chenodeoxycholate

Three steps

• CHEBI:15345Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by SLC27A5, BAAT, AACScytosol, peroxisomeOne of 2 routes

• cholineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by SLC27A5, BAAT, CHATcytosol, peroxisome, nucleusOne of 6 routes

• CHEBI:15380Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC27A5, BAAT, ALAS1, CPNE7cytosol, peroxisome, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by SLC27A5, BAAT, GLYAT, GLYATL2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Tiglylcarnitine

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1Bcytosol, peroxisomeOne of 2 routes

• isobutyryl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC27A5, BAAT, HADHA, ACAA2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLC27A5, BAAT, GLYATcytosol, peroxisome, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLC27A5, BAAT, GLYAT, GLYATL2 and 1 morecytosol, peroxisome, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 14 routes

• palmitoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLC27A5, BAAT, SLC27A2, ACSL4 and 6 morecytosol, peroxisomeOne of 11 routes

• oleoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLC27A5, BAAT, CPT1A, CPT1C and 1 morecytosol, peroxisomeOne of 11 routes

• phenylacetyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Phenylacetate:CoA ligase

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 3 routes

• propionyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A5, BAAT, ACSS3, ACSS2 and 1 morecytosol, peroxisomeOne of 43 routes

• 12(S)-HPETEReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX12extracellular space, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX15B and 1 moreextracellular space, cytosolOne of 4 routes

• 5(S)-HPETEReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, ALOX5extracellular space, cytosol

• CHEBI:15727Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by SLC27A5, BAAT, NAA10cytosol, peroxisome

• CHEBI:15746Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by SLC27A5, BAAT, SAT1, SAT2cytosol, peroxisomeOne of 2 routes

• bromideReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3, MGST3 and 16 moreextracellular space, cytosolOne of 2 routes

• beta-D-glucoseReach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. D-glucose 1-epimerase

  Catalysed by GBA2, GALMcytosol

• a halide anionReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by CYP8B1, ABCC4, GSTT4, GSTA4 and 21 moreinner side of the membrane, outer side of the membrane

• CHEBI:16174Reach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. dATP:D-glucose 6-phosphotransferase

  Catalysed by GBA2, HK1, HK2, HK3 and 1 morecytosol

• sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. steroid sulfatase (sulfoglycolithocholate)

  Catalysed by SLCO1A2, SLCO1B3, STSextracellular space, cytosolOne of 7 routes

• D-glucono-1,5-lactoneReach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. D-glucose + NAD(+) = D-glucono-1,5-lactone + NADH + H(+)

  Catalysed by GBA2, H6PDOne of 2 routes

• 11-cis-retinolReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A5, BAAT, DGAT1, LRAT and 3 morecytosol, peroxisome

• iodideReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. 3,3',5-triiodo-L-thyronine,iodide:acceptor oxidoreductase (iodinating)

  Catalysed by SLCO1A2, SLCO1B3, DIO1, DIO2extracellular space, cytosolOne of 9 routes

• oxaloacetateReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. ATP citrate lyase (citrate)

  Catalysed by SLC27A5, BAAT, ACLYcytosol, peroxisome

• (S)-lactateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2(out) + 2 (S)-lactate(in) = prostaglandin E2(in) + 2 (S)-lactate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLCO2A1extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 14 routes

• taurochenodeoxycholate 3-sulfateReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase
  3. taurochenodeoxycholate + 3'-phosphoadenylyl sulfate = taurochenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLC27A5, BAAT, SULT2A1cytosol, peroxisome

• dopamine quinoneReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. Peroxidase

  Catalysed by SLCO1A2, SLCO1B3, MPOextracellular space, cytosol, lysosomeOne of 4 routes

• CHEBI:17208Reach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. glutathione:dehydroascorbate oxidoreductase

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3extracellular space, cytosol

• homocysteineReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. solute carrier organic anion transporter (cholate)
  3. Formation of Homocystine

  Catalysed by CYP8B1, SLCO1A2, SLCO1B3extracellular space, cytosol

• dehydroascorbic acidReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of dopamine (cytosol to extracellular)
  3. dopamine,ascorbate:oxygen oxidoreductase (beta-hydroxylating)

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosol

• estroneReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. Estrone 3-sulfate sulfohydrolase

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, STSextracellular space, cytosolOne of 3 routes

• propanoateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. propanoate(in) + estrone 3-sulfate(out) = propanoate(out) + estrone 3-sulfate(in)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, SLC22A9extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• anilineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by SLC27A5, BAAT, NAT2, NAT1cytosol, peroxisome

• CHEBI:17312Reach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SLC27A5, BAATcytosol, peroxisomeOne of 2 routes

• sulfiteReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by CYP8B1, ABCC4, TSTD1inner side of the membrane, outer side of the membraneOne of 2 routes

• L-cysteineReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by SLC27A5, BAAT, NAGScytosol, peroxisome, mitochondrial matrixOne of 2 routes

• 3,3',5-triiodo-L-thyronine sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. aryl sulfotransferase (PAPS)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A4 and 2 moreextracellular space, cytosolOne of 2 routes

• L-thyroxine sulfateReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. L-thyroxine + 3'-phosphoadenylyl sulfate = L-thyroxine sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1A2, SLCO1B3, SULT1A3, SULT1A4 and 1 moreextracellular space, cytosol

• 3,3'-diiodo-L-thyronineReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. thyroxine 5'-deiodinase (3,3-diiodo-L-thyronine)

  Catalysed by SLCO1A2, SLCO1B3, DIO1, DIO3 and 1 moreextracellular space, cytosolOne of 3 routes

• N-acetylserotoninReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of serotonin (cytosol to extracellular)
  3. acetyl-CoA:aralkylamine N-acetyltransferase

  Catalysed by SLCO1A2, SLCO1B3, AANATextracellular space, cytosol

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. chenodeoxycholate:CoA ligase (AMP-forming)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by SLC27A5, BAAT, HADHA, ACADVL and 1 morecytosol, peroxisome, mitochondrial matrix

• lactoseReach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. D-glucose + UDP-alpha-D-galactose = lactose + UDP + H(+)

  Catalysed by GBA2, B4GALT2, B4GALT1

• urateReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. urate(out) + glutathione(in) = urate(in) + glutathione(out)

  Catalysed by CYP8B1, ABCC4, SLC22A13inner side of the membrane, outer side of the membrane

• 5-hydroxy-L-tryptophanReach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of serotonin (cytosol to extracellular)
  3. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2

  Catalysed by SLCO1A2, SLCO1B3, DDCextracellular space, cytosol

• prostaglandin F1Reach from here →
  1. solute carrier organic anion transporter (chenodiol)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin E1 + NADPH + H(+) = prostaglandin F1 + NADP(+)

  Catalysed by SLCO1A2, SLCO1B3, SLCO1B1, DHRS1extracellular space, cytosol

• CHEBI:17808Reach from here →
  1. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)
  2. beta-D-glucosyl-(1->3)-O-chenodeoxycholate + H2O = chenodeoxycholate + D-glucose
  3. ITP:D-glucose 6-phosphotransferase

  Catalysed by GBA2, HK1, HK2, HK3 and 1 morecytosol

• methylarsonous acidReach from here →
  1. chenodeoxycholate + reduced [NADPH--hemoprotein reductase] + O2 = cholate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. cholate(in) + glutathione(in) + ATP + H2O = cholate(out) + glutathione(out) + ADP + phosphate + H(+)
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by CYP8B1, ABCC4, GSTO1, GSTO2inner side of the membrane, outer side of the membrane