NAV

25-Hydroxycholesterol

Identification

Generic Name
25-Hydroxycholesterol
DrugBank Accession Number
DB04705
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 402.6529
Monoisotopic: 402.349780716
Chemical Formula
C27H46O2
Synonyms
  • 5-Cholestene-3beta,25-diol
  • Cholest-5-ene-3beta,25-diol
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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
3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
25-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
oxysterol, 25-hydroxy steroid (CHEBI:42977) / Cholesterol and derivatives (LMST01010018)
Affected organisms
Not Available

Chemical Identifiers

UNII
767JTD2N31
CAS number
2140-46-7
InChI Key
INBGSXNNRGWLJU-ZHHJOTBYSA-N
InChI
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
IUPAC Name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R)-6-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
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)(C)O

References

General References
Not Available
KEGG Compound
C15519
PubChem Compound
65094
PubChem Substance
46506794
ChemSpider
58604
BindingDB
20182
ChEBI
42977
ChEMBL
CHEMBL169046
ZINC
ZINC000005751264
PDBe Ligand
HC3
PDB Entries
1zhx / 3gkj / 3l0l / 6bym / 6gqf / 6m49 / 6t4x / 6t4y / 6t50 / 8ivf

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 Solubility0.000244 mg/mLALOGPS
logP5.95ALOGPS
logP5.64Chemaxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.2Chemaxon
pKa (Strongest Basic)-1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity122.45 m3·mol-1Chemaxon
Polarizability51.11 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0909-2809000000-be382c4f133b8a79f8d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-48369659f635aaa04a70
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001900000-9cbc9b3cd0591a4986d5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00li-9223100000-468a05df6545823a2f91
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0037900000-e4c930b47e64047ccd0f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-3890000000-64322d78818e11c2ce10
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]-221.0052117
predicted
DarkChem Lite v0.1.0
[M-H]-220.4208117
predicted
DarkChem Lite v0.1.0
[M-H]-202.86926
predicted
DeepCCS 1.0 (2019)
[M+H]+218.4623117
predicted
DarkChem Lite v0.1.0
[M+H]+216.9452117
predicted
DarkChem Lite v0.1.0
[M+H]+205.26149
predicted
DeepCCS 1.0 (2019)
[M+Na]+221.2926117
predicted
DarkChem Lite v0.1.0
[M+Na]+217.6927117
predicted
DarkChem Lite v0.1.0
[M+Na]+211.174
predicted
DeepCCS 1.0 (2019)

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