6-[(3S)-pyrrolidin-3-yl]oxy-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)isoquinoline

ID: ALA4644763

PubChem CID: 156018126

Max Phase: Preclinical

Molecular Formula: C20H18N4O

Molecular Weight: 330.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1cc2cc(-c3cncc4ccc(O[C@H]5CCNC5)cc34)cnc2[nH]1

Standard InChI:  InChI=1S/C20H18N4O/c1-2-16(25-17-4-5-21-11-17)8-18-14(1)9-22-12-19(18)15-7-13-3-6-23-20(13)24-10-15/h1-3,6-10,12,17,21H,4-5,11H2,(H,23,24)/t17-/m0/s1

Standard InChI Key:  QAVZVAORORKNHF-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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   19.8404   -7.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1265   -7.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1265   -8.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8431   -9.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5506   -8.7559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5506   -7.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4070   -9.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6885   -8.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6901   -7.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4038   -7.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9760   -7.5226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2578   -7.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1720   -8.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3636   -8.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9528   -8.2141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5049   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8404   -6.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1272   -6.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1283   -5.4566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8419   -5.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5515   -5.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5582   -6.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1598   -4.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8262   -4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0088   -4.2428    0.0000 N   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
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 21 23  1  0
 24 23  2  0
 25 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644763

   ---

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: 330.39

Molecular Weight (Monoisotopic): 330.1481

AlogP: 3.52

#Rotatable Bonds: 3

Polar Surface Area: 62.83

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.29

CX LogP: 2.07

CX LogD: -0.67

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -0.15

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]

2. de Esch IJP, Erlanson DA, Jahnke W, Johnson CN, Walsh L..  (2022)  Fragment-to-Lead Medicinal Chemistry Publications in 2020.,  65  (1.0): [PMID:34928151] [10.1021/acs.jmedchem.1c01803]

Source

Source(1):

• Scientific Literature