Record Information
Version1.0
Creation date2011-09-21 00:27:31 UTC
Update date2018-05-28 18:36:20 UTC
Primary IDFDB023285
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name22beta-Hydroxycholesterol
Description22b-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number22348-64-7
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP5.69ALOGPS
logP5.8ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m³·mol⁻¹ChemAxon
Polarizability50.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H46O2
IUPAC name(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
InChI IdentifierInChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1
InChI KeyRZPAXNJLEKLXNO-GFKLAVDKSA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
Classification
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Dihydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 3-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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-MS22beta-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-1009000000-ed60780a407ecfba86a3Spectrum
Predicted GC-MS22beta-Hydroxycholesterol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2111490000-e04dc3bb7ab36f5571f8Spectrum
Predicted GC-MS22beta-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS22beta-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-2ae8fb6172d46e818cef2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2119100000-9925177c38f63ddc14a12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6049000000-44d8c7fcd6055391f8dd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0004900000-10b9f0186b2a2ac37d532016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1019700000-6b5a6ee8410d635f82c62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4059000000-8d88574ef4b0b7d39b852016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0109200000-bd7670f27e11ece2eac02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-5339000000-858a48abc2f1b02935f52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6960000000-73b0982e9fcef4fa83d02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-84d3363c4aa86f104c552021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0012900000-973e1345841477d95a762021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uea-7049300000-8042d2ca5cd8469196da2021-09-25View Spectrum
NMRNot Available
ChemSpider ID146693
ChEMBL IDCHEMBL422904
KEGG Compound IDC05502
Pubchem Compound ID167685
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04035
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDHC9
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
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference