1.02011-09-21 00:40:29 UTC2017-04-03 05:02:17 UTCFDB0241373a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA 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](24R,25R)-3-alpha,7-alpha,12-alpha,24- tetrahydroxy-5-beta-cholestanoyl-CoA(24R,25R)-3-alpha,7-alpha,12-alpha,24- tetrahydroxy-5-beta-cholestanoyl-Coenzyme A(24R,25R)-3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestanoyl-CoA(24R,25R)-3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestanoyl-coenzyme A3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-Coenzyme A3a,7a,12a,24z-Tetrahydroxy-5b-cholestanoyl-CoA3a,7a,12a,24z-Tetrahydroxy-5b-cholestanoyl-Coenzyme A3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-CoA3alpha,7alpha,12alpha,24-Tetrahydroxy-5beta-cholestanoyl-Coenzyme A3alpha,7alpha,12alpha,24zeta-Tetrahydroxy-5beta-cholestanoyl-CoA3alpha,7alpha,12alpha,24zeta-Tetrahydroxy-5beta-cholestanoyl-Coenzyme AC48H80N7O21P3S1216.1691215.434082883{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-3-[(2-{[2-({3-hydroxy-2-methyl-6-[(5R,7S,9R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-[(2-{[2-({3-hydroxy-2-methyl-6-[(5R,7S,9R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid7235-40-7[H][C@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NInChI=1S/C48H80N7O21P3S/c1-24(28-8-9-29-36-30(19-34(59)48(28,29)6)47(5)13-11-27(56)17-26(47)18-32(36)58)7-10-31(57)25(2)45(64)80-16-15-50-35(60)12-14-51-43(63)40(62)46(3,4)21-73-79(70,71)76-78(68,69)72-20-33-39(75-77(65,66)67)38(61)44(74-33)55-23-54-37-41(49)52-22-53-42(37)55/h22-34,36,38-40,44,56-59,61-62H,7-21H2,1-6H3,(H,50,60)(H,51,63)(H,68,69)(H,70,71)(H2,49,52,53)(H2,65,66,67)/t24?,25?,26-,27+,28?,29?,30?,31?,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1PXHZOQNODUPJKC-QVXJXFLKSA-N belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc.GalNAcb1-4Galb1-4Glc- (Ganglio series)Organic compoundsLipids and lipid-like moleculesSphingolipidsGlycosphingolipidsAliphatic heteromonocyclic compoundsAcetamidesAlkyl glycosidesC-glucuronidesC-glycosyl compoundsCarbonyl compoundsCarboxylic acidsGangliosidesGlycosyl-N-acylsphingosinesHydrocarbon derivativesKetalsMonocarboxylic acids and derivativesN-acyl aminesN-acyl-alpha-hexosaminesN-acylneuraminic acidsNeuraminic acidsO-glycosyl compoundsOligosaccharidesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPrimary alcoholsPyransSecondary alcoholsSecondary carboxylic acid amidesAcetalAcetamideAlcoholAliphatic heteromonocyclic compoundAlkyl glycosideC-glucuronideC-glycosyl compoundCarbonyl groupCarboxamide groupCarboxylic acidCarboxylic acid derivativeFatty acylFatty acyl glycosideFatty amideGalnacb1-4galb1-4glcb-cer_backboneGlycosyl compoundGlycosyl-n-acylsphingosineHydrocarbon derivativeKetalMonocarboxylic acid or derivativesN-acyl-alpha-hexosamineN-acyl-amineN-acylneuraminic acidN-acylneuraminic acid or derivativesNeuaca2-3galb1-4glcb-cer_backboneNeuraminic acidO-glycosyl compoundOligosaccharideOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePolyolPrimary alcoholPyranSecondary alcoholSecondary carboxylic acid amideSolidlogp0.65logs-3.01solubility1.18e+00 g/llogp-4.1pka_strongest_acidic0.83pka_strongest_basic4.95iupac{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-3-[(2-{[2-({3-hydroxy-2-methyl-6-[(5R,7S,9R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acidaverage_mass1216.169mono_mass1215.434082883smiles[H][C@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NformulaC48H80N7O21P3SinchiInChI=1S/C48H80N7O21P3S/c1-24(28-8-9-29-36-30(19-34(59)48(28,29)6)47(5)13-11-27(56)17-26(47)18-32(36)58)7-10-31(57)25(2)45(64)80-16-15-50-35(60)12-14-51-43(63)40(62)46(3,4)21-73-79(70,71)76-78(68,69)72-20-33-39(75-77(65,66)67)38(61)44(74-33)55-23-54-37-41(49)52-22-53-42(37)55/h22-34,36,38-40,44,56-59,61-62H,7-21H2,1-6H3,(H,50,60)(H,51,63)(H,68,69)(H,70,71)(H2,49,52,53)(H2,65,66,67)/t24?,25?,26-,27+,28?,29?,30?,31?,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1inchikeyPXHZOQNODUPJKC-QVXJXFLKSA-Npolar_surface_area444.55refractivity285.65polarizability119.66rotatable_bond_count26acceptor_count21donor_count13physiological_charge-4formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::NmrOneD91992Specdb::NmrOneD91993Specdb::NmrOneD91994Specdb::NmrOneD91995Specdb::NmrOneD91996Specdb::NmrOneD91997Specdb::NmrOneD91998Specdb::NmrOneD91999Specdb::NmrOneD92000Specdb::NmrOneD92001Specdb::NmrOneD92002Specdb::NmrOneD92003Specdb::NmrOneD92004Specdb::NmrOneD92005Specdb::NmrOneD92006Specdb::NmrOneD92007Specdb::NmrOneD92008Specdb::NmrOneD92009Specdb::NmrOneD92010Specdb::NmrOneD92011Specdb::MsMs312820Specdb::MsMs312821Specdb::MsMs312822Specdb::MsMs358165Specdb::MsMs358166Specdb::MsMs358167Specdb::MsMs2736383Specdb::MsMs2736384Specdb::MsMs2736385Specdb::MsMs2969019Specdb::MsMs2969020Specdb::MsMs2969021HMDB0689027458#<Reference:0x0000555675f82c78>#<Reference:0x0000555675f82ac0>#<Reference:0x0000555675f82908>#<Reference:0x0000555675f82700>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 scrofa9823Retinol dehydrogenase 13Q8NBN7RDH13