Identification

Generic Name
2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol
DrugBank Accession Number
DB08773
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 242.293
Monoisotopic: 242.040150254
Chemical Formula
C14H10O2S
Synonyms
  • 2-(4-hydroxyphenyl)benzo(b)thiophene-6-ol
  • Raloxifene core

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
UNuclear receptor coactivator 2Not AvailableHumans
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
Adverseeffects
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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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiophenes
Sub Class
1-benzothiophenes
Direct Parent
1-benzothiophenes
Alternative Parents
2,3,5-trisubstituted thiophenes / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Heteroaromatic compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-benzothiophene / 1-hydroxy-2-unsubstituted benzenoid / 2,3,5-trisubstituted thiophene / Aromatic heteropolycyclic compound / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
8ZK5PJ1CM3
CAS number
63676-22-2
InChI Key
MDGWZLQPNOETLH-UHFFFAOYSA-N
InChI
InChI=1S/C14H10O2S/c15-11-4-1-9(2-5-11)13-7-10-3-6-12(16)8-14(10)17-13/h1-8,15-16H
IUPAC Name
2-(4-hydroxyphenyl)-1-benzothiophen-6-ol
SMILES
OC1=CC=C(C=C1)C1=CC2=C(S1)C=C(O)C=C2

References

General References
Not Available
PubChem Compound
445920
PubChem Substance
99445244
ChemSpider
393408
BindingDB
20628
ChEMBL
CHEMBL431698
ZINC
ZINC000003581478
PDBe Ligand
ZTW
PDB Entries
1gwq

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 Solubility0.0104 mg/mLALOGPS
logP3.57ALOGPS
logP3.89ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.28 m3·mol-1ChemAxon
Polarizability25.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.778
Caco-2 permeable+0.5591
P-glycoprotein substrateNon-substrate0.6475
P-glycoprotein inhibitor INon-inhibitor0.9452
P-glycoprotein inhibitor IINon-inhibitor0.8046
Renal organic cation transporterNon-inhibitor0.8404
CYP450 2C9 substrateNon-substrate0.6627
CYP450 2D6 substrateNon-substrate0.8705
CYP450 3A4 substrateNon-substrate0.6894
CYP450 1A2 substrateInhibitor0.829
CYP450 2C9 inhibitorInhibitor0.7729
CYP450 2D6 inhibitorNon-inhibitor0.8312
CYP450 2C19 inhibitorInhibitor0.7062
CYP450 3A4 inhibitorNon-inhibitor0.6423
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.885
Ames testAMES toxic0.625
CarcinogenicityNon-carcinogens0.8626
BiodegradationNot ready biodegradable0.9558
Rat acute toxicity2.1868 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9648
hERG inhibition (predictor II)Non-inhibitor0.7688
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

Targets

Drugtargets2
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Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
Gene Name
NCOA2
Uniprot ID
Q15596
Uniprot Name
Nuclear receptor coactivator 2
Molecular Weight
159155.645 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52