1.0 2011-09-21 00:40:30 UTC 2015-07-21 06:58:00 UTC FDB024139 7a-Hydroxy-5b-cholestan-3-one 7alpha-Hydroxy-5beta-cholestan-3-one is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB] 5b-cholestan-7a-ol-3-one 5beta-cholestan-7alpha-ol-3-one 7a-Hydroxy-5b-cholestan-3-one 7alpha-Hydroxy-5beta-cholestan-3-one C27H46O2 402.6529 402.349780716 (2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one (2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h17-19,21-25,29H,6-16H2,1-5H3/t18?,19?,21?,22?,23?,24-,25?,26-,27+/m0/s1 HWOOALPDOJHOPO-SENDYOAPSA-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-oxosteroids 7-alpha-hydroxysteroids Cyclic alcohols and derivatives Cyclic ketones Hydrocarbon derivatives Organic oxides Secondary alcohols 3-oxosteroid 7-alpha-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cholesterol-skeleton Cyclic alcohol Cyclic ketone Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Solid logp 5.53 ALOGPS logs -6.66 ALOGPS solubility 8.77e-05 g/l ALOGPS logp 6.42 ChemAxon pka_strongest_acidic 19.99 ChemAxon pka_strongest_basic -0.58 ChemAxon iupac (2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one ChemAxon average_mass 402.6529 ChemAxon mono_mass 402.349780716 ChemAxon smiles CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C ChemAxon formula C27H46O2 ChemAxon inchi InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h17-19,21-25,29H,6-16H2,1-5H3/t18?,19?,21?,22?,23?,24-,25?,26-,27+/m0/s1 ChemAxon inchikey HWOOALPDOJHOPO-SENDYOAPSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 120.33 ChemAxon polarizability 50.43 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 12799 Specdb::CMs 39133 Specdb::CMs 137752 Specdb::CMs 145486 Specdb::MsMs 294106 Specdb::MsMs 294107 Specdb::MsMs 294108 Specdb::MsMs 334744 Specdb::MsMs 334745 Specdb::MsMs 334746 Specdb::MsMs 2782168 Specdb::MsMs 2782169 Specdb::MsMs 2782170 Specdb::MsMs 2927524 Specdb::MsMs 2927525 Specdb::MsMs 2927526 HMDB06892 2290 #<Reference:0x00005612730908e0> #<Reference:0x00005612730906d8> #<Reference:0x00005612730903b8> #<Reference:0x00005612730900e8> 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 3-oxo-5-beta-steroid 4-dehydrogenase P51857 AKR1D1