Murocholic acid (CHEM034968)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:22:50 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034968
Identification
Common NameMurocholic acid
ClassSmall Molecule
DescriptionA 3alpha-hydroxy steroid that is cholan-24-oic acid substituted by hydroxy groups at positions 3 and 6.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha,6beta-Dihydroxy-5beta-cholanic acidChEBI
6beta-HydroxylithocholateChEBI
6beta-Hydroxylithocholic acidChEBI
MurideoxycholateChEBI
3a,6b-Dihydroxy-5b-cholanateGenerator
3a,6b-Dihydroxy-5b-cholanic acidGenerator
3alpha,6beta-Dihydroxy-5beta-cholanateGenerator
3Α,6β-dihydroxy-5β-cholanateGenerator
3Α,6β-dihydroxy-5β-cholanic acidGenerator
6b-HydroxylithocholateGenerator
6b-Hydroxylithocholic acidGenerator
6Β-hydroxylithocholateGenerator
6Β-hydroxylithocholic acidGenerator
Murideoxycholic acidGenerator
MurocholateGenerator
3a,6b-Dihydroxy-5b-cholan-24-OateHMDB
3a,6b-Dihydroxy-5b-cholan-24-Oic acidHMDB
3a,6b-Dihydroxy-5b-cholanoateHMDB
3a,6b-Dihydroxy-5b-cholanoic acidHMDB
3a,6b-DihydroxycholanoateHMDB
3a,6b-Dihydroxycholanoic acidHMDB
3,6-Dihydroxy-5alpha-cholanoic acidHMDB
NaHDC compoundHMDB
Hyodeoxycholic acidHMDB
Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomerHMDB
Hyodeoxycholic acid, (3alpha,6beta)-isomerHMDB
Hyodeoxycholic acid, sodium saltHMDB
Hyodesoxycholic acidHMDB
Sodium hyodeoxycholateHMDB
Murocholic acidChEBI
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number668-49-5
IUPAC Name(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21-,23-,24-/m1/s1
InChI KeyDGABKXLVXPYZII-PLYQRAMGSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.015 g/LALOGPS
logP2.98ALOGPS
logP3.71ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.58 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, Positivesplash10-004m-0329000000-58d5a781e1d72501a6fcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1100290000-3298b2503a68dd31087eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-c3986d5f0fc5c79bd19dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-035fbc6f30c118171a30Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-b6392133bd5f96611dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-581fe3701cfd4409cf1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-9218797d27b939f6059aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vl-1219000000-acd8de6ea11917fdc1bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0009000000-f969293bf286459bff3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0009000000-c32f7dbb58c16bc8f793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-a8bee4058c100d760c3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054o-0009000000-79e7c3afd290f34646cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3159000000-20e08d1a7b218eb91ebdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9681000000-7db68edc57414ccf438eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7eba834115ee2c679208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0009000000-375fefa884fafe6b05bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-2009000000-f58a3057b3e321a1006cSpectrum
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 IDHMDB0000811
FooDB IDFDB022259
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5775
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446909
ChEBI ID52030
PubChem Compound ID5283821
Kegg Compound IDC15515
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24399466
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8315264
3. Mitropoulos, K. A.; Myant, Nicolas B. Formation of lithocholic acid, chenodeoxycholic acid and other bile acids from 3b-hydroxychol-5-enoic acid in vitro and in vivo. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1967), 144(2), 430-9.
4. Iida T, Tazawa S, Ohshima Y, Niwa T, Goto J, Nambara T: Analysis of conjugated bile acids in human biological fluids. Synthesis of hyodeoxycholic acid 3- and 6-glycosides and related compounds. Chem Pharm Bull (Tokyo). 1994 Jul;42(7):1479-84.
5. Khallou J, Legrand-Defretin V, Parquet M, Coste T, Rautureau J, Lutton C: Metabolism and time-course excretion of murideoxycholic acid, a 6 beta-hydroxylated bile acid, in humans. J Hepatol. 1993 Mar;17(3):364-72.
6. 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.
7. 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.
8. 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.
9. 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.