butanoyl-CoA

Three steps

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by SLC33A1, ESCO2, OXSM, ALOX12mitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• prostaglandin G2Reach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by SLC33A1, ESCO2, OXSM, PTGS1 and 1 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

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

• cholesteryl octadecanoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol, endoplasmic reticulumOne of 2 routes

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

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

• 1-hexadecanoyl-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-hexadecanoyl-sn-glycero-3-phosphate = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

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

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

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

• glycodeoxycholateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. deoxycholoyl-CoA to glycodeoxycholate conversion

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 1 morecytosolOne of 3 routes

• (12R)-hydroxy-(5Z,8Z,10E,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 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• sphinga-4E,14Z-dienineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 4 morecytosol, Golgi apparatus

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + CoA

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

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosol

• 14,15-epoxy-(5Z,8Z,11Z)-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 26 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 4 routes

• 8,9-epoxy-(5Z,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 3 routes

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

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

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

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

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

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

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

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

• O-octadecanoyl-(R)-carnitineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosol

• O-eicosanoyl-(R)-carnitineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

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

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 7 morecytosol

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 9 morecytosol, endoplasmic reticulumOne of 2 routes

• N-tetradecanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

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

• N-eicosanoylglycinateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

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

• N-docosanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

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

• N-hexacosanoylglycineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

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

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. butanoyl-CoA + H2O = butanoate + CoA + H(+)
  2. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ACOT8, ACAA2, ACOT11, ACOT12 and 4 moreinner side of the membrane, outer side of the membrane

• an N(2)-acyl-L-glutamineReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 5 morecytosol, Golgi apparatus

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 11 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 11 morecytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SOAT1cytosol

• a 3-oxoacyl-CoAReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 7 morecytosol, Golgi apparatus

• (18R)-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 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, CYP4F8mitochondrial matrix, cytosol, endoplasmic reticulum

• 15-hydroperoxy-(5Z,8Z,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 + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLC33A1, ESCO2, OXSM, ALOX15Bmitochondrial matrix, cytosol, endoplasmic reticulum

• 5-hydroperoxy-(6E,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 + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by SLC33A1, ESCO2, OXSM, ALOX15Bmitochondrial matrix, cytosol, endoplasmic reticulum

• taurochenodeoxycholateReach from here →
  1. carnitine O-palmitoyltransferase (butyryl-CoA)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by CPT1A, CPT1C, CPT1B, ACAA1 and 3 morecytosol, peroxisomeOne of 5 routes

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. Butyryl-CoA hydrolase
  2. transport of butyrate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by ACOT12, SLC16A4, SLC16A5, SLC16A3 and 6 morecytosol, extracellular space, mitochondrial matrix