Back to Compounds

(24R)-Cholest-5-ene-3-beta,24-diol (FDB028339)

Record Information
Version1.0
Creation date2011-09-21 01:38:14 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028339
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(24R)-Cholest-5-ene-3-beta,24-diol
Description(24R)-Cholest-5-ene-3-beta,24-diol or 24(R)-Hydroxycholesterol is a hydroxysterol. It is a substrate for Cytochrome P450 39A1 (EC 1.14.13.99), which is primarily a liver-specific enzyme. It is involved in the following reaction: (24R)-cholest-5-ene-3-beta,24-diol + NADPH + O(2) = (24R)-cholest-5-ene-3-beta,7-alpha,24-triol + NADP(+) + H(2)O. 24(R)-Hydroxycholesterol is an intermediate in bile acid metabolism. The majority of circulating 24-hydroxycholesterol in humans is made in the brain and is increased in serum of Alzheimer patients. 24(S)-Hydroxycholesterol is generally more abundant in human tissues than 24(R)-Hydroxycholesterol. It has also been shown that 24(R) and 24(S)-Hydroxycholesterols are substrates for hepatic cholesterol 7-a hydroxylase (CYP7A), leading to the production of 7-alpha hydroxylated bile acids. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0004 g/LALOGPS
logP5.7ALOGPS
logP5.8ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m³·mol⁻¹ChemAxon
Polarizability50.94 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,15R)-14-[(2R,5R)-5-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)25(29)11-6-18(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-/m1/s1
InChI KeyIOWMKBFJCNLRTC-BPWUYGJYSA-N
Isomeric SMILES[H][C@@]12CCC([C@H](C)CC[C@@H](O)C(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
  • 24-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,24-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0076-1009000000-918c634f2e40ac4fb8c3Spectrum
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,24-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2111290000-94668570804377216a37Spectrum
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,24-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-db2e1b276e6052150b6f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0009700000-55fe1a48489ad8aa8bb62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ri-7009000000-7a2a5d9fa1c30ba0c55b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2002900000-8f2c13356a2deb497dc52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-3019200000-8713943f0050708c3c272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-0f92e092c978feb7ef4a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4119100000-6a8569b9873ebded521a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c01-5049000000-3466fdb5c0a23399bea32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0209100000-bfa601e19f304e87cbf02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vu-4559000000-a66619fe39b0d508ca4c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5962000000-9419106f12041db2bda52021-09-22View Spectrum
NMRNot Available
ChemSpider ID26626774
ChEMBL IDCHEMBL1867391
KEGG Compound IDNot Available
Pubchem Compound ID53481009
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11643
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
FoodReference
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