Record Information
Version1.0
Creation Date2014-08-29 06:51:37 UTC
Update Date2016-11-09 01:09:08 UTC
Accession NumberCHEM003434
Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholestanoic acid
ClassSmall Molecule
Description3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid is a 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.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Mammal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-Oic acidChEBI
(3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-Oic acidGenerator
(3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-Oic acidGenerator
3a,7a,12a-Trihydroxy-5b-cholestanoateGenerator
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-OateHMDB
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-Oic acidHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestanateHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoateHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acidHMDB
Chemical FormulaC27H46O5
Average Molecular Mass450.651 g/mol
Monoisotopic Mass450.335 g/mol
CAS Registry Number33964-75-9
IUPAC Name(2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
Traditional Name(2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC[C@@H](C)C(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChI KeyCNWPIIOQKZNXBB-WBYPBBSPSA-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
  • Steroid acid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid (CHEBI:48043 )
  • C27 bile acids, alcohols, and derivatives (LMST04030151 )
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 Not Available
Zellweger SyndromeSMP00316 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.12ALOGPS
logP3.91ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.57 m³·mol⁻¹ChemAxon
Polarizability53.21 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0353900000-c3bc744526d90b133841Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1341349000-6c72d8109d5d5eae56d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-adf6831ff2e0a9c5ca12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-0018900000-a785d8993c7e11e2a341Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-1309300000-695e056a38badf6cf6e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-e61f4254ed98eb0cde09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001s-0003900000-c0a96180a836b10b4d77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-9008700000-6d14292657023708cb78Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid is a bile acid. 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003873
FooDB IDFDB023241
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21865494
ChEBI ID48043
PubChem Compound ID23657849
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available