KEGG   PATHWAY: pov00120
Entry
pov00120                    Pathway                                
Name
Primary bile acid biosynthesis - Paralichthys olivaceus (Japanese flounder)
Description
Bile acids are steroid carboxylic acids derived from cholesterol in vertebrates. The primary bile acids, cholic acid and chenodeoxycholic acid, are synthesized in the liver and conjugated with taurine or glycine before secretion via bile into the intestine. The conversion from cholesterol to cholic and chenodeoxycholic acids involves four steps: 1) the initiation of synthesis by 7alpha-hydroxylation of sterol precursors, 2) further modifications to the ring structures, 3) side-chain oxidation and shortening (cleavage) by three carbons, and 4) conjugation of the bile acid with taurine or glycine.
Class
Metabolism; Lipid metabolism
Pathway map
pov00120  Primary bile acid biosynthesis
pov00120

Organism
Paralichthys olivaceus (Japanese flounder) [GN:pov]
Gene
109632307  cholesterol 24-hydroxylase [KO:K07440] [EC:1.14.14.25]
109634345  hsd3b7; 3 beta-hydroxysteroid dehydrogenase type 7 [KO:K12408] [EC:1.1.1.181]
109633719  cholesterol 25-hydroxylase-like protein [KO:K10223] [EC:1.14.99.38]
109624069  cholesterol 25-hydroxylase-like protein 1, member 1 [KO:K10223] [EC:1.14.99.38]
109624296  cholesterol 25-hydroxylase-like protein 1, member 2 [KO:K10223] [EC:1.14.99.38]
109626203  cholesterol 25-hydroxylase-like protein 2 [KO:K10223] [EC:1.14.99.38]
109646054  cholesterol 25-hydroxylase-like protein [KO:K10223] [EC:1.14.99.38]
109641444  cholesterol 7-alpha-monooxygenase [KO:K00489] [EC:1.14.14.23]
109640203  sterol 26-hydroxylase, mitochondrial-like [KO:K00488] [EC:1.14.15.15]
109641449  sterol 26-hydroxylase, mitochondrial-like [KO:K00488] [EC:1.14.15.15]
109637350  cytochrome P450 27C1 [KO:K00488] [EC:1.14.15.15]
109625444  7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase-like [KO:K07431] [EC:1.14.14.139]
109637167  7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase-like [KO:K07431] [EC:1.14.14.139]
109638123  7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase-like [KO:K07431] [EC:1.14.14.139]
109624271  LOW QUALITY PROTEIN: 3-oxo-5-beta-steroid 4-dehydrogenase-like [KO:K00251] [EC:1.3.1.3]
109632831  akr1d1; 3-oxo-5-beta-steroid 4-dehydrogenase [KO:K00251] [EC:1.3.1.3]
109626104  amacr; alpha-methylacyl-CoA racemase [KO:K01796] [EC:5.1.99.4]
109637138  hsd17b4; peroxisomal multifunctional enzyme type 2 [KO:K12405] [EC:1.1.1.- 4.2.1.107 4.2.1.119]
109646608  scp2; non-specific lipid-transfer protein [KO:K08764] [EC:2.3.1.176]
109629039  acot8; acyl-coenzyme A thioesterase 8 [KO:K11992] [EC:3.1.2.27]
109628957  bile acid-CoA:amino acid N-acyltransferase-like [KO:K00659] [EC:2.3.1.65 3.1.2.2]
109644008  bile acid-CoA:amino acid N-acyltransferase-like [KO:K00659] [EC:2.3.1.65 3.1.2.2]
Compound
C00037  Glycine
C00187  Cholesterol
C00245  Taurine
C00695  Cholic acid
C01301  3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al
C01794  Choloyl-CoA
C01921  Glycocholate
C02528  Chenodeoxycholate
C03594  7alpha-Hydroxycholesterol
C04554  3alpha,7alpha-Dihydroxy-5beta-cholestanate
C04722  3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate
C05122  Taurocholate
C05337  Chenodeoxycholoyl-CoA
C05444  3alpha,7alpha,26-Trihydroxy-5beta-cholestane
C05445  3alpha,7alpha-Dihydroxy-5beta-cholestan-26-al
C05446  3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane
