1.02011-09-21 00:07:14 UTC2015-07-21 06:56:56 UTCFDB0220273a,12b-Dihydroxy-5b-cholanoic acidA 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]12-epi-deoxy-Cholate12-epi-deoxy-Cholic acid12-epi-Deoxycholate12-epi-Deoxycholic acid12-Epideoxycholate12-Epideoxycholic acid3a,12b-Dihydroxy-5b-cholan-24-oate3a,12b-Dihydroxy-5b-cholan-24-oic acid3a,12b-Dihydroxy-5b-cholanate3a,12b-Dihydroxy-5b-cholanic acid3a,12b-Dihydroxy-5b-cholanoate3a,12b-Dihydroxy-5b-cholanoic acid3a,12b-Dihydroxycholanoate3a,12b-Dihydroxycholanoic acidC24H40O4392.572392.292659768(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16R)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid12-epideoxycholate570-62-7[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12CInChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21-,23+,24-/m1/s1KXGVEGMKQFWNSR-MFSKYVBHSA-N belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.Dihydroxy bile acids, alcohols and derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesBile acids, alcohols and derivativesAliphatic homopolycyclic compounds12-hydroxysteroids3-alpha-hydroxysteroidsCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesSecondary alcohols12-hydroxysteroid3-alpha-hydroxysteroid3-hydroxysteroidAlcoholAliphatic homopolycyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholDihydroxy bile acid, alcohol, or derivativesHydrocarbon derivativeHydroxysteroidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundSecondary alcoholC24 bile acids, alcohols, and derivativescholanoidSolidlogp3.30logs-4.35solubility1.73e-02 g/llogp3.79pka_strongest_acidic4.65pka_strongest_basic-0.35iupac(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16R)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acidaverage_mass392.572mono_mass392.292659768smiles[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12CformulaC24H40O4inchiInChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21-,23+,24-/m1/s1inchikeyKXGVEGMKQFWNSR-MFSKYVBHSA-Npolar_surface_area77.76refractivity109.2polarizability46.16rotatable_bond_count4acceptor_count4donor_count3physiological_charge-1formal_charge0Specdb::MsMs289753Specdb::MsMs289754Specdb::MsMs289755Specdb::MsMs329278Specdb::MsMs329279Specdb::MsMs329280Specdb::MsMs2338468Specdb::MsMs2338469Specdb::MsMs2338470Specdb::MsMs2623487Specdb::MsMs2623488Specdb::MsMs2623489Specdb::CMs10795Specdb::CMs37511Specdb::CMs134922Specdb::CMs142656Specdb::CMs1060858Specdb::CMs1060860Specdb::CMs1060862Specdb::CMs1060864Specdb::CMs1060866Specdb::CMs1060868Specdb::CMs1060870Specdb::CMs1060872Specdb::CMs1060874Specdb::CMs1060876Specdb::CMs1060878Specdb::CMs1060880Specdb::CMs1060882HMDB00411#<Reference:0x0000555673fe1298>#<Reference:0x0000555673fe10e0>#<Reference:0x0000555673fe0e60>#<Reference:0x0000555673fe0ca8>#<Reference:0x0000555673fe0aa0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823