ethanolamine

Three steps

• CHEBI:16566Reach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. 3-sn-phosphatidate phosphohydrolase

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 4 morecytosolOne of 2 routes

• CHEBI:16856Reach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by FAAH, FAAH2cytosol, extracellular spaceOne of 2 routes

• (R)-3-hydroxybutyric acidReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. transport of (R)-3-hydroxybutanoate and acetate (cytosol to extracellular)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 4 morecytosol, extracellular spaceOne of 2 routes

• 17alpha-hydroxyprogesteroneReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol, endoplasmic reticulum

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. CTP:ethanolamine-phosphate cytidylyltransferase
  3. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 3 morecytosol

• hexadecanalReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. Sphinganine-1-phosphate pamlmitaldehyde-lyase

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 1 morecytosol, endoplasmic reticulumOne of 2 routes

• 4-methylumbelliferyl acetateReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 3 morecytosol

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by FAAH, FAAH2, UGT1A9, UGT2B7 and 4 morecytosol

• 17alpha-hydroxypregnenoloneReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol, endoplasmic reticulum

• CHEBI:29052Reach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. deoxyribose-phosphate aldolase
  3. deoxyribose-phosphate aldolase

  Catalysed by DERAcytosol

• formic acidReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. transport of acetate and formate (cytosol to extracellular)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 3 morecytosol, extracellular spaceOne of 2 routes

• propionic acidReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. transport of acetate and propanoate (cytosol to extracellular)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 4 morecytosol, extracellular spaceOne of 2 routes

• butyric acidReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. transport of acetate and butyrate (cytosol to extracellular)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 4 morecytosol, extracellular spaceOne of 2 routes

• fatty acidReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAH, FAAH2cytosolOne of 4 routes

• (S)-lactic acidReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. transport of acetate and L-lactate (cytosol to extracellular)

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 6 morecytosol, extracellular spaceOne of 2 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. fatty acid amide hydrolase (2-arachidonoylglycerol)

  Catalysed by FAAH, FAAH2cytosol

• 2-deoxy-alpha-D-ribose 1-phosphateReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde
  3. 2-deoxy-alpha-D-ribose 1-phosphate = 2-deoxy-D-ribose 5-phosphate

  Catalysed by DERA, PGM2cytosol

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by FAAH, FAAH2, SLC27A2, ACSL4 and 9 morecytosol

• prostaglandin H2Reach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. prostaglandin-endoperoxide synthase (arachidonate)

  Catalysed by FAAH, FAAH2, PTGS1, PTGS2cytosolOne of 3 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by FAAH, FAAH2, ALOX5, ALOX15 and 1 morecytosol

• (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by FAAH, FAAH2, ALOX15B, ALOX15 and 1 morecytosol

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by FAAH, FAAH2, ALOX5cytosol

• leukotriene A4Reach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

  Catalysed by FAAH, FAAH2, ALOX5cytosol

• N-acetyl-D-glucosamine 6-phosphateReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol

• sphinganineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. Sphinganine-1-phosphate pamlmitaldehyde-lyase
  3. sphinganine 1-phosphate + H2O = sphinganine + phosphate

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 3 morecytosol

• N-acetylputrescineReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol

• N(8)-acetylspermidineReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. Acetaldehyde:NAD+ oxidoreductase
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by ALDH3A1, ALDH3B1, ALDH1A3, ALDH3B2 and 1 morecytosol

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, FAAH2, PM20D1cytosol

• D-glyceraldehyde 3-phosphateReach from here →
  1. ethanolamine ammonia-lyase (acetaldehyde-forming)
  2. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde
  3. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde

  Catalysed by DERAcytosol

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. CTP:ethanolamine-phosphate cytidylyltransferase
  3. 1-O-alkyl-2-acyl-sn-glycerol + CDP-ethanolamine = a 1-O-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine + CMP + H(+)

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 2 morecytosol

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. cytochrome P450 (arachidonate)

  Catalysed by FAAH, FAAH2, CYP4F8cytosol, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. CTP:ethanolamine-phosphate cytidylyltransferase
  3. CDP-ethanolamine + a 1,2-diacyl-sn-glycerol = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CMP + H(+)

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 3 morecytosol

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. CTP:ethanolamine-phosphate cytidylyltransferase
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + CDP-ethanolamine = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 2 morecytosol

• a 1-O-alkylglycerone 3-phosphateReach from here →
  1. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)
  2. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)
  3. a 1-O-alkylglycerone 3-phosphate + NADPH + H(+) = a 1-O-alkyl-sn-glycero-3-phosphate + NADP(+)

  Catalysed by ENPP2, DHRS7B

• 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. ATP:ethanolamine O-phosphotransferase
  2. CTP:ethanolamine-phosphate cytidylyltransferase
  3. CDP-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)

  Catalysed by CHKA, ETNK1, ETNK2, CHKB and 2 morecytosol

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by FAAH, FAAH2, ALOX12Bcytosol

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by FAAH, FAAH2, ALOX12cytosolOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by FAAH, FAAH2cytosol

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. arachidonic acid:oxygen 1-oxidoreductase

  Catalysed by FAAH, FAAH2, CYP1A1, CYP1A2 and 25 morecytosolOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by FAAH, FAAH2, CYP2C9cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by FAAH, FAAH2, CYP1A1, CYP1A2 and 3 morecytosol

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by FAAH, FAAH2, PTGS2cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by FAAH, FAAH2, PTGS2cytosolOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by FAAH, FAAH2, PTGS2cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by FAAH, FAAH2, ALOX12cytosolOne of 2 routes

• prostaglandin G2Reach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by FAAH, FAAH2, PTGS1, PTGS2cytosol, endoplasmic reticulumOne of 2 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by FAAH, FAAH2, CYP2C9cytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. unspecific monooxygenase (arachidonate)

  Catalysed by FAAH, FAAH2, CYP1A1, CYP1A2 and 25 morecytosolOne of 4 routes