Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:00 UTC |
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HMDB ID | HMDB0000308 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3b-Hydroxy-5-cholenoic acid |
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Description | 3b-Hydroxy-5-cholenoic acid, also known as 3b-hydroxy-chol-5-en-24-oate or cholenate, belongs to the class of organic compounds known as monohydroxy bile acids. These are bile acids bearing a hydroxyl group. Bile acids facilitate fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). When present in sufficiently high levels, bile acids can act as hepatotoxins and metabotoxisn. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. |
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Structure | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1 |
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Synonyms | Value | Source |
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3b-Hydroxy-5-cholenoate | Generator | 3b-Hydroxy-chol-5-en-24-Oate | HMDB | 3b-Hydroxy-chol-5-en-24-Oic acid | HMDB | 3b-Hydroxychol-5-en-24-ate | HMDB | 3b-Hydroxychol-5-en-24-ic acid | HMDB | 3b-Hydroxychol-5-en-24-Oate | HMDB | 3b-Hydroxychol-5-en-24-Oic acid | HMDB | 3b-Hydroxychol-5-enoate | HMDB | 3b-Hydroxychol-5-enoic acid | HMDB | 3b-Hydroxycholenoate | HMDB | 3b-Hydroxycholenoic acid | HMDB | 3beta-Hydroxy-5-cholenic acid | HMDB | 3beta-Hydroxy-5-cholenoate | HMDB | 3beta-Hydroxy-5-cholenoic acid | HMDB | 3beta-Hydroxy-chol-5-en-24-Oate | HMDB | 3beta-Hydroxy-chol-5-en-24-Oic acid | HMDB | 3beta-Hydroxy-delta5-cholenic acid | HMDB, MeSH | 3beta-Hydroxychol-5-en-24-Oate | HMDB | 3beta-Hydroxychol-5-en-24-Oic acid | HMDB | Cholenate | HMDB | Cholenic acid | HMDB | D5-Cholenate | HMDB | D5-Cholenic acid | HMDB | 3 beta-Hydroxy-5-cholenic acid | MeSH, HMDB | 3 beta-Hydroxy-delta 5-cholenic acid, sodium salt | MeSH, HMDB | 3 beta-Hydroxy-delta 5-cholenic acid | MeSH, HMDB | 3 beta-Hydroxy-5-cholenoic acid | MeSH, HMDB | (4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]pentanoate | Generator, HMDB |
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Chemical Formula | C24H38O3 |
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Average Molecular Weight | 374.5567 |
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Monoisotopic Molecular Weight | 374.282095082 |
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IUPAC Name | (4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid |
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Traditional Name | (4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid |
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CAS Registry Number | 5255-17-4 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1 |
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InChI Key | HIAJCGFYHIANNA-QIZZZRFXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Bile acids, alcohols and derivatives |
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Direct Parent | Monohydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Monohydroxy bile acid, alcohol, or derivatives
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organic oxide
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3b-Hydroxy-5-cholenoic acid,1TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3203.3 | Semi standard non polar | 33892256 | 3b-Hydroxy-5-cholenoic acid,1TMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3311.6 | Semi standard non polar | 33892256 | 3b-Hydroxy-5-cholenoic acid,2TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3248.2 | Semi standard non polar | 33892256 | 3b-Hydroxy-5-cholenoic acid,1TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3488.0 | Semi standard non polar | 33892256 | 3b-Hydroxy-5-cholenoic acid,1TBDMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3537.2 | Semi standard non polar | 33892256 | 3b-Hydroxy-5-cholenoic acid,2TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3770.1 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ktb-0119000000-d9c374e9f5f5293a5dca | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-0udi-2115890000-77f8ec28775146b3a80a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0a4j-9538000000-967e828abd3f3d7ea705 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-00kf-9800000000-fd3b7c3599b83e132518 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0w29-1695000000-3a7e6bdffc7807847034 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Positive-QTOF | splash10-0a4i-0009000000-d81080951979776b8851 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Positive-QTOF | splash10-0bvr-0029000000-57d452e5f3215053dec5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Positive-QTOF | splash10-052b-2296000000-bc9371e40f0a8181ee48 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Negative-QTOF | splash10-00di-0009000000-5f1cbb9d5b0d94fca8ae | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Negative-QTOF | splash10-0ab9-0009000000-81084972d3f11745deaa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Negative-QTOF | splash10-0a4l-9006000000-cc93a4f9f513c8d5c003 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Negative-QTOF | splash10-00di-0009000000-666fef074d788c106dcb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Negative-QTOF | splash10-05fr-0009000000-7995f4531885f9d2edf6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Negative-QTOF | splash10-0a4i-4059000000-4a851016b0c31ca828ca | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Positive-QTOF | splash10-056r-0009000000-589eec7541e9d9499e9a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Positive-QTOF | splash10-0a4s-3298000000-26204184430e4b9552c8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Positive-QTOF | splash10-0a4i-3941000000-109ac8dcc89c0c4c8858 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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General References | - Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
- Vanderpas JB, Koopman BJ, Cadranel S, Vandenbergen C, Rickaert F, Quenon M, Wolthers BG, Brauherz G, Vertongen F, Tondeur M: Malabsorption of liposoluble vitamins in a child with bile acid deficiency. J Pediatr Gastroenterol Nutr. 1987 Jan-Feb;6(1):33-41. [PubMed:3794931 ]
- St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
- Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
- Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
- Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
- Norman A, Strandvik B: Formation and metabolism of bile acids in extrahepatic biliary atresia. J Lab Clin Med. 1971 Aug;78(2):181-93. [PubMed:5567561 ]
- Hernanz A, Codoceo R, Jara P, Diaz C: Unusual serum bile acid pattern in children with the syndrome of hepatic ductular hypoplasia. Clin Chim Acta. 1985 Feb 15;145(3):289-96. [PubMed:3987031 ]
- Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. [PubMed:1641875 ]
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