5-(4-((3-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)methyl)piperazin-1-yl)-N-methylpicolinamide

ID: ALA4874589

PubChem CID: 155587004

Max Phase: Preclinical

Molecular Formula: C22H26N6O2

Molecular Weight: 406.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc2cnc(CN3CCN(c4ccc(C(=O)NC)nc4)CC3)cc2[nH]c1=O

Standard InChI:  InChI=1S/C22H26N6O2/c1-3-15-10-16-12-24-17(11-20(16)26-21(15)29)14-27-6-8-28(9-7-27)18-4-5-19(25-13-18)22(30)23-2/h4-5,10-13H,3,6-9,14H2,1-2H3,(H,23,30)(H,26,29)

Standard InChI Key:  KQWMSOMOYSGKJA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.9947   -5.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111   -4.7637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7081   -3.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -3.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800   -4.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842   -3.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737   -3.5219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8546   -3.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505   -4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -5.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429   -3.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336   -5.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218   -4.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210   -3.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369   -3.9279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1374   -4.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8492   -5.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5645   -4.7526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5633   -3.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8470   -3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763   -5.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2749   -5.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9884   -6.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7038   -5.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7012   -5.1585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9870   -4.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4207   -6.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4218   -7.2228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344   -5.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1367   -7.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
  9 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 27 28  1  0
 27 29  2  0
 24 27  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874589

   ---

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: 406.49

Molecular Weight (Monoisotopic): 406.2117

AlogP: 1.56

#Rotatable Bonds: 5

Polar Surface Area: 94.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 6.62

CX LogP: 1.22

CX LogD: 1.16

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -1.49

References

1. Sabnis RW..  (2021)  Novel Azaquinolones as PARP1 Inhibitors for Treating Cancer.,  12  (4.0): [PMID:33859786] [10.1021/acsmedchemlett.1c00122]

2. Johannes JW, Balazs A, Barratt D, Bista M, Chuba MD, Cosulich S, Critchlow SE, Degorce SL, Di Fruscia P, Edmondson SD, Embrey K, Fawell S, Ghosh A, Gill SJ, Gunnarsson A, Hande SM, Heightman TD, Hemsley P, Illuzzi G, Lane J, Larner C, Leo E, Liu L, Madin A, Martin S, McWilliams L, O'Connor MJ, Orme JP, Pachl F, Packer MJ, Pei X, Pike A, Schimpl M, She H, Staniszewska AD, Talbot V, Underwood E, Varnes JG, Xue L, Yao T, Zhang K, Zhang AX, Zheng X..  (2021)  Discovery of 5-{4-[(7-Ethyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)methyl]piperazin-1-yl}-N-methylpyridine-2-carboxamide (AZD5305): A PARP1-DNA Trapper with High Selectivity for PARP1 over PARP2 and Other PARPs.,  64  (19.0): [PMID:34570508] [10.1021/acs.jmedchem.1c01012]

Source

Source(1):

• Scientific Literature