Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:04 UTC |
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HMDB ID | HMDB0000577 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5beta-Coprostanol |
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Description | Coprosterol or coprostanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Coprosterol is the odorous principle of feces. It is formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment. American physician Austin Flint named it stercorin (Wikipedia ). The transformation of cholesterol into coprosterol in its passage through the body involves a reduction of the C5:C6 double bond, and a transition from the allocholanic- to the cholanic-ring system. Although it is established that the bacterial flora of the intestine is concerned in the reduction process, the mechanism by which the stereochemical change is brought about is unknown. Current data suggests that cholestenone and coprostanone, and not cholesterol itself, are the immediate precursors of coprosterol which is formed from them in the intestine by bacterial reduction. Coprosterol is also a microbial metabolite, it can be produced by Lactobacillus (PMID: 20338415 ). |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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(3beta,5beta)-Cholestan-3-ol | ChEBI | 5beta Coprostanol | ChEBI | 5beta-Cholestan-3beta-ol | ChEBI | Coprosterol | ChEBI | (3b,5b)-Cholestan-3-ol | Generator | (3Β,5β)-cholestan-3-ol | Generator | 5b Coprostanol | Generator | 5Β coprostanol | Generator | 5b-Cholestan-3b-ol | Generator | 5Β-cholestan-3β-ol | Generator | 5b-Coprostanol | Generator | 5Β-coprostanol | Generator | 3b-Hydroxy-5b-cholestanol | HMDB | Stercorin | HMDB | 5 beta-Cholestan-3 beta-ol | HMDB | 5 alpha Cholestan 3 alpha ol | HMDB | Coprostanol | HMDB | 5 beta-Cholestan-3 alpha-ol | HMDB | Cholestan 3 ol | HMDB | Cholestanol, (3alpha, 5beta)-isomer | HMDB | beta-Cholestanol | HMDB | beta-Cholestan-3 beta-ol, 5 | HMDB | Cholestan-3-ol | HMDB | Cholestanol | HMDB | Dihydrocholesterol | HMDB | beta-Ol, 5 beta-cholestan-3 | HMDB | 5 alpha Cholestan 3 beta ol | HMDB | beta Cholestanol | HMDB | 5 alpha-Cholestan-3 alpha-ol | HMDB | 5 alpha-Cholestan-3 beta-ol | HMDB | 5 beta Cholestan 3 beta ol | HMDB |
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Chemical Formula | C27H48O |
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Average Molecular Weight | 388.6694 |
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Monoisotopic Molecular Weight | 388.370516158 |
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IUPAC Name | (1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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Traditional Name | (1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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CAS Registry Number | 360-68-9 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
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InChI Identifier | InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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InChI Key | QYIXCDOBOSTCEI-NWKZBHTNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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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 | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol-skeleton
- Cholesterol
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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 | |
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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 | 102 °C | 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 5beta-Coprostanol EI-B (Non-derivatized) | splash10-052u-9527000000-d23f4273340e8c85dc8a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 5beta-Coprostanol EI-B (Non-derivatized) | splash10-052u-9527000000-d23f4273340e8c85dc8a | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (Non-derivatized) - 70eV, Positive | splash10-05i0-0109000000-761dcf3fe040f44fa80e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (1 TMS) - 70eV, Positive | splash10-0002-3104900000-654dcbe9dd07b5a589f2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (TBDMS_1_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 - 5beta-Coprostanol EI-B (JEOL JMS-01-SG-2) , Positive-QTOF | splash10-052u-9527000000-d23f4273340e8c85dc8a | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Positive-QTOF | splash10-0079-0009000000-57023400d5e478a8c746 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Positive-QTOF | splash10-00dr-3039000000-9ce6c0a362b9f376d3f0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Positive-QTOF | splash10-0ab9-4159000000-32959ebb75235db63ac3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Negative-QTOF | splash10-000i-0009000000-134a888410f8beddca3b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Negative-QTOF | splash10-000i-0009000000-c42f43f5e21141f5a909 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Negative-QTOF | splash10-0ab9-1009000000-8096d56c7bfdd221f9c2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Negative-QTOF | splash10-000i-0009000000-34ef429285e58bb4b314 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Negative-QTOF | splash10-000i-0009000000-780ac33d63315f658159 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Negative-QTOF | splash10-000i-0009000000-2b8e0e9916832dc47876 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Positive-QTOF | splash10-000i-0009000000-44afea742dee80d0734e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Positive-QTOF | splash10-0a4i-9032000000-166905331dad000292e6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Positive-QTOF | splash10-0a4j-9820000000-f066461902c4fe39e2d4 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn disease | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
| Ulcerative colitis |
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- Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
| Crohn's disease |
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- Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022125 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 191826 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Coprosterol |
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METLIN ID | 5559 |
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PubChem Compound | 221122 |
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PDB ID | Not Available |
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ChEBI ID | 89519 |
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Food Biomarker Ontology | Not Available |
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VMH ID | COPROST |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Lieber, Iris Ilona. Metabolism of cholesterol. New theory of the formation of coprosterol. Prensa Medica Argentina (1960), 47 3097-3100. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Borjesson E, Sundin A, Leeming R, Torstensson L: New method for determination of fecal sterols in urine using non-chlorinated solvents. J Chromatogr B Biomed Sci Appl. 1998 Aug 25;713(2):438-42. [PubMed:9746261 ]
- Kay RM, Cohen Z, Siu KP, Petrunka CN, Strasberg SM: Ileal excretion and bacterial modification of bile acids and cholesterol in patients with continent ileostomy. Gut. 1980 Feb;21(2):128-32. [PubMed:7380334 ]
- Watne AL, Carrier JM, Durham JP, Hrabovsky EE, Chang W: The occurrence of carcinoma of the rectum following ileoproctostomy for familial polyposis. Ann Surg. 1983 May;197(5):550-4. [PubMed:6847274 ]
- Schonning C, Leeming R, Stenstrom TA: Faecal contamination of source-separated human urine based on the content of faecal sterols. Water Res. 2002 Apr;36(8):1965-72. [PubMed:12092571 ]
- McNamara DJ, Proia A, Miettinen TA: Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. J Lipid Res. 1981 Mar;22(3):474-84. [PubMed:7240972 ]
- Endo T, Uchida K, Amuro Y, Higashino K, Yamamura Y: Bile acid metabolism in benign recurrent intrahepatic cholestasis. Comparative studies on the icteric and anicteric phases of a single case. Gastroenterology. 1979 May;76(5 Pt 1):1002-6. [PubMed:437403 ]
- Veiga P, Juste C, Lepercq P, Saunier K, Beguet F, Gerard P: Correlation between faecal microbial community structure and cholesterol-to-coprostanol conversion in the human gut. FEMS Microbiol Lett. 2005 Jan 1;242(1):81-6. [PubMed:15621423 ]
- Lye HS, Rusul G, Liong MT: Removal of cholesterol by lactobacilli via incorporation and conversion to coprostanol. J Dairy Sci. 2010 Apr;93(4):1383-92. doi: 10.3168/jds.2009-2574. [PubMed:20338415 ]
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