butanoyl-CoA

Three steps

• (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 5 moremitochondrial matrix, cytosol, endoplasmic reticulum

• 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 25 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 4 routes

• S-octanoyl-4'-phosphopantetheineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + H2O = S-octanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, CROT and 3 morecytosol, mitochondrial matrix

• decanoyl-4'-phosphopantetheineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + H2O = decanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 6 morecytosol

• S-dodecanoyl-4'-phosphopantetheineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + H2O = S-dodecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 9 morecytosol

• 17-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 25 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• tetradecanoyl-4'-phosphopantetheineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + H2O = tetradecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 9 morecytosol

• 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1mitochondrial matrix, cytosol, endoplasmic reticulum

• an acyl-4'-phosphopantetheineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + H2O = an acyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 6 morecytosol, Golgi apparatus

• tauroursodeoxycholateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine to tauroursodeoxycholate conversion

  Catalysed by CPT1A, CPT1C, CPT1B, BAATcytosolOne of 2 routes

• glycoursodeoxycholateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine to glycoursodeoxycholate conversion

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 2 morecytosol, mitochondrial matrixOne of 2 routes

• prostaglandin G1Reach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1

  Catalysed by SLC33A1, ESCO2, OXSM, PTGS2mitochondrial matrix, cytosol, endoplasmic reticulum

• prostaglandin E3Reach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and L-lactate (cytosol to extracellular)
  3. Transport of Prostaglandin E3, Lactate Antiport

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP3A4 and 1 moremitochondrial matrix, cytosol, endoplasmic reticulum

• prostaglandin A2Reach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and L-lactate (cytosol to extracellular)
  3. Transport of Prostaglandin A2, Lactate Antiport

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• prostaglandin J2Reach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and L-lactate (cytosol to extracellular)
  3. Transport of Prostaglandin J2, Lactate Antiport

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• 15-oxoprostaglandin F2alphaReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and L-lactate (cytosol to extracellular)
  3. Transport of 15-Keto-Prostaglandin F2A, Lactate Antiport

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular spaceOne of 2 routes

• leukotriene F4Reach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. leukotriene F4 hydrolysis

  Catalysed by CPT1A, CPT1C, CPT1B, ZDHHC11B and 31 morecytosol

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by SLC33A1, ESCO2, OXSM, ALOX15mitochondrial matrix, cytosol, endoplasmic reticulum

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by SLC33A1, ESCO2, OXSM, ALOX15mitochondrial matrix, cytosol, endoplasmic reticulum

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. transport of arachidonate (cytosol to extracellular)

  Catalysed by SLC33A1, ESCO2, OXSM, SLCO1B1mitochondrial matrix, cytosol, endoplasmic reticulum, extracellular spaceOne of 8 routes

• N-(9Z-octadecenoyl)glycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

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

  Catalysed by SLC33A1, ESCO2, OXSM, PM20D1mitochondrial matrix, cytosol, endoplasmic reticulum

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLC33A1, ESCO2, OXSM, PM20D1mitochondrial matrix, cytosol, endoplasmic reticulum

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

  Catalysed by SLC33A1, ESCO2, OXSM, PM20D1mitochondrial matrix, cytosol, endoplasmic reticulum

• N-octadecanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosolOne of 2 routes

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosolOne of 2 routes

• all-trans-4-hydroxyretinoateReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and retinoate (cytosol to extracellular)
  3. cytochrome P450 (retinoate)

  Catalysed by ACOT12, SLC16A4, SLC16A5, CYP26A1cytosol, extracellular spaceOne of 3 routes

• N-acetylcadaverineReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of acetate and butyrate (cytosol to extracellular)
  3. N-acetylcadaverine + H2O = cadaverine + acetate

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A7 and 2 morecytosol, extracellular space

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 25 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 25 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP2C9mitochondrial matrix, cytosol, endoplasmic reticulum

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP1A1 and 25 moremitochondrial matrix, cytosol, endoplasmic reticulum

• 2-hydroxyoctanoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, CROT and 1 morecytosol, mitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 6 morecytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• 11-cis-retinyl tetradecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosolOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• 13-cis-retinyl tetradecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• tetradecyl tetradecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by ACOT12, SLC16A4, SLC16A5, UGT1A1 and 2 morecytosol, extracellular space, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by ACOT12, SLC16A4, SLC16A5, CYP1A1 and 24 morecytosol, extracellular spaceOne of 2 routes

• a phenyl acetateReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of acetate and butyrate (cytosol to extracellular)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A7 and 4 morecytosol, extracellular space

• N-hexadecanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

• N-dodecanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosolOne of 2 routes

• N-decanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ACSM4 and 6 morecytosolOne of 2 routes