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
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
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
| Molecular Formula | C27H48O |
| Molecular Weight | 388.6694 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Coprostanol in Siak River sediments, E Sumatra, Indonesia. | 2010-12 |
|
| Anthropogenic organic matter inputs indicated by sedimentary fecal steroids in a large South American tropical estuary (Paranaguá estuarine system, Brazil). | 2010-11 |
|
| Sediments as a potential tool for assessment of sewage pollution in Barigüi River, Brazil. | 2010-11 |
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| Water microbiology. Bacterial pathogens and water. | 2010-10 |
|
| 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. | 2010-07-09 |
|
| Cholesterol-lowering effects of probiotics and prebiotics: a review of in vivo and in vitro findings. | 2010-06-17 |
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| Cholesterol induces specific spatial and orientational order in cholesterol/phospholipid membranes. | 2010-06-17 |
|
| Trace organic contaminants and their sources in surface sediments of Santa Monica Bay, California, USA. | 2010-06 |
|
| Determination of fecal contamination indicator sterols in an Australian water supply system. | 2010-06 |
|
| Removal of cholesterol by lactobacilli via incorporation and conversion to coprostanol. | 2010-04 |
|
| Occurrence and distribution of steroids, hormones and selected pharmaceuticals in South Florida coastal environments. | 2010-02 |
|
| Fecal steroids in riverine runoff of the Pearl River Delta, South China: levels, potential sources and inputs to the coastal ocean. | 2010-01 |
|
| Chemometric approach to validating faecal sterols as source tracer for faecal contamination in water. | 2009-12 |
|
| [Antifungal mechanism of Bacillus marinus B-9987]. | 2009-11 |
|
| PCDD/F, PBDE, and nonylphenol contamination in a semi-enclosed bay (Masan Bay, South Korea) and a Mediterranean lagoon (Thau, France). | 2009-10 |
|
| Assessment of fecal sterols in Barigui River sediments in Curitiba, Brazil. | 2009-10 |
|
| Nationwide monitoring of nonylphenolic compounds and coprostanol in sediments from Korean coastal waters. | 2009-07 |
|
| The role of cell cholesterol and the cytoskeleton in the interaction between IK1 and maxi-K channels. | 2009-04 |
|
| Determination of fecal sterols by gas chromatography-mass spectrometry with solid-phase extraction and injection-port derivatization. | 2009-02-13 |
|
| Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences. | 2009-02 |
|
| The use of FT-IR as a screening technique for organic residue analysis of archaeological samples. | 2009-02 |
|
| Evolution of the source apportionment of the lipidic fraction from sediments along the Fensch River, France: a multimolecular approach. | 2008-07-15 |
|
| Comparison of effects of dietary unesterified and esterified plant sterols on cholesterol absorption in rats. | 2008-06 |
|
| Distribution characteristics of nonylphenolic chemicals in Masan Bay environments, Korea. | 2008-04 |
|
| Body burden of contaminants and biological effects in mussels: an integrated approach. | 2008-02 |
|
| Insights into the roles of gut microbes in obesity. | 2008 |
|
| Sterols: a tracer of organic matter in combined sewers. | 2008 |
|
| Intestinal cholesterol conversion in adults and elderly from four different European countries. | 2008 |
|
| Four-week short chain fructo-oligosaccharides ingestion leads to increasing fecal bifidobacteria and cholesterol excretion in healthy elderly volunteers. | 2007-12-05 |
|
| Investigation of the solvent extracts of humic organic matter (HOM) isolated from the Ravenna Lagoon to study environmental pollution and microbial communities. | 2007-12 |
|
| 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. | 2007-11-28 |
|
| 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. | 2007-11 |
|
| Lipid biomarkers profile--presence of coprostanol: recent sediments from Rodrigo de Freitas Lagoon-Rio de Janeiro, Brazil. | 2007-09 |
|
| Evaluating potential applications of faecal sterols in distinguishing sources of faecal contamination from mixed faecal samples. | 2007-08 |
|
| Bacterial source tracking from diverse land use catchments by sterol ratios. | 2007-08 |
|
| Comparisons of water quality parameters from diverse catchments during dry periods and following rain events. | 2007-08 |
|
| Development of a method which discriminates between endogenous and exogenous beta-boldenone. | 2007-03-14 |
|
| Detection of intermittent sewage pollution in a subtropical, oligotrophic, semi-enclosed embayment system using sterol signatures in sediments. | 2007-02-01 |
|
| Application of nonylphenol and coprostanol to identification of industrial and fecal pollution in Korea. | 2007-01 |
|
| Effect of pectin and amidated pectin on cholesterol homeostasis and cecal metabolism in rats fed a high-cholesterol diet. | 2007 |
|
| Faecal sterols determination in wastewater and surface water. | 2006-10-20 |
|
| Effects of pharmaceutical products and municipal wastewaters on temperature-dependent mitochondrial electron transport activity in Elliptio complanata mussels. | 2006-08 |
|
| Sterols as bio-markers for waste impact and source characterization in stream sediment. | 2006-06 |
|
| Method validation for the simultaneous determination of fecal sterols in surface waters by gas chromatography-mass spectrometry. | 2006-02 |
|
| Gnotobiotic rats harboring human intestinal microbiota as a model for studying cholesterol-to-coprostanol conversion. | 2004-03-01 |
|
| New method for determination of fecal sterols in urine using non-chlorinated solvents. | 1998-08-25 |
|
| The occurrence of carcinoma of the rectum following ileoproctostomy for familial polyposis. | 1983-05 |
|
| Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. | 1981-03 |
|
| Ileal excretion and bacterial modification of bile acids and cholesterol in patients with continent ileostomy. | 1980-02 |
|
| Bile acid metabolism in benign recurrent intrahepatic cholestasis. Comparative studies on the icteric and anicteric phases of a single case. | 1979-05 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:55:16 GMT 2025
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| Record UNII |
PPT67I3S74
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| Record Status |
Validated (UNII)
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| Record Version |
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5060
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221122
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Coprosterol
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PPT67I3S74
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m3779
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