1.0 2011-09-21 00:08:51 UTC 2018-05-29 01:52:44 UTC FDB022125 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 . 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. [HMDB] (3b,5b)-cholestan-3-ol 3b-Hydroxy-5b-cholestanol 5b-Cholestan-3b-ol 5b-Coprostanol 5beta Coprostanol 5beta-cholestan-3beta-ol 5beta-Coprostanol Stercorin C27H48O 388.6694 388.370516158 (1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol (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 360-68-9 [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 QYIXCDOBOSTCEI-NWKZBHTNSA-N belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cholestane steroids Aliphatic homopolycyclic compounds 3-beta-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols 3-beta-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cholesterol Cholesterol-skeleton Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Cholesterol and derivatives Solid logp 7.02 ALOGPS logs -7.41 ALOGPS solubility 1.51e-05 g/l ALOGPS logp 7.52 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (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 ChemAxon average_mass 388.6694 ChemAxon mono_mass 388.370516158 ChemAxon 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 ChemAxon formula C27H48O ChemAxon inchi 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 ChemAxon inchikey QYIXCDOBOSTCEI-NWKZBHTNSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 119.77 ChemAxon polarizability 50.82 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1374 Specdb::MsMs 6246 Specdb::MsMs 295168 Specdb::MsMs 295169 Specdb::MsMs 295170 Specdb::MsMs 336103 Specdb::MsMs 336104 Specdb::MsMs 336105 Specdb::MsMs 2791691 Specdb::MsMs 2791692 Specdb::MsMs 2791693 Specdb::MsMs 2916785 Specdb::MsMs 2916786 Specdb::MsMs 2916787 Specdb::CMs 13263 Specdb::CMs 27513 Specdb::CMs 37635 Specdb::CMs 99585 Specdb::CMs 165527 Specdb::CMs 1066919 Specdb::NmrOneD 1429 Specdb::NmrOneD 291935 Specdb::NmrOneD 291936 Specdb::NmrOneD 291937 Specdb::NmrOneD 291938 Specdb::NmrOneD 291939 Specdb::NmrOneD 291940 Specdb::NmrOneD 291941 Specdb::NmrOneD 291942 Specdb::NmrOneD 291943 Specdb::NmrOneD 291944 Specdb::NmrOneD 291945 Specdb::NmrOneD 291946 Specdb::NmrOneD 291947 Specdb::NmrOneD 291948 Specdb::NmrOneD 291949 Specdb::NmrOneD 291950 Specdb::NmrOneD 291951 Specdb::NmrOneD 291952 Specdb::NmrOneD 291953 Specdb::NmrOneD 291954 HMDB00577 #<Reference:0x000055ce318d9c58> #<Reference:0x000055ce318d9aa0> #<Reference:0x000055ce318d98e8> #<Reference:0x000055ce318d9730> #<Reference:0x000055ce318d9578> #<Reference:0x000055ce318d93c0> #<Reference:0x000055ce318d9208> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823