Record Information
Version1.0
Creation date2011-09-21 00:08:16 UTC
Update date2015-07-21 06:56:58 UTC
Primary IDFDB022085
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5b-Cholestane-3a,7a,12a,23R,25-pentol
Description5b-Cholestane-3a,7a,12a,23R,25-pentol is a bile alcohol present in the urine of patients with cerebrotendinous xanthomatosis, but not in feces. A possible explanation for the urinary cholestanepentols is that the major serum bile alcohol, 5b-cholestane-3a,7a,12a,25-tetrol, might be hydroxylated at C-23 to form (23)-5b-cholestane-3a,7a,12a,23,25-pentols in the kidneys, an hypothesis supported by the fact that in our patient (23R)-5b-cholestane-3a,7a,12a,23,25-pentol was detected only in urine but were virtually absent in bile. (PMID 3700361) [HMDB]
CAS Number59906-14-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP2.33ALOGPS
logP2.05ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.34 m³·mol⁻¹ChemAxon
Polarizability53.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H48O5
IUPAC name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
InChI IdentifierInChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17-,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChI KeyOXSBBBPDYVCAKC-DYGXNTOZSA-N
Isomeric 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)C[C@@H](O)CC(C)(C)O
Average Molecular Weight452.667
Monoisotopic Molecular Weight452.350174646
Classification
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
  • Cholesterol
  • Cholesterol-skeleton
  • Pentahydroxy bile acid, alcohol, or derivatives
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • 23-hydroxysteroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-3324900000-4eb492177cd3ff3b1d78Spectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-1620339000-8ab1e57d5c6fb0da7063Spectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cholestane-3a,7a,12a,23R,25-pentol, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-ef4a2790d00f39151d5b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2005900000-a3c8abf978fcc74e3e282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-4209700000-0530fc30e51b3d5bdd052017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0002900000-33ffd4c8b139bf7602262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3004900000-c80999c8f40ac84967fb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9002000000-142d4259a51c5ae1ddec2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0409-0009700000-996ef26438e4bc39f3892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-4279500000-ec27c905a89e055a39d42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9850000000-991e1aa56ec25a12a3fc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-31db0067a7126bac24732021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-0003900000-68719f52b9a93bc9b3492021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0003900000-c260caf34cf5aecd15cf2021-09-23View Spectrum
NMRNot Available
ChemSpider ID13628096
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21252249
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00513
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
Processing...
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