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

Identification

Name
(2R,3R,4S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL
Accession Number
DB07567
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 445.55
Monoisotopic: 445.225308485
Chemical Formula
C28H31NO4
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][[email protected]@]1(C)C2=CC(O)=CC=C2O[[email protected]@]([H])(C2=CC=C(OCCN3CCCC3)C=C2)[[email protected]@]1([H])C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4369568
PubChem Substance
99444038
ChemSpider
3572095
BindingDB
50162803
ChEBI
41593
ChEMBL
CHEMBL181936
HET
CM4
PDB Entries
1yim

Clinical Trials

Clinical Trials
Not Available

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
Polarizability50.08 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

Taxonomy

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
6-hydroxyflavonoid / Hydroxyisoflavonoid / Isoflavonoid / Isoflavonoid skeleton / Isoflavan / Flavan / Stilbene / Chromane / Benzopyran / 1-benzopyran
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-alkylpyrrolidine, chromanol (CHEBI:41593)

Targets

Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:23 / Updated on December 01, 2017 15:52