5beta-Coprostanol
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.
Structure for HMDB00577 (5beta-Coprostanol)
C27H48O
388.6694
388.370516158
(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
coprostanol
360-68-9
QYIXCDOBOSTCEI-NWKZBHTNSA-N
Not classified
Detected but not Quantified
Solid
LC-MS/MS Spectrum – EI-B (JEOL JMS-01-SG-2) , Positivesplash10-052u-9527000000-d23f4273340e8c85dc8aView in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
Normal
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB022125
Not Available
191826
Not Available
Not Available
Not Available
Coprosterol
HMDB00577
HMDB00577
5559
221122
Not Available
Not Available
- 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 ]