7a-Hydroxy-5b-cholanic acid (CHEM035446)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:46:28 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035446
Identification
Common Name7a-Hydroxy-5b-cholanic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Deoxy-cdcaChEBI
3-DeoxyCDCAChEBI
7alpha-Hydroxy-5beta-cholan-24-Oic acidChEBI
7alpha-Hydroxy-5beta-cholanic acidChEBI
7a-Hydroxy-5b-cholan-24-OateGenerator
7a-Hydroxy-5b-cholan-24-Oic acidGenerator
7alpha-Hydroxy-5beta-cholan-24-OateGenerator
7Α-hydroxy-5β-cholan-24-OateGenerator
7Α-hydroxy-5β-cholan-24-Oic acidGenerator
7a-Hydroxy-5b-cholanateGenerator
7alpha-Hydroxy-5beta-cholanateGenerator
7Α-hydroxy-5β-cholanateGenerator
7Α-hydroxy-5β-cholanic acidGenerator
7a-Hydroxy-5b-cholanoateHMDB
7a-Hydroxy-5b-cholanoic acidHMDB
3-DeoxychenodeoxycholateHMDB
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
7a-Hydroxy-5b-cholanic acidGenerator
Chemical FormulaC24H40O3
Average Molecular Mass376.573 g/mol
Monoisotopic Mass376.298 g/mol
CAS Registry Number28083-34-3
IUPAC Name(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name7a-hydroxy-5b-cholanate
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
InChI IdentifierInChI=1S/C24H40O3/c1-15(7-10-21(26)27)17-8-9-18-22-19(11-13-24(17,18)3)23(2)12-5-4-6-16(23)14-20(22)25/h15-20,22,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI KeyJVMCMMXFADJQKU-MMSVWBHPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0011 g/LALOGPS
logP4.15ALOGPS
logP5.1ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.6 m³·mol⁻¹ChemAxon
Polarizability45.32 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1339000000-1748426d33d8bf6471baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-3223790000-4331610c0e43e0cee3fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-98131836749f94b76c63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-1029000000-216b5ad98f22d08968d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7449000000-5df9cadfecbc48722ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f317b23fea7a9c31f96aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0009000000-501cf707675b3017b6f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-8fb62cb5d050060eef79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-eccc9e9b8c78169f5313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0009000000-c70b5dcd12e8a885117cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1019000000-6b99886aca5e81ddc24aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-f182918fe0e4a71a91abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-6059000000-87535fcb28c834e2c8cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9240000000-b03351da33b1bdb913ffSpectrum
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 IDHMDB0002492
FooDB IDFDB023013
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6700
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID394733
ChEBI ID73676
PubChem Compound ID447718
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hara, Shoji. Aza steroids. IV. Synthesis of B-azacholane derivative. Yakugaku Zasshi (1958), 78 1030-3.
2. 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.
3. 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.
4. 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.
5. 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.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12718893