N-[(1R)-3-(4-HYDROXYPHENYL)-1-METHYLPROPYL]-2-(2-PHENYL-1H-INDOL-3-YL)ACETAMIDE

Identification

Name
N-[(1R)-3-(4-HYDROXYPHENYL)-1-METHYLPROPYL]-2-(2-PHENYL-1H-INDOL-3-YL)ACETAMIDE
Accession Number
DB07991
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: 398.4968
Monoisotopic: 398.199428086
Chemical Formula
C26H26N2O2
InChI Key
APLJSSOXDWUNGV-GOSISDBHSA-N
InChI
InChI=1S/C26H26N2O2/c1-18(11-12-19-13-15-21(29)16-14-19)27-25(30)17-23-22-9-5-6-10-24(22)28-26(23)20-7-3-2-4-8-20/h2-10,13-16,18,28-29H,11-12,17H2,1H3,(H,27,30)/t18-/m1/s1
IUPAC Name
N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-2-(2-phenyl-1H-indol-3-yl)acetamide
SMILES
[H][[email protected]@](C)(CCC1=CC=C(O)C=C1)NC(=O)CC1=C(NC2=C1C=CC=C2)C1=CC=CC=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
16750040
PubChem Substance
99444462
ChemSpider
20581160
BindingDB
50204815
ChEMBL
CHEMBL391910
HET
IOK
PDB Entries
2iok

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 Solubility0.000322 mg/mLALOGPS
logP5.09ALOGPS
logP5.26ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.12 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity120.55 m3·mol-1ChemAxon
Polarizability44.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9468
Caco-2 permeable-0.5228
P-glycoprotein substrateSubstrate0.5762
P-glycoprotein inhibitor INon-inhibitor0.9173
P-glycoprotein inhibitor IIInhibitor0.5229
Renal organic cation transporterNon-inhibitor0.6938
CYP450 2C9 substrateNon-substrate0.6942
CYP450 2D6 substrateNon-substrate0.692
CYP450 3A4 substrateSubstrate0.6621
CYP450 1A2 substrateInhibitor0.6956
CYP450 2C9 inhibitorNon-inhibitor0.5267
CYP450 2D6 inhibitorNon-inhibitor0.865
CYP450 2C19 inhibitorInhibitor0.6373
CYP450 3A4 inhibitorInhibitor0.7839
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8475
Ames testNon AMES toxic0.8524
CarcinogenicityNon-carcinogens0.9255
BiodegradationNot ready biodegradable0.9919
Rat acute toxicity2.5155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9702
hERG inhibition (predictor II)Non-inhibitor0.5744
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 2-phenylindoles. These are indoles substituted at the 2-position with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
2-phenylindoles
Alternative Parents
Phenylpyrroles / 3-alkylindoles / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
2-phenylindole / 2-phenylpyrrole / 3-alkylindole / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

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 15:27 / Updated on December 01, 2017 15:58