NAV

20-hydroxycholesterol

Identification

Generic Name
20-hydroxycholesterol
DrugBank Accession Number
DB04704
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 402.6529
Monoisotopic: 402.349780716
Chemical Formula
C27H46O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
11-beta-Hydroxylase Deficiency (CYP11B1)Disease
Apparent Mineralocorticoid Excess SyndromeDisease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase DeficiencyDisease
Corticosterone Methyl Oxidase I Deficiency (CMO I)Disease
3-beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
SteroidogenesisMetabolic
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase DeficiencyDisease
17-alpha-Hydroxylase Deficiency (CYP17)Disease
21-Hydroxylase Deficiency (CYP21)Disease
Corticosterone Methyl Oxidase II Deficiency (CMO II)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
20-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cholesterol / Cholesterol-skeleton / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Cholesterol and derivatives (LMST01010211)
Affected organisms
Not Available

Chemical Identifiers

UNII
30060WAL99
CAS number
516-72-3
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,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2R)-2-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
SMILES
CC(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

References

General References
Not Available
Human Metabolome Database
HMDB0006283
PubChem Compound
440711
PubChem Substance
46508206
ChemSpider
389586
BindingDB
50035884
ChEMBL
CHEMBL1233249
ZINC
ZINC000004096811
PDBe Ligand
HC2
PDB Entries
1zhw / 3kyt

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability50.57 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-MSsplash10-007c-1139000000-2c00b5523723b960fa5a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0109100000-44ba4668eafc846156b9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-28cd625f7c243fbabd64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0670-5229100000-a9206f13dc70b0d894a6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-5648ea276f9c5466d9b5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0019600000-d74745035b6a892d32f1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9740000000-3522f302e044bdb80af3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-212.4848117
predicted
DarkChem Lite v0.1.0
[M-H]-198.90317
predicted
DeepCCS 1.0 (2019)
[M+H]+214.7443117
predicted
DarkChem Lite v0.1.0
[M+H]+201.14616
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.0168117
predicted
DarkChem Lite v0.1.0
[M+Na]+206.912
predicted
DeepCCS 1.0 (2019)

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52