C05447  (24E)-3alpha,7alpha-Dihydroxy-5beta-cholest-24-enoyl-CoA
C05448  (24R,25R)-3alpha,7alpha,24-Trihydroxy-5beta-cholestanoyl-CoA
C05449  3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA
C05451  7alpha-Hydroxy-5beta-cholestan-3-one
C05452  3alpha,7alpha-Dihydroxy-5beta-cholestane
C05453  7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one
C05454  3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane
C05455  7alpha-Hydroxycholest-4-en-3-one
C05460  (24E)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl-CoA
C05465  Taurochenodeoxycholate
C05466  Glycochenodeoxycholate
C05467  3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-CoA
C05468  5beta-Cyprinolsulfate
C06341  7alpha,27-Dihydroxycholesterol
C13550  Cerebrosterol
C15518  (24S)-Cholest-5-ene-3beta,7alpha,24-triol
C15519  25-Hydroxycholesterol
C15520  Cholest-5-ene-3beta,7alpha,25-triol
C15610  Cholest-5-ene-3beta,26-diol
C15613  (25R)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoA
C15614  (24R,25R)-3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-CoA
C17331  7alpha,24-Dihydroxy-4-cholesten-3-one
C17332  7alpha,25-Dihydroxy-4-cholesten-3-one
C17333  3beta-Hydroxy-5-cholestenoate
C17335  3beta,7alpha-Dihydroxy-5-cholestenoate
C17336  7alpha,26-Dihydroxy-4-cholesten-3-one
C17337  7alpha-Hydroxy-3-oxo-4-cholestenoate
C17339  4-Cholesten-7alpha,12alpha-diol-3-one
C17343  (25S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoA
C17345  (25R)-3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
C17346  (25S)-3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
Reference
PMID:12543708
  Authors
Russell DW
  Title
The enzymes, regulation, and genetics of bile acid synthesis.
  Journal
Annu Rev Biochem 72:137-74 (2003)
DOI:10.1146/annurev.biochem.72.121801.161712
Reference
PMID:17346171
  Authors
Norlin M, Wikvall K
  Title
Enzymes in the conversion of cholesterol into bile acids.
  Journal
Curr Mol Med 7:199-218 (2007)
DOI:10.2174/156652407780059168
Reference
PMID:10198776
  Authors
Vlahcevic ZR, Pandak WM, Stravitz RT
  Title
Regulation of bile acid biosynthesis.
  Journal
Gastroenterol Clin North Am 28:1-25, v (1999)
DOI:10.1016/S0889-8553(05)70041-8
Reference
PMID:18081658
  Authors
Pellicoro A, Faber KN
  Title
Review article: The function and regulation of proteins involved in bile salt biosynthesis and transport.
  Journal
Aliment Pharmacol Ther 26 Suppl 2:149-60 (2007)
DOI:10.1111/j.1365-2036.2007.03522.x
Reference
PMID:18488143
  Authors
Hofmann AF, Hagey LR
  Title
Bile acids: chemistry, pathochemistry, biology, pathobiology, and therapeutics.
  Journal
Cell Mol Life Sci 65:2461-83 (2008)
DOI:10.1007/s00018-008-7568-6
Reference
PMID:11067870
  Authors
Schwarz M, Wright AC, Davis DL, Nazer H, Bjorkhem I, Russell DW
  Title
The bile acid synthetic gene 3beta-hydroxy-Delta(5)-C(27)-steroid oxidoreductase is mutated in progressive intrahepatic cholestasis.
  Journal
J Clin Invest 106:1175-84 (2000)
DOI:10.1172/JCI10902
Reference
PMID:16299351
  Authors
Ridlon JM, Kang DJ, Hylemon PB
  Title
Bile salt biotransformations by human intestinal bacteria.
  Journal
J Lipid Res 47:241-59 (2006)
DOI:10.1194/jlr.R500013-JLR200
Reference
PMID:9292932
  Authors
Bortolini O, Medici A, Poli S
  Title
Biotransformations on steroid nucleus of bile acids.
  Journal
Steroids 62:564-77 (1997)
DOI:10.1016/S0039-128X(97)00043-3
Related
pathway
pov00100  Steroid biosynthesis
KO pathway
ko00120   
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