1.0 2011-09-21 00:06:25 UTC 2015-07-21 06:56:55 UTC FDB021979 3a,7a-Dihydroxycoprostanic acid 3a,7a-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID 864325) 3a,7a-Dihydroxycoprostanic acid is the precursor to chenodeoxycholic acid 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. [HMDB] 3a,7a-Dihydroxy-5b-cholestan-26-oate 3a,7a-Dihydroxy-5b-cholestan-26-oic acid 3a,7a-Dihydroxy-5b-cholestanoate 3a,7a-Dihydroxy-5b-cholestanoic acid 3a,7a-Dihydroxycoprostanate 3a,7a-Dihydroxycoprostanic acid 3a,7a-Hydroxy-5b-cholestan-26-oate 3a,7a-Hydroxy-5b-cholestan-26-oic acid 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oate 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acid 3alpha,7alpha-Dihydroxy-5beta-cholestanate 3alpha,7alpha-dihydroxy-5beta-cholestanic acid 3alpha,7alpha-Dihydroxy-5beta-cholestanoate 3alpha,7alpha-dihydroxy-5beta-cholestanoic acid C27H46O4 434.6517 434.33960996 (6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid (6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid 17974-66-2 [H][C@@]1(CC[C@@]2([H])C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24?,26+,27-/m1/s1 ITZYGDKGRKKBSN-KLYSAGIUSA-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 derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Steroid acids 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Dihydroxy bile acid, alcohol, or derivatives Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Hydroxysteroid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Steroid acid Solid logp 4.02 ALOGPS logs -5.00 ALOGPS solubility 4.36e-03 g/l ALOGPS logp 5.15 ChemAxon pka_strongest_acidic 4.83 ChemAxon pka_strongest_basic -0.54 ChemAxon iupac (6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid ChemAxon average_mass 434.6517 ChemAxon mono_mass 434.33960996 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O ChemAxon formula C27H46O4 ChemAxon inchi InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24?,26+,27-/m1/s1 ChemAxon inchikey ITZYGDKGRKKBSN-KLYSAGIUSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 123.05 ChemAxon polarizability 52.47 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::MsMs 288037 Specdb::MsMs 288038 Specdb::MsMs 288039 Specdb::MsMs 327028 Specdb::MsMs 327029 Specdb::MsMs 327030 Specdb::CMs 9960 Specdb::CMs 37462 HMDB00359 #<Reference:0x0000561272d5d600> Bile acid-CoA:amino acid N-acyltransferase Q14032 BAAT Bile acyl-CoA synthetase Q9Y2P5 SLC27A5