4-{[(2R)-2-(2-methylphenyl)pyrrolidin-1-yl]carbonyl}benzene-1,3-diol

Identification

Name
4-{[(2R)-2-(2-methylphenyl)pyrrolidin-1-yl]carbonyl}benzene-1,3-diol
Accession Number
DB08442
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: 297.3484
Monoisotopic: 297.136493479
Chemical Formula
C18H19NO3
InChI Key
TWODFUZHWYZBHZ-MRXNPFEDSA-N
InChI
InChI=1S/C18H19NO3/c1-12-5-2-3-6-14(12)16-7-4-10-19(16)18(22)15-9-8-13(20)11-17(15)21/h2-3,5-6,8-9,11,16,20-21H,4,7,10H2,1H3/t16-/m1/s1
IUPAC Name
4-[(2R)-2-(2-methylphenyl)pyrrolidine-1-carbonyl]benzene-1,3-diol
SMILES
[H][[email protected]@]1(CCCN1C(=O)C1=C(O)C=C(O)C=C1)C1=CC=CC=C1C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-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
25058141
PubChem Substance
99444913
ChemSpider
24694529
ChEMBL
CHEMBL470365
HET
PY9
PDB Entries
3ekr

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 Solubility0.0769 mg/mLALOGPS
logP2.79ALOGPS
logP4.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.02ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.76 m3·mol-1ChemAxon
Polarizability30.73 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+0.9049
Caco-2 permeable+0.6105
P-glycoprotein substrateNon-substrate0.5183
P-glycoprotein inhibitor INon-inhibitor0.9075
P-glycoprotein inhibitor IINon-inhibitor0.7234
Renal organic cation transporterNon-inhibitor0.5728
CYP450 2C9 substrateNon-substrate0.6637
CYP450 2D6 substrateNon-substrate0.6792
CYP450 3A4 substrateSubstrate0.6015
CYP450 1A2 substrateNon-inhibitor0.5062
CYP450 2C9 inhibitorNon-inhibitor0.6206
CYP450 2D6 inhibitorNon-inhibitor0.6372
CYP450 2C19 inhibitorNon-inhibitor0.6204
CYP450 3A4 inhibitorNon-inhibitor0.8497
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6346
Ames testNon AMES toxic0.7614
CarcinogenicityNon-carcinogens0.9031
BiodegradationNot ready biodegradable0.7922
Rat acute toxicity2.6117 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9646
hERG inhibition (predictor II)Inhibitor0.5733
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Salicylamides / Benzamides / Benzoyl derivatives / N-acylpyrrolidines / Resorcinols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Toluenes / Pyrroles / Vinylogous acids
show 7 more
Substituents
2-phenylpyrrolidine / Salicylamide / Salicylic acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzoyl / N-acylpyrrolidine / Resorcinol / Toluene / 1-hydroxy-4-unsubstituted benzenoid
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tpr domain binding
Specific Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
Gene Name
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 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 15:31 / Updated on December 01, 2017 16:04