-aminoadipate + glyoxylate = 2-oxoadipate + glycine

  Catalysed by PAM, AADAT

• O-acetyl-(R)-carnitineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. Utilized Transport
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by FAAH, FAAH2, CPT1A, CPT1C and 1 moreendoplasmic reticulum, cytosolOne of 9 routes

• sphing-4-enineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. H2O[r] + N-(9Z-octadecenoyl)-sphing-4-enine[r] = oleate[r] + sphingosine[r]

  Catalysed by FAAH, FAAH2, ASAH1, ACER2 and 3 moreendoplasmic reticulumOne of 3 routes

• L-phenylalanineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by FAAH, FAAH2, PM20D1

• a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. a 1-acyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL3 and 7 more

• an acyl-CoAReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. long-chain-fatty-acid-CoA ligase (oleate)
  3. acyl-CoA pool formation and breakdown

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL4 and 6 morecytosol

• sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)

  Catalysed by FAAH, FAAH2, ABHD12

• kynurenateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. L-kynurenine + glyoxylate = kynurenate + glycine + H2O

  Catalysed by PAM, KYAT3, AADAT

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (9Z)-octadecenamide + H2O = (9Z)-octadecenoate + NH4(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 12 routes

• 5-amino-2-oxopentanoateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. L-ornithine + glyoxylate = 5-amino-2-oxopentanoate + glycine

  Catalysed by PAM, AGXT2

• monodehydro-L-ascorbate radicalReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  3. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by PAMOne of 12 routes

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  2. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by PAM, HOGA1