7b-Hydroxy-3-oxo-5b-cholanoic acid (CHEM034898)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:18:52 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034898
Identification
Common Name7b-Hydroxy-3-oxo-5b-cholanoic acid
ClassSmall Molecule
Description7b-Hydroxy-3-oxo-5b-cholanoic acid was one of the bile acids present in significant proportions during early gestation, identified in amniotic fluid. (PMID 2373959). 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7b-Hydroxy-3-oxo-5b-cholanoateGenerator
(5b,7b)-7-Hydroxy-3-oxo-cholan-24-OateHMDB
(5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oic acidHMDB
7b-Hydroxy-3-oxo-5b-cholan-24-OateHMDB
7b-Hydroxy-3-oxo-5b-cholan-24-Oic acidHMDB
Methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acidHMDB
Methyl 3,7-dioxocholan-24-Oic acidHMDB
Chemical FormulaC25H38O4
Average Molecular Mass402.567 g/mol
Monoisotopic Mass402.277 g/mol
CAS Registry Number77060-26-5
IUPAC Namemethyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate
Traditional Name7b-hydroxy-3-oxo-5b-cholanoate
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1
InChI KeyUZRRNRRCPZZPNY-ZECRIGHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentBile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Bile acid, alcohol, or derivatives
  • 3-oxosteroid
  • 7-oxosteroid
  • Oxosteroid
  • Fatty acid methyl ester
  • Fatty acid ester
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP3.74ALOGPS
logP4.45ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.52ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.09 m³·mol⁻¹ChemAxon
Polarizability47.31 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0329000000-1e963f0efc062b4c2cb5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0009300000-5e68f1155f43364368d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi3-0009000000-5a0857da406ad953bdf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02dl-1219000000-395d89c81920965d4670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0005900000-d036026313030bd5da80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1009500000-df1cd4b80e2081404b17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9008000000-8a340a2d89e658182c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0005900000-0bc1a9421d158a94047fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-2009600000-b4cde42c186303ed0cccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r7-2039000000-23f857864c5619a6ddf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019200000-a18b41e6209e796f3ccfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0069000000-88b60d74b3b44ae039a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-1972000000-a4d5bf25c6c82b5fdbf0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000541
FooDB IDFDB022104
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5526
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17215969
ChEBI ID172644
PubChem Compound ID22833531
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Forlani, Roberto; Maietti, Silvia; Pedrini, Paola. Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids. Journal of Organic Chemistry (2002), 67(16), 5802-5806.
2. Nakagawa M, Setchell KD: Bile acid metabolism in early life: studies of amniotic fluid. J Lipid Res. 1990 Jun;31(6):1089-98.
3. Koopman BJ, Wolthers BG, van der Molen JC, Nagel GT, Kruizinga W: Abnormal urinary bile acids in a patient suffering from cerebrotendinous xanthomatosis during oral administration of ursodeoxycholic acid. Biochim Biophys Acta. 1987 Feb 14;917(2):238-46.
4. Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9.
5. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.
6. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.
7. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.
8. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.