Record Information
Version1.0
Creation date2011-09-21 00:05:36 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021943
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid
DescriptionA 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]
CAS Number60696-60-8
Structure
Thumb
Synonyms
SynonymSource
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoateGenerator
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-OateHMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oic acidHMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoicHMDB
2b-HydroxycholateHMDB
2b-Hydroxycholic acidHMDB
(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oatehmdb
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic acidhmdb
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.34ALOGPS
logP1.41ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.15 m³·mol⁻¹ChemAxon
Polarizability48.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H40O6
IUPAC name(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13-,14?,15?,16?,17-,18+,19-,20-,22?,23-,24+/m0/s1
InChI KeyIMMADCCLTPCOKH-DLPNMVJGSA-N
Isomeric SMILES[H][C@@]12C[C@H](O)[C@@H](O)C[C@]1(C)C1C[C@H](O)[C@]3(C)C(CCC3C1[C@H](O)C2)[C@@H](C)CCC(O)=O
Average Molecular Weight424.5708
Monoisotopic Molecular Weight424.282489012
Classification
Description Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056u-0349200000-b0b08f5856ad6c87f694Spectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1100169000-a315711d7850b06d1e6dSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0009700000-4bd7fcfff99cc3ef2be3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0109200000-4e4820960d8c18237874Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-2109000000-0e0f6d299d25f4f2ab0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0003900000-eb918affd2e4c283a1bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1006900000-08a37999c1ecae279d7dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006100000-c42e6ca2acaaf03f9f53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0007900000-d133c2ed974bbe01feebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1329200000-37c56b59a2af41ecda9bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9550000000-3ce7e188c553f66bcdebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-f2b8ea5cd784108b4f12Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0001900000-087880e8ccd5371d10c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022i-1009200000-34b17fc126fb16670448Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477680
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00316
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference