1.0 2011-09-21 00:06:30 UTC 2015-10-09 22:33:05 UTC FDB021983 3a,6a,7b-Trihydroxy-5b-cholanoic acid 3a,6a,7b-Trihydroxy-5b-cholanoic acid is an unusual trihydroxy bile acid found in the urine of healthy humans, mainly in newborns (PMID 3769218). A bile acid. 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] 3a,6a,7b-trihydroxy-5b-Cholan-24-oate 3a,6a,7b-trihydroxy-5b-Cholan-24-oic acid 3a,6a,7b-Trihydroxy-5b-cholanoate 3a,6a,7b-Trihydroxy-5b-cholanoic acid omega-Muricholate omega-Muricholic acid w-Muricholate w-Muricholic acid C24H40O5 408.5714 408.28757439 (4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid 6830-03-1 [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1 DKPMWHFRUGMUKF-NTPBNISXSA-N belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Trihydroxy bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids 6-hydroxysteroids 7-alpha-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols 3-alpha-hydroxysteroid 3-hydroxysteroid 6-hydroxysteroid 7-alpha-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Trihydroxy bile acid, alcohol, or derivatives C24 bile acids, alcohols, and derivatives bile acid Solid logp 2.16 ALOGPS logs -3.77 ALOGPS solubility 6.89e-02 g/l ALOGPS logp 2.72 ChemAxon pka_strongest_acidic 4.6 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac (4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 408.5714 ChemAxon mono_mass 408.28757439 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C ChemAxon formula C24H40O5 ChemAxon inchi InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1 ChemAxon inchikey DKPMWHFRUGMUKF-NTPBNISXSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 110.56 ChemAxon polarizability 47.1 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 1346 Specdb::NmrTwoD 1288 Specdb::CMs 23750 Specdb::CMs 37467 Specdb::CMs 156736 Specdb::CMs 1059519 Specdb::CMs 1059521 Specdb::CMs 1059523 Specdb::CMs 1059525 Specdb::CMs 1059527 Specdb::CMs 1059529 Specdb::CMs 1059531 Specdb::CMs 1059533 Specdb::CMs 1059535 Specdb::CMs 1059537 Specdb::CMs 1059539 Specdb::CMs 1059541 Specdb::CMs 1059543 Specdb::CMs 1059545 Specdb::CMs 1059546 Specdb::CMs 1059549 Specdb::CMs 1059551 Specdb::CMs 1059553 Specdb::CMs 1059555 Specdb::CMs 1059556 Specdb::CMs 1059558 Specdb::CMs 1059560 Specdb::MsMs 579 Specdb::MsMs 580 Specdb::MsMs 581 Specdb::MsMs 318652 Specdb::MsMs 318653 Specdb::MsMs 318654 Specdb::MsMs 365497 Specdb::MsMs 365498 Specdb::MsMs 365499 Specdb::MsMs 2775791 Specdb::MsMs 2775792 Specdb::MsMs 2775793 Specdb::MsMs 2905959 Specdb::MsMs 2905960 Specdb::MsMs 2905961 HMDB00364 #<Reference:0x000055ac3f18a150> #<Reference:0x000055ac3f189f98> #<Reference:0x000055ac3f189de0> #<Reference:0x000055ac3f189c28> #<Reference:0x000055ac3f189a70> 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