NAV

7beta-hydroxycholesterol

Identification

Generic Name
7beta-hydroxycholesterol
DrugBank Accession Number
DB04706
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 402.6529
Monoisotopic: 402.349780716
Chemical Formula
C27H46O2
Synonyms
  • (3β,7β)-cholest-5-ene-3,7-diol
  • 7β-hydroxycholesterol
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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
Not Available
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
7-alpha-hydroxysteroids / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / 7-alpha-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cholesterol / Cholesterol-skeleton
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
oxysterol, 7beta-hydroxy steroid (CHEBI:42989) / Cholesterol and derivatives (LMST01010047)
Affected organisms
Not Available

Chemical Identifiers

UNII
N9616291J4
CAS number
566-27-8
InChI Key
OYXZMSRRJOYLLO-KGZHIOMZSA-N
InChI
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
IUPAC Name
(1R,3aS,3bS,4R,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-4,7-diol
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

References

General References
Not Available
Human Metabolome Database
HMDB0006119
PubChem Compound
473141
PubChem Substance
46505045
ChemSpider
415508
BindingDB
50045545
ChEBI
42989
ChEMBL
CHEMBL497834
ZINC
ZINC000005758832
PDBe Ligand
HCR
PDB Entries
1zht

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 Solubility0.000476 mg/mLALOGPS
logP5.61ALOGPS
logP5.96Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.2Chemaxon
pKa (Strongest Basic)-0.83Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity122.06 m3·mol-1Chemaxon
Polarizability51.12 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-1229000000-8b7536c0aaf1a204c485
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-2016900000-267c1832f99122f951e8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0002900000-00b12c268e0a541a2976
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-5648ea276f9c5466d9b5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-9223100000-413e7fbb884abcdfce86
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009800000-9d7951b2f9de4fd9057b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pbl-8790000000-2a4857b455fe36eedd2a
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]-211.4077117
predicted
DarkChem Lite v0.1.0
[M-H]-206.5533117
predicted
DarkChem Lite v0.1.0
[M-H]-211.66342
predicted
DeepCCS 1.0 (2019)
[M+H]+209.0329117
predicted
DarkChem Lite v0.1.0
[M+H]+203.8650117
predicted
DarkChem Lite v0.1.0
[M+H]+213.55882
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.6023117
predicted
DarkChem Lite v0.1.0
[M+Na]+203.1674117
predicted
DarkChem Lite v0.1.0
[M+Na]+219.3883
predicted
DeepCCS 1.0 (2019)

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