(2R,3R,4S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL

Identification

Generic Name
(2R,3R,4S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL
DrugBank Accession Number
DB07567
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 445.55
Monoisotopic: 445.225308485
Chemical Formula
C28H31NO4
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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 6-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-6 position of the flavonoid skeleton.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Hydroxyflavonoids
Direct Parent
6-hydroxyflavonoids
Alternative Parents
Hydroxyisoflavonoids / Isoflavans / Flavans / Stilbenes / 1-benzopyrans / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / N-alkylpyrrolidines
show 5 more
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 6-hydroxyflavonoid / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzopyran / Chromane
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-alkylpyrrolidine, chromanol (CHEBI:41593)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XPVKGTWRXBSJKO-LHXLBICKSA-N
InChI
InChI=1S/C28H31NO4/c1-19-25-18-23(31)10-13-26(25)33-28(27(19)20-4-8-22(30)9-5-20)21-6-11-24(12-7-21)32-17-16-29-14-2-3-15-29/h4-13,18-19,27-28,30-31H,2-3,14-17H2,1H3/t19-,27-,28+/m1/s1
IUPAC Name
(2R,3R,4S)-3-(4-hydroxyphenyl)-4-methyl-2-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3,4-dihydro-2H-1-benzopyran-6-ol
SMILES
[H][C@@]1(C)C2=CC(O)=CC=C2O[C@@]([H])(C2=CC=C(OCCN3CCCC3)C=C2)[C@@]1([H])C1=CC=C(O)C=C1

References

General References
Not Available
PubChem Compound
4369568
PubChem Substance
99444038
ChemSpider
3572095
BindingDB
50162803
ChEBI
41593
ChEMBL
CHEMBL181936
ZINC
ZINC000016051697
PDBe Ligand
CM4
PDB Entries
1yim

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 Solubility0.00444 mg/mLALOGPS
logP5.26ALOGPS
logP5.17Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)9.78Chemaxon
pKa (Strongest Basic)8.9Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area62.16 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity129.81 m3·mol-1Chemaxon
Polarizability49.87 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier+0.9174
Caco-2 permeable-0.6159
P-glycoprotein substrateSubstrate0.7921
P-glycoprotein inhibitor INon-inhibitor0.5487
P-glycoprotein inhibitor IIInhibitor0.9063
Renal organic cation transporterInhibitor0.6239
CYP450 2C9 substrateNon-substrate0.8086
CYP450 2D6 substrateNon-substrate0.6137
CYP450 3A4 substrateSubstrate0.6106
CYP450 1A2 substrateNon-inhibitor0.6012
CYP450 2C9 inhibitorNon-inhibitor0.878
CYP450 2D6 inhibitorInhibitor0.6771
CYP450 2C19 inhibitorInhibitor0.5072
CYP450 3A4 inhibitorInhibitor0.625
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7728
Ames testNon AMES toxic0.8502
CarcinogenicityNon-carcinogens0.946
BiodegradationNot ready biodegradable0.9799
Rat acute toxicity2.4754 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8024
hERG inhibition (predictor II)Inhibitor0.5801
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/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

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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]

Drug created at September 15, 2010 21:23 / Updated at June 12, 2020 16:52