Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H48O |
| Molecular Weight | 388.6694 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=QYIXCDOBOSTCEI-NWKZBHTNSA-N
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
Coprosterol (also known as a coprostanol) is a byproduct of cholesterol found in human feces. It was shown, that microbiota-mediated transformation of fecal cholesterol to coprostanol may enhance resistance to C. difficile infection. This can be achieved by altering toxin entry and decreasing the availability of cholesterol substrates for primary bile acids generation. Clostridium difficile infection is characterized by dysbiosis of the intestinal microbiota and a profound derangement in the fecal metabolome. It has been suggested that a high efficiency of cholesterol to coprostanol metabolism may reduce the risk of cardiovascular disease and low rates of cholesterol to coprostanol conversion have been implicated in the progression of ulcerative colitis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Bile acid metabolism in benign recurrent intrahepatic cholestasis. Comparative studies on the icteric and anicteric phases of a single case. | 1979 May |
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| Ileal excretion and bacterial modification of bile acids and cholesterol in patients with continent ileostomy. | 1980 Feb |
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| Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. | 1981 Mar |
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| The occurrence of carcinoma of the rectum following ileoproctostomy for familial polyposis. | 1983 May |
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| New method for determination of fecal sterols in urine using non-chlorinated solvents. | 1998 Aug 25 |
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| Gnotobiotic rats harboring human intestinal microbiota as a model for studying cholesterol-to-coprostanol conversion. | 2004 Mar 1 |
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| Tracing anthropogenic contamination in the Pearl River estuarine and marine environment of South China Sea using sterols and other organic molecular markers. | 2005 Aug |
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| Sterols and anionic surfactants in urban aerosol: emissions from wastewater treatment plants in relation to background concentrations. | 2005 Jun 15 |
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| Impact of membrane cholesterol content on the resistance of vesicles to surfactant attack. | 2005 Oct 25 |
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| Method validation for the simultaneous determination of fecal sterols in surface waters by gas chromatography-mass spectrometry. | 2006 Feb |
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| First synthesis of free cholesterol-BODIPY conjugates. | 2006 Feb 17 |
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| Effects of selected pharmaceutical products on phagocytic activity in Elliptio complanata mussels. | 2006 Jun |
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| An efficient diethyl ether-based soxhlet protocol to quantify faecal sterols from catchment waters. | 2006 Mar 3 |
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| Phase behavior of lipid monolayers containing DPPC and cholesterol analogs. | 2006 May 1 |
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| Evaluating potential applications of faecal sterols in distinguishing sources of faecal contamination from mixed faecal samples. | 2007 Aug |
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| Bacterial source tracking from diverse land use catchments by sterol ratios. | 2007 Aug |
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| Investigation of the solvent extracts of humic organic matter (HOM) isolated from the Ravenna Lagoon to study environmental pollution and microbial communities. | 2007 Dec |
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| Four-week short chain fructo-oligosaccharides ingestion leads to increasing fecal bifidobacteria and cholesterol excretion in healthy elderly volunteers. | 2007 Dec 5 |
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| Application of nonylphenol and coprostanol to identification of industrial and fecal pollution in Korea. | 2007 Jan |
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| Use of selected chemical markers in combination with a multiple regression model to assess the contribution of domesticated animal sources of fecal pollution in the environment. | 2007 Nov |
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| Simultaneous characterization of bile acid, sterols, and determination of acylglycerides in feces from soluble cellulose-fed hamsters using HPLC with evaporative light-scattering detection and APCI-MS. | 2007 Nov 28 |
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| Lipid biomarkers profile--presence of coprostanol: recent sediments from Rodrigo de Freitas Lagoon-Rio de Janeiro, Brazil. | 2007 Sep |
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| Insights into the roles of gut microbes in obesity. | 2008 |
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| Sterols: a tracer of organic matter in combined sewers. | 2008 |
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| Intestinal cholesterol conversion in adults and elderly from four different European countries. | 2008 |
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| Distribution characteristics of nonylphenolic chemicals in Masan Bay environments, Korea. | 2008 Apr |
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| Body burden of contaminants and biological effects in mussels: an integrated approach. | 2008 Feb |
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| Evolution of the source apportionment of the lipidic fraction from sediments along the Fensch River, France: a multimolecular approach. | 2008 Jul 15 |
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| Comparison of effects of dietary unesterified and esterified plant sterols on cholesterol absorption in rats. | 2008 Jun |
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| The role of cell cholesterol and the cytoskeleton in the interaction between IK1 and maxi-K channels. | 2009 Apr |
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| Chemometric approach to validating faecal sterols as source tracer for faecal contamination in water. | 2009 Dec |
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| Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences. | 2009 Feb |
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| The use of FT-IR as a screening technique for organic residue analysis of archaeological samples. | 2009 Feb |
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| Determination of fecal sterols by gas chromatography-mass spectrometry with solid-phase extraction and injection-port derivatization. | 2009 Feb 13 |
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| Nationwide monitoring of nonylphenolic compounds and coprostanol in sediments from Korean coastal waters. | 2009 Jul |
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| [Antifungal mechanism of Bacillus marinus B-9987]. | 2009 Nov |
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| PCDD/F, PBDE, and nonylphenol contamination in a semi-enclosed bay (Masan Bay, South Korea) and a Mediterranean lagoon (Thau, France). | 2009 Oct |
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| Assessment of fecal sterols in Barigui River sediments in Curitiba, Brazil. | 2009 Oct |
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| Removal of cholesterol by lactobacilli via incorporation and conversion to coprostanol. | 2010 Apr |
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| Coprostanol in Siak River sediments, E Sumatra, Indonesia. | 2010 Dec |
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| Occurrence and distribution of steroids, hormones and selected pharmaceuticals in South Florida coastal environments. | 2010 Feb |
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| Fecal steroids in riverine runoff of the Pearl River Delta, South China: levels, potential sources and inputs to the coastal ocean. | 2010 Jan |
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| Improving analysis of apolar organic compounds by the use of a capillary titania-based column: Application to the direct determination of faecal sterols cholesterol and coprostanol in wastewater samples. | 2010 Jul 9 |
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| Trace organic contaminants and their sources in surface sediments of Santa Monica Bay, California, USA. | 2010 Jun |
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| Determination of fecal contamination indicator sterols in an Australian water supply system. | 2010 Jun |
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| Cholesterol-lowering effects of probiotics and prebiotics: a review of in vivo and in vitro findings. | 2010 Jun 17 |
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| Cholesterol induces specific spatial and orientational order in cholesterol/phospholipid membranes. | 2010 Jun 17 |
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| Anthropogenic organic matter inputs indicated by sedimentary fecal steroids in a large South American tropical estuary (Paranaguá estuarine system, Brazil). | 2010 Nov |
|
| Sediments as a potential tool for assessment of sewage pollution in Barigüi River, Brazil. | 2010 Nov |
|
| Water microbiology. Bacterial pathogens and water. | 2010 Oct |
Patents
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18175
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5060
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221122
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Coprosterol
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PPT67I3S74
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DTXSID1052036
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89519
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206-638-8
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m3779
Created by
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360-68-9
Created by
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SUBSTANCE RECORD
