alpha-Muricholic acid (CHEM034884)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:18:11 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034884
Identification
Common Namealpha-Muricholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-MuricholateGenerator
a-Muricholic acidGenerator
alpha-MuricholateGenerator
Α-muricholateGenerator
Α-muricholic acidGenerator
3a,6b,7a-Trihydroxy-5b-cholan-24-OateHMDB
3a,6b,7a-Trihydroxy-5b-cholan-24-Oic acidHMDB
3a,6b,7a-Trihydroxy-5b-cholanateHMDB
3a,6b,7a-Trihydroxy-5b-cholanic acidHMDB
5b-Cholanic acid-3a,6b,7a-triolHMDB
(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
Chemical FormulaC24H40O5
Average Molecular Mass408.571 g/mol
Monoisotopic Mass408.288 g/mol
CAS Registry Number2393-58-0
IUPAC Name(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15?,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1
InChI KeyDKPMWHFRUGMUKF-LPMPYYIQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 6-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Solubility0.069 g/LALOGPS
logP2.16ALOGPS
logP2.72ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.56 m³·mol⁻¹ChemAxon
Polarizability47.08 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, Positivesplash10-004l-0329000000-fed34af3d93baa3f7367Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1110029000-d964e134586fffeb9133Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0009100000-aeaf5bcdde74fe1ddf76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0009000000-4af1ebd01d1d670d4f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003u-2209000000-454d741b691e592d251aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0007900000-e501198616f74730538fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009300000-9efc23876fa89e243bc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9007000000-e5bd870e3f9870c89a14Spectrum
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 IDHMDB0000506
FooDB IDFDB022082
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5492
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477700
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hsia, S. L.; Elliott, Wm. H.; Matschiner, John T.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A. Bile acids. XIII. Further contributions to the constitution of muricholic acids. Journal of Biological Chemistry (1960), 235 1963-7.
2. Hsia, S. L.; Elliott, Wm. H.; Matschiner, John T.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A. Bile acids. XIII. Further contributions to the constitution of muricholic acids. Journal of Biological Chemistry (1960), 235 1963-7.
3. Goto J, Hasegawa K, Nambara T, Iida T: Studies on steroids. CCLIV. Gas chromatographic-mass spectrometric determination of 4- and 6-hydroxylated bile acids in human urine with negative ion chemical ionization detection. J Chromatogr. 1992 Feb 7;574(1):1-7.
4. Ikawa S, Miyake M, Mura T, Ikeguchi M: High-performance liquid chromatographic-fluorescence determination of human faecal bile acids. J Chromatogr. 1987 Jul 29;400:149-61.
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.