1.0 2011-09-21 00:40:29 UTC 2015-07-21 06:58:00 UTC FDB024138 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA 3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-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-cholestan-26-oyl-CoA (24R,25R)-3-alpha,7-alpha,12-alpha,24-tetrahydroxy-5-beta-cholestan-26-oyl-Coenzyme A 24-oxo-25(R)-trihydroxycoprostanoyl-CoA 24-oxo-25(R)-trihydroxycoprostanoyl-Coenzyme A 25(R)-24-oxo-3alpha,7alpha,12alpha-trihydroxycoprostanoyl-CoA 25(R)-24-oxo-3alpha,7alpha,12alpha-trihydroxycoprostanoyl-Coenzyme A 25(R)-3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestanoyl-CoA 25(R)-3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestanoyl-Coenzyme A 25(R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-24-on-26-oyl-CoA 25(R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-24-on-26-oyl-Coenzyme A 25(R)-5beta-cholestane-3alpha,7alpha,12alpha-triol-24-on-26-oyl-CoA 25(R)-5beta-cholestane-3alpha,7alpha,12alpha-triol-24-on-26-oyl-Coenzyme A 3-alpha,7-alpha,12-alpha-trihydroxy-24-oxo-5-beta-cholestanoyl-CoA 3-alpha,7-alpha,12-alpha-trihydroxy-24-oxo-5-beta-cholestanoyl-Coenzyme A 3-alpha,7-alpha,12-alpha,24-tetrahydroxy-5-beta-cholestan-26-oyl-CoA 3-alpha,7-alpha,12-alpha,24-tetrahydroxy-5-beta-cholestan-26-oyl-Coenzyme A 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-Coenzyme A 3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-CoA 3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-Coenzyme A 3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-CoA 3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-Coenzyme A R-TrHOCCoA R-TrHOCCoenzyme A C48H78N7O21P3S 1214.154 1213.418432819 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({2-methyl-3-oxo-6-[(1S,5R,7S,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})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-2,2-dimethyl-3-[(2-{[2-({2-methyl-3-oxo-6-[(1S,5R,7S,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid [H][C@@]12CCC(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]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)C[C@]2([H])C[C@H](O)CCC12C InChI=1S/C48H78N7O21P3S/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/h22-30,32-34,36,38-40,44,56,58-59,61-62H,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-,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1 AWLXQJGPNLCTLM-XFQWJXLTSA-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 CoAs Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl thioesters Aromatic heteropolycyclic compounds 1,3-dicarbonyl compounds 12-hydroxysteroids 2,3,4-saturated fatty acyl CoAs 3-alpha-hydroxysteroids 6-aminopurines 7-hydroxysteroids Aminopyrimidines and derivatives Azacyclic compounds Beta amino acids and derivatives Carbothioic S-esters Coenzyme A and derivatives Cyclic alcohols and derivatives Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Ketones Medium-chain fatty acyl CoAs Monoalkyl phosphates Monosaccharide phosphates N-acyl amines N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Oxosteroids Pentose phosphates Polyols Primary amines Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Secondary alcohols Secondary carboxylic acid amides Steroidal glycosides Sulfenyl compounds Tetrahydrofurans Thioesters Trihydroxy bile acids, alcohols and derivatives 1,3-dicarbonyl compound 12-hydroxysteroid 24-oxosteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 6-aminopurine 7-hydroxysteroid Alcohol Alkyl phosphate Amine Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Beta amino acid or derivatives Bile acid, alcohol, or derivatives Carbonyl group Carbothioic s-ester Carboxamide group Carboxylic acid derivative Cholane-skeleton Coenzyme a or derivatives Cyclic alcohol Fatty amide Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Imidazole Imidazopyrimidine Imidolactam Ketone Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-acyl-amine N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Oxacycle Oxosteroid Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Polyol Primary amine Purine Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Pyrimidine Ribonucleoside 3'-phosphate Secondary alcohol Secondary carboxylic acid amide Steroid Steroidal glycoside Sulfenyl compound Tetrahydrofuran Thiocarboxylic acid ester Thiocarboxylic acid or derivatives Trihydroxy bile acid, alcohol, or derivatives Solid logp 0.82 ALOGPS logs -3.00 ALOGPS solubility 1.21e+00 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({2-methyl-3-oxo-6-[(1S,5R,7S,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 1214.154 ChemAxon mono_mass 1213.418432819 ChemAxon smiles [H][C@@]12CCC(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]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)C[C@]2([H])C[C@H](O)CCC12C ChemAxon formula C48H78N7O21P3S ChemAxon inchi InChI=1S/C48H78N7O21P3S/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/h22-30,32-34,36,38-40,44,56,58-59,61-62H,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-,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1 ChemAxon inchikey AWLXQJGPNLCTLM-XFQWJXLTSA-N ChemAxon polar_surface_area 441.39 ChemAxon refractivity 284.82 ChemAxon polarizability 119.51 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 21 ChemAxon donor_count 12 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::NmrOneD 92012 Specdb::NmrOneD 92013 Specdb::NmrOneD 92014 Specdb::NmrOneD 92015 Specdb::NmrOneD 92016 Specdb::NmrOneD 92017 Specdb::NmrOneD 92018 Specdb::NmrOneD 92019 Specdb::NmrOneD 92020 Specdb::NmrOneD 92021 Specdb::NmrOneD 92022 Specdb::NmrOneD 92023 Specdb::NmrOneD 92024 Specdb::NmrOneD 92025 Specdb::NmrOneD 92026 Specdb::NmrOneD 92027 Specdb::NmrOneD 92028 Specdb::NmrOneD 92029 Specdb::NmrOneD 92030 Specdb::NmrOneD 92031 Specdb::MsMs 304417 Specdb::MsMs 304418 Specdb::MsMs 304419 Specdb::MsMs 347614 Specdb::MsMs 347615 Specdb::MsMs 347616 Specdb::MsMs 2459626 Specdb::MsMs 2459627 Specdb::MsMs 2459628 Specdb::MsMs 2476007 Specdb::MsMs 2476008 Specdb::MsMs 2476009 HMDB06891 27379 #<Reference:0x000055ce31a54bc8> #<Reference:0x000055ce31a54a10> #<Reference:0x000055ce31a54858> #<Reference:0x000055ce31a546a0> 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-ketoacyl-CoA thiolase, mitochondrial P42765 ACAA2 3-ketoacyl-CoA thiolase, peroxisomal P09110 ACAA1 Non-specific lipid-transfer protein P22307 SCP2 Retinol dehydrogenase 13 Q8NBN7 RDH13 Trifunctional enzyme subunit beta, mitochondrial P55084 HADHB