Record Information
Version1.0
Creation Date2016-05-26 05:41:20 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035358
Identification
Common Name5b-Cholestane-3a,7a,12a,25,26-pentol
ClassSmall Molecule
Description5b-Cholestane-3a,7a,12a,25,26-pentol is a bile alcohol. Bile alcohols have been found to be present as minor components in the bile and urine in healthy subjects. Bile alcohols are end products for cholesterol elimination as well as major biliary constituents; in mammals, cholesterol is metabolized by additional enzymes that ultimately transform it to bile acids. Bile alcohols are preferentially excreted as glucuronides into the urine, which constitute about 10% of total bile acids. Large amounts of bile alcohols have been found to be excreted into the bile and urine in patients with cerebrotendinous xanthomatosis (CTX), a rare inherited lipid storage disease. (PMID: 11718684).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(1R,3AS,3BR,4R,5as,7R,9as,9BS,11S,11ar)-1-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-4,7,11-triolChEBI
5 beta-BufolMeSH
Cholestane-3,7,12,25,26-pentolMeSH
3alpha,7alpha,12alpha,25,27-Pentahydroxy-5beta-cholestaneHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,25,26-pentolHMDB
5β-cholestane-3α,7α,12α,25,26-pentolHMDB
Chemical FormulaC27H48O5
Average Molecular Mass452.667 g/mol
Monoisotopic Mass452.350 g/mol
CAS Registry Number6127-75-9
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(O)CO
InChI IdentifierInChI=1S/C27H48O5/c1-16(6-5-10-25(2,32)15-28)19-7-8-20-24-21(14-23(31)27(19,20)4)26(3)11-9-18(29)12-17(26)13-22(24)30/h16-24,28-32H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1
InChI KeyXZDHXPDYLPEFQI-FIMPYCPFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentPentahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Pentahydroxy bile acid, alcohol, or derivatives
  • 26-hydroxysteroid
  • 25-hydroxysteroid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary 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 Solubility0.037 g/LALOGPS
logP2.57ALOGPS
logP2.46ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.25 m³·mol⁻¹ChemAxon
Polarizability54.12 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, Positivesplash10-00dr-0122900000-cacd8ec3923d61daccd4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-3420259000-648d14b08f09e307e0e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-8618d658ca789669b1baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0004900000-22410fc2bc2298d160a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvj-4107900000-b983cbc5bfc704cf4d16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0000900000-ffed7e90dd7b87a57738Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-170ee60a10c2959c3accSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6002900000-d1a8dea5f11077f0d132Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6340596647e37aa51756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-7e6e08a441b5c9d17841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6t-0002900000-d7d9e83916ffd4df656eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy0-0001900000-bb9301699f9d330b14b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-5244900000-a7ded1cf36b52b679158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-9862000000-c4b79935a8b6e0ea44a9Spectrum
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 IDHMDB0002180
FooDB IDFDB022890
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID194331
PubChem Compound ID5284194
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Nakagawa M, Une M, Takenaka S, Tazawa Y, Nozaki S, Imanaka T, Kuramoto T: Urinary bile alcohol profiles in healthy and cholestatic children. Clin Chim Acta. 2001 Dec;314(1-2):101-6.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11718684
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=181403
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1934504
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3559396
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7806978