20-hydroxycholesterol

Identification

Name
20-hydroxycholesterol
Accession Number
DB04704
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
30060WAL99
CAS number
516-72-3
Weight
Average: 402.6529
Monoisotopic: 402.349780716
Chemical Formula
C27H46O2
InChI Key
MCKLJFJEQRYRQT-MGNSQDQZSA-N
InChI
InChI=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
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
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
17-alpha-hydroxylase deficiency (CYP17)Disease
Corticosterone methyl oxidase I deficiency (CMO I)Disease
SteroidogenesisMetabolic
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyDisease
21-hydroxylase deficiency (CYP21)Disease
Apparent mineralocorticoid excess syndromeDisease
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencyDisease
11-beta-hydroxylase deficiency (CYP11B1)Disease
Corticosterone methyl oxidase II deficiency - CMO IIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB06283
PubChem Compound
440711
PubChem Substance
46508206
ChemSpider
389586
ChEMBL
CHEMBL1233249
HET
HC2
PDB Entries
1zhw / 3kyt

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000571 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.3 m3·mol-1ChemAxon
Polarizability51.1 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9469
Caco-2 permeable+0.8723
P-glycoprotein substrateSubstrate0.7245
P-glycoprotein inhibitor INon-inhibitor0.6446
P-glycoprotein inhibitor IIInhibitor0.6131
Renal organic cation transporterNon-inhibitor0.7719
CYP450 2C9 substrateNon-substrate0.8252
CYP450 2D6 substrateNon-substrate0.8744
CYP450 3A4 substrateSubstrate0.7944
CYP450 1A2 substrateNon-inhibitor0.8907
CYP450 2C9 inhibitorNon-inhibitor0.927
CYP450 2D6 inhibitorNon-inhibitor0.9429
CYP450 2C19 inhibitorNon-inhibitor0.8107
CYP450 3A4 inhibitorNon-inhibitor0.8517
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5193
Ames testNon AMES toxic0.7963
CarcinogenicityNon-carcinogens0.9277
BiodegradationNot ready biodegradable0.9871
Rat acute toxicity3.0155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8189
hERG inhibition (predictor II)Non-inhibitor0.7523
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Cholestane steroids
Direct Parent
Cholesterols and derivatives
Alternative Parents
3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
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
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Cholesterol and derivatives (LMST01010211)

Drug created on September 11, 2007 11:49 / Updated on November 09, 2017 03:45