2-[6-[(3S)-pyrrolidin-3-yl]oxy-4-isoquinolyl]-1,3-benzoxazole

ID: ALA4649466

PubChem CID: 156022109

Max Phase: Preclinical

Molecular Formula: C20H17N3O2

Molecular Weight: 331.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1ccc2oc(-c3cncc4ccc(O[C@H]5CCNC5)cc34)nc2c1

Standard InChI:  InChI=1S/C20H17N3O2/c1-2-4-19-18(3-1)23-20(25-19)17-12-22-10-13-5-6-14(9-16(13)17)24-15-7-8-21-11-15/h1-6,9-10,12,15,21H,7-8,11H2/t15-/m0/s1

Standard InChI Key:  JERKDFMIYNHLMR-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    6.8687   -7.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548   -8.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548   -9.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8713   -9.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5829   -9.1954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5829   -8.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396   -9.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211   -9.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186   -8.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -7.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046   -7.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -8.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2007   -9.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -9.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816   -8.6494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337   -8.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8687   -7.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -6.6488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4583   -5.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2833   -5.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5351   -6.6488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6959   -5.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2797   -4.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4607   -4.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462   -5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 10  1  0
  9 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 17  1  1  0
 18 17  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4649466

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.38

Molecular Weight (Monoisotopic): 331.1321

AlogP: 3.78

#Rotatable Bonds: 3

Polar Surface Area: 60.18

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.29

CX LogP: 2.54

CX LogD: -0.19

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.59

References

1. Atobe M, Serizawa T, Yamakawa N, Takaba K, Nagano Y, Yamaura T, Tanaka E, Tazumi A, Bito S, Ishiguro M, Kawanishi M..  (2020)  Discovery of 4,6- and 5,7-Disubstituted Isoquinoline Derivatives as a Novel Class of Protein Kinase C ζ Inhibitors with Fragment-Merging Strategy.,  63  (13): [PMID:32551607] [10.1021/acs.jmedchem.0c00449]

Source

Source(1):

• Scientific Literature