Identification
Name20-hydroxycholesterol
Accession NumberDB04704
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII30060WAL99
CAS number516-72-3
WeightAverage: 402.6529
Monoisotopic: 402.349780716
Chemical FormulaC27H46O2
InChI KeyMCKLJFJEQRYRQT-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
17-alpha-hydroxylase deficiency (CYP17)DiseaseSMP00566
Corticosterone methyl oxidase I deficiency (CMO I)DiseaseSMP00577
SteroidogenesisMetabolicSMP00130
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyDiseaseSMP00373
21-hydroxylase deficiency (CYP21)DiseaseSMP00576
Apparent mineralocorticoid excess syndromeDiseaseSMP00717
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyDiseaseSMP00718
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDiseaseSMP00371
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencyDiseaseSMP00372
11-beta-hydroxylase deficiency (CYP11B1)DiseaseSMP00575
Corticosterone methyl oxidase II deficiency - CMO IIDiseaseSMP00578
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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 Parents3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
SubstituentsCholesterol / 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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsCholesterol and derivatives (LMST01010211 )
Drug created on September 11, 2007 11:49 / Updated on September 01, 2017 11:20