NAV

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

Identification

Generic Name
4-{[(2R)-2-(2-methylphenyl)pyrrolidin-1-yl]carbonyl}benzene-1,3-diol
DrugBank Accession Number
DB08442
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 297.3484
Monoisotopic: 297.136493479
Chemical Formula
C18H19NO3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-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
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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 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
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-phenylpyrrolidine / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Carboxamide group
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@]1(CCCN1C(=O)C1=C(O)C=C(O)C=C1)C1=CC=CC=C1C

References

General References
Not Available
PubChem Compound
25058141
PubChem Substance
99444913
ChemSpider
24694529
ChEMBL
CHEMBL470365
PDBe Ligand
PY9
PDB Entries
3ekr

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 Solubility0.0769 mg/mLALOGPS
logP2.79ALOGPS
logP4.02Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.02Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
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-MSsplash10-000i-0920000000-eefe343dd38b61268afa
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0490000000-c0f4265b83112c4dc42f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000b-0980000000-3b3c1b2d66078f6a605b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-4940000000-e0a18aef0107c4c4d10f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052s-1960000000-42d35798454e2bdf3454
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00e9-7910000000-f776600ade0720ffecc8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9430000000-e49485b5f308984fc017
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.09695
predicted
DeepCCS 1.0 (2019)
[M+H]+166.45496
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.23773
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Heat shock protein HSP 90-alpha
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52