1.02011-09-21 00:40:33 UTC2015-07-21 06:58:00 UTCFDB0241433a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA is an intermediate involved in the synthesis of Chenodeoxyglycocholoyl-CoA, which is is a coenzyme A derivative of chenodeoxyglycocholate. It is involved in bile acid synthesis and is the second-to-last component in the synthesis of chenodeoxyglycocholate. 3a,7a-dihydroxy-5b-24-oxocholestanoyl-CoA is synthesized from 3a,7a,24-trihydroxy-5b-cholestanoyl-CoA and then transformed via acetyl-coA acyltransferase to chenodeoxyglycocholoyl-CoA and then finally to chenodeoxyglycocholate. Chenodeoxyglycocholate is a glycine conjugated 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,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA3a,7a-Dihydroxy-5b-24-oxocholestanoyl-Coenzyme A3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-Coenzyme AC48H78N7O20P3S1198.1541197.423518197{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methyl-3-oxoheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methyl-3-oxoheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(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/C48H78N7O20P3S/c1-25(29-8-9-30-36-31(12-15-48(29,30)6)47(5)14-11-28(56)19-27(47)20-33(36)58)7-10-32(57)26(2)45(63)79-18-17-50-35(59)13-16-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-34-39(74-76(64,65)66)38(60)44(73-34)55-24-54-37-41(49)52-23-53-42(37)55/h23-31,33-34,36,38-40,44,56,58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25?,26?,27-,28+,29?,30?,31?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1QWTJBRPOHKIMDT-XWFLEUKDSA-N belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.3-oxo-acyl CoAsOrganic compoundsLipids and lipid-like moleculesFatty AcylsFatty acyl thioestersAromatic heteropolycyclic compounds1,3-dicarbonyl compounds2,3,4-saturated fatty acyl CoAs3-alpha-hydroxysteroids6-aminopurines7-hydroxysteroidsAminopyrimidines and derivativesAzacyclic compoundsBeta amino acids and derivativesCarbothioic S-estersCoenzyme A and derivativesCyclic alcohols and derivativesDihydroxy bile acids, alcohols and derivativesGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesImidolactamsKetonesMedium-chain fatty acyl CoAsMonoalkyl phosphatesMonosaccharide phosphatesN-acyl aminesN-substituted imidazolesOrganic oxidesOrganic pyrophosphatesOrganopnictogen compoundsOxacyclic compoundsOxosteroidsPentose phosphatesPrimary aminesPurine ribonucleoside diphosphatesRibonucleoside 3'-phosphatesSecondary alcoholsSecondary carboxylic acid amidesSteroidal glycosidesSulfenyl compoundsTetrahydrofuransThioesters1,3-dicarbonyl compound24-oxosteroid3-alpha-hydroxysteroid3-hydroxysteroid6-aminopurine7-hydroxysteroidAlcoholAlkyl phosphateAmineAmino acid or derivativesAminopyrimidineAromatic heteropolycyclic compoundAzacycleAzoleBeta amino acid or derivativesBile acid, alcohol, or derivativesCarbonyl groupCarbothioic s-esterCarboxamide groupCarboxylic acid derivativeCholane-skeletonCoenzyme a or derivativesCyclic alcoholDihydroxy bile acid, alcohol, or derivativesFatty amideGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeHydroxy bile acid, alcohol, or derivativesHydroxysteroidImidazoleImidazopyrimidineImidolactamKetoneMonoalkyl phosphateMonosaccharideMonosaccharide phosphateN-acyl-amineN-glycosyl compoundN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic pyrophosphateOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOrganosulfur compoundOxacycleOxosteroidPentose monosaccharidePentose phosphatePentose-5-phosphatePhosphoric acid esterPrimary aminePurinePurine ribonucleoside 3',5'-bisphosphatePurine ribonucleoside bisphosphatePurine ribonucleoside diphosphatePyrimidineRibonucleoside 3'-phosphateSecondary alcoholSecondary carboxylic acid amideSteroidSteroidal glycosideSulfenyl compoundTetrahydrofuranThiocarboxylic acid esterThiocarboxylic acid or derivativesSolidlogp1.48logs-3.17solubility8.04e-01 g/llogp-2.3pka_strongest_acidic0.83pka_strongest_basic4.95iupac{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methyl-3-oxoheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acidaverage_mass1198.154mono_mass1197.423518197smiles[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(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=C2NformulaC48H78N7O20P3SinchiInChI=1S/C48H78N7O20P3S/c1-25(29-8-9-30-36-31(12-15-48(29,30)6)47(5)14-11-28(56)19-27(47)20-33(36)58)7-10-32(57)26(2)45(63)79-18-17-50-35(59)13-16-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-34-39(74-76(64,65)66)38(60)44(73-34)55-24-54-37-41(49)52-23-53-42(37)55/h23-31,33-34,36,38-40,44,56,58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25?,26?,27-,28+,29?,30?,31?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1inchikeyQWTJBRPOHKIMDT-XWFLEUKDSA-Npolar_surface_area421.16refractivity283.31polarizability118.54rotatable_bond_count26acceptor_count20donor_count11physiological_charge-4formal_charge0Specdb::NmrOneD92052Specdb::NmrOneD92053Specdb::NmrOneD92054Specdb::NmrOneD92055Specdb::NmrOneD92056Specdb::NmrOneD92057Specdb::NmrOneD92058Specdb::NmrOneD92059Specdb::NmrOneD92060Specdb::NmrOneD92061Specdb::NmrOneD92062Specdb::NmrOneD92063Specdb::NmrOneD92064Specdb::NmrOneD92065Specdb::NmrOneD92066Specdb::NmrOneD92067Specdb::NmrOneD92068Specdb::NmrOneD92069Specdb::NmrOneD92070Specdb::NmrOneD92071Specdb::MsMs317146Specdb::MsMs317147Specdb::MsMs317148Specdb::MsMs363550Specdb::MsMs363551Specdb::MsMs363552Specdb::MsMs2466431Specdb::MsMs2466432Specdb::MsMs2466433Specdb::MsMs2496104Specdb::MsMs2496105Specdb::MsMs2496106HMDB0689628533#<Reference:0x0000555675ed48f8>#<Reference:0x0000555675ed4740>#<Reference:0x0000555675ed4588>#<Reference:0x0000555675ed43d0>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 scrofa98233-ketoacyl-CoA thiolase, peroxisomalP09110ACAA1Non-specific lipid-transfer proteinP22307SCP2Trifunctional enzyme subunit beta, mitochondrialP55084HADHB