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Identification
Name4-{[(2R)-2-(2-methylphenyl)pyrrolidin-1-yl]carbonyl}benzene-1,3-diol
Accession NumberDB08442
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 297.3484
Monoisotopic: 297.136493479
Chemical FormulaC18H19NO3
InChI KeyTWODFUZHWYZBHZ-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][C@@]1(CCCN1C(=O)C1=C(O)C=C(O)C=C1)C1=CC=CC=C1C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
Alternative Parents
Substituents
  • 2-phenylpyrrolidine
  • Salicylic acid or derivatives
  • Salicylamide
  • Benzoic acid or derivatives
  • Benzamide
  • Resorcinol
  • N-acylpyrrolidine
  • Benzoyl
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Pyrrole
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.6206
CYP450 2D6 substrateNon-inhibitor0.6372
CYP450 2C19 substrateNon-inhibitor0.6204
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Heat shock protein HSP 90-alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Heat shock protein HSP 90-alpha P07900 Details

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

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Drug created on September 15, 2010 15:31 / Updated on September 16, 2013 18:09