Record Information
Version1.0
Creation date2011-09-21 00:36:11 UTC
Update date2015-07-21 06:57:55 UTC
Primary IDFDB023876
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20alpha-Hydroxycholesterol
Description20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol. Based on a literature review very few articles have been published on 20alpha-Hydroxycholesterol.
CAS Number516-72-3
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP6.06ALOGPS
logP5.8ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.3 m³·mol⁻¹ChemAxon
Polarizability51.1 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,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
InChI IdentifierInChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI KeyMCKLJFJEQRYRQT-MGNSQDQZSA-N
Isomeric SMILESCC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
Classification
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 20-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

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-MS20alpha-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007c-1139000000-2c00b5523723b960fa5aSpectrum
Predicted GC-MS20alpha-Hydroxycholesterol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3011490000-84aa9e3675270a653af2Spectrum
Predicted GC-MS20alpha-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS20alpha-Hydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-78634a50a076fbe309752017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-3039100000-08dfa0b5e30063e9930a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-8189000000-c3bb06d3d099c9c4f4402017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-4b881293f669607058cc2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1039800000-4c4801e96fa5d9126da52017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-3089000000-806365cc5d181d0d25d92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0009500000-63d3ce6872e526ad179d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f9i-0109100000-ba23251dfb42b1ea90e72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9147100000-ed7f14edc5be9509ea462021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9820000000-1d6a29936460689277862021-09-24View Spectrum
NMRNot Available
ChemSpider ID389586
ChEMBL IDCHEMBL1233249
KEGG Compound IDC05500
Pubchem Compound ID440711
Pubchem Substance IDNot Available
ChEBI ID1296
Phenol-Explorer IDNot Available
DrugBank IDDB04704
HMDB IDHMDB06283
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1443018
KNApSAcK IDNot Available
HET IDHC2
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