5-(pyrrolidin-1-ylmethyl)quinolin-8-ol

ID: ALA5203096

Cas Number: 41455-82-7

PubChem CID: 776032

Max Phase: Preclinical

Molecular Formula: C14H16N2O

Molecular Weight: 228.29

Names and Identifiers

Canonical SMILES:  Oc1ccc(CN2CCCC2)c2cccnc12

Standard InChI:  InChI=1S/C14H16N2O/c17-13-6-5-11(10-16-8-1-2-9-16)12-4-3-7-15-14(12)13/h3-7,17H,1-2,8-10H2

Standard InChI Key:  YIDLQDBGBKKOGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   -0.6497   -0.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    0.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -0.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666   -1.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6497   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666   -2.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3653   -1.5310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830   -1.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848   -0.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704    0.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    1.3600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    2.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5328    1.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  5  7  1  0
  6  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
  1 11  1  0
  2 12  1  0
 12 13  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203096

   5-(Pyrrolidin-1-ylmethyl)quinolin-8-ol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 228.29

Molecular Weight (Monoisotopic): 228.1263

AlogP: 2.54

#Rotatable Bonds: 2

Polar Surface Area: 36.36

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.36

CX Basic pKa: 9.62

CX LogP: 1.31

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.86

Np Likeness Score: -0.94

References

1. Pape VFS, Palkó R, Tóth S, Szabó MJ, Sessler J, Dormán G, Enyedy ÉA, Soós T, Szatmári I, Szakács G..  (2022)  Structure-Activity Relationships of 8-Hydroxyquinoline-Derived Mannich Bases with Tertiary Amines Targeting Multidrug-Resistant Cancer.,  65  (11.0): [PMID:35613553] [10.1021/acs.jmedchem.2c00076]

Source

Source(1):

• Scientific Literature