butanoate

Three steps

• heptadecanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 5 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 5 routes

• nonadecanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 6 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 3 routes

• dodecanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Activation of dodecanedioic acid

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Production of Sebacoylcarnitine

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Production of Suberylcarnitine

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 5 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 5 routes

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5

  Catalysed by SLC22A9, SLCO1B1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 6 morecytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 8 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Production of Hexadecanedioylcarnitine

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 4 morecytosolOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 7 moremitochondrial matrix, cytosolOne of 7 routes

• pristanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. fatty-acid-CoA ligase

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 5 morecytosolOne of 2 routes

• undecanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 6 morecytosolOne of 3 routes

• 16alpha-hydroxyestroneReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. Estrone 3-sulfate sulfohydrolase
  3. unspecific monooxygenase (estrone)

  Catalysed by SLC22A9, STS, CYP1A1, CYP1A2 and 22 moreinner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• ursodeoxycholateReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by SLC22A9, SLCO1B1, SLCO1A2, SLCO1B3inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 3beta,7alpha-dihydroxyandrost-5-en-17-oneReach from here →
  1. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. 3beta-hydroxyandrost-5-en-17-one + reduced [NADPH--hemoprotein reductase] + O2 = 3beta,7alpha-dihydroxyandrost-5-en-17-one + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC22A9, STS, CYP7B1inner side of the membrane, outer side of the membrane, cytosol

• prostaglandin G2Reach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. transport of prostaglandin G2 (cytosol to extracellular)

  Catalysed by SLC22A9, SLCO1B1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. estrone 3-sulfate(out) + glutarate(in) = estrone 3-sulfate(in) + glutarate(out)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

  Catalysed by SLC22A9, SLC22A24, SLC22A8, SLC22A11inner side of the membrane, outer side of the membraneOne of 2 routes

• androst-5-ene-3,17-dioneReach from here →
  1. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)
  2. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase
  3. dehydroepiandrosterone:NAD+ oxidoreductase

  Catalysed by SLC22A9, STS, HSD3B1, HSD3B2inner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• pentanalReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. pentanoate(in) + estrone 3-sulfate(out) = pentanoate(out) + estrone 3-sulfate(in)
  3. pentanal + NAD(+) + H2O = pentanoate + NADH + 2 H(+)

  Catalysed by SLC22A9, ALDH9A1inner side of the membrane, outer side of the membrane

• (5Z)-tetradecenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 6 moremitochondrial matrix, cytosol, peroxisomeOne of 5 routes

• (3E)-decenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 8 morecytosol, mitochondrial matrix

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 7 morecytosol, mitochondrial matrix

• 4-hydroxyestroneReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC22A9, STS, CYP1A1, CYP1A2 and 4 moreinner side of the membrane, outer side of the membrane, cytosol

• 6alpha-hydroxyestroneReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 6alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC22A9, STS, CYP1A1inner side of the membrane, outer side of the membrane, cytosol

• 15alpha-hydroxyestroneReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. Estrone 3-sulfate sulfohydrolase
  3. estrone + reduced [NADPH--hemoprotein reductase] + O2 = 15alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC22A9, STS, CYP1A1inner side of the membrane, outer side of the membrane, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. butanoate + ATP + CoA = butanoyl-CoA + AMP + diphosphate
  2. carnitine O-palmitoyltransferase (butyryl-CoA)
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by ACSM1, ACSM2A, ACSM3, ACSM2B and 12 morecytosolOne of 4 routes

• thromboxane B2Reach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by SLC22A9, SLCO1B1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• taurochenodeoxycholateReach from here →
  1. butanoate(out) + estrone 3-sulfate(in) = butanoate(in) + estrone 3-sulfate(out)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by SLC22A9, SLCO1B1, SLCO1A2, SLC7A9 and 1 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes