rac-6-{3-[(3-aminopyrrolidin-1-yl)methyl]phenyl}isoquinolin-1-ol

ID: ALA5270570

Max Phase: Preclinical

Molecular Formula: C20H21N3O

Molecular Weight: 319.41

Names and Identifiers

Canonical SMILES:  NC1CCN(Cc2cccc(-c3ccc4c(O)nccc4c3)c2)C1

Standard InChI:  InChI=1S/C20H21N3O/c21-18-7-9-23(13-18)12-14-2-1-3-15(10-14)16-4-5-19-17(11-16)6-8-22-20(19)24/h1-6,8,10-11,18H,7,9,12-13,21H2,(H,22,24)

Standard InChI Key:  KJCKVXKGXLPESD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -4.2638    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5492    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5474   -1.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2638   -0.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097   -0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6951    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    1.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0225    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1637    0.6207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1637    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678    1.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    1.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    0.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638    1.0424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5474   -1.8545    0.0000 O   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
  6  5  2  0
  1  6  1  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
 11  8  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 15 17  1  0
 17 18  1  0
 19 18  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 18 22  1  0
 21 23  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5270570

   ---

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: 319.41

Molecular Weight (Monoisotopic): 319.1685

AlogP: 3.14

#Rotatable Bonds: 3

Polar Surface Area: 62.38

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.84

CX Basic pKa: 9.63

CX LogP: 2.78

CX LogD: 0.56

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -0.70

References

1. Müller J, Klein R, Tarkhanova O, Gryniukova A, Borysko P, Merkl S, Ruf M, Neumann A, Gastreich M, Moroz YS, Klebe G, Glinca S..  (2022)  Magnet for the Needle in Haystack: "Crystal Structure First" Fragment Hits Unlock Active Chemical Matter Using Targeted Exploration of Vast Chemical Spaces.,  65  (23.0): [PMID:36069712] [10.1021/acs.jmedchem.2c00813]

Source

Source(1):

• Scientific Literature