3a,6a,7b-Trihydroxy-5b-cholanoic acid (CHEM034820)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:15:04 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034820
Identification
Common Name3a,6a,7b-Trihydroxy-5b-cholanoic acid
ClassSmall Molecule
DescriptionA member of the class of muricholic acids in which the hydroxy groups at positions 6 and 7 have alpha and beta configuration, respectively.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oic acidChEBI
Omega-mcaChEBI
Omega-muricholic acidKegg
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-OateGenerator
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-OateGenerator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-OateGenerator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oic acidGenerator
Omega-muricholateGenerator
3a,6a,7b-Trihydroxy-5b-cholanoateGenerator
3a,6a,7b-Trihydroxy-5b-cholan-24-OateHMDB
3a,6a,7b-Trihydroxy-5b-cholan-24-Oic acidHMDB
W-MuricholateHMDB
W-Muricholic acidHMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomerHMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomerHMDB
Trihydroxy-5 alpha-cholanoic acidHMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acidHMDB
alpha-Muricholic acidHMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomerHMDB
3,6,7-Trihydroxy-5-cholanoic acidHMDB
Muricholic acid, sodium saltHMDB
beta-Muricholic acidHMDB
Hyocholic acidHMDB
Muricholic acidHMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomerHMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomerHMDB
Chemical FormulaC24H40O5
Average Molecular Mass408.571 g/mol
Monoisotopic Mass408.288 g/mol
CAS Registry Number6830-03-1
IUPAC Name(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-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,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-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@@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-NTPBNISXSA-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
  • 7-alpha-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 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 Solubility0.069 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
Polarizability47.1 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-1010029000-e5824ce563bff12a309cSpectrum
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_1_4) - 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 (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 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_1_4) - 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_2_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0001900000-d3a03d40e1e660b47856Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4984300000-003497742d7b2b6ee004Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p7-4920000000-7110ab8e5a5670619051Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0009600000-56beda528763ce5ae6dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059j-3449200000-98d256091462f2bbd882Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-4951000000-c203ad5efbf5e653aa09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-68e3200734e1d0985f37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0009800000-a11781ffcf06d8bb288cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-3009300000-d354f18e540a94d7dfe1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000364
FooDB IDFDB021983
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5353
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446939
ChEBI ID81299
PubChem Compound ID5283851
Kegg Compound IDC17727
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10216137
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15604514
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20659429
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=403022
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=485143
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6824314
7. Iida, Takashi; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers. Journal of Lipid Research (1989), 30(8), 1267-79.
8. Nakashima T, Sano A, Seto Y, Nakajima T, Nakagawa Y, Okuno T, Takino T, Hasegawa T: Unusual trihydroxy bile acids in the urine of healthy humans. Clin Chim Acta. 1986 Oct 15;160(1):47-53.
9. 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.
10. 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.
11. 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.
12. 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.