1-(1-(2-Chlorobenzoyl)piperidin-4-yl)-8,9-dihydro-2,4,7,9a-tetraazabenzo[cd]azulen-6(7H)-one

ID: ALA4532640

PubChem CID: 155547387

Max Phase: Preclinical

Molecular Formula: C21H20ClN5O2

Molecular Weight: 409.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NCCn2c(C3CCN(C(=O)c4ccccc4Cl)CC3)nc3cncc1c32

Standard InChI:  InChI=1S/C21H20ClN5O2/c22-16-4-2-1-3-14(16)21(29)26-8-5-13(6-9-26)19-25-17-12-23-11-15-18(17)27(19)10-7-24-20(15)28/h1-4,11-13H,5-10H2,(H,24,28)

Standard InChI Key:  QWHBOKIAPQHJQG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    8.8404   -7.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3561   -7.7262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5789   -7.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5789   -6.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8698   -6.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7789   -5.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3573   -4.8485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1704   -4.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6143   -5.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3561   -6.3997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1566   -6.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1566   -7.4716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8698   -7.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037   -5.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3002   -7.0630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8916   -7.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0703   -7.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6617   -7.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0703   -6.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8916   -6.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1215   -7.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5301   -6.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5301   -7.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1178   -8.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5257   -9.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3449   -9.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7546   -8.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3443   -7.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7511   -7.0616    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 10  1  0
  4 10  1  0
 11 12  2  0
 12 13  1  0
  3 13  2  0
  5 11  1  0
  6 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 21 22  2  0
 21 23  1  0
 15 21  1  0
  1 18  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532640

   ---

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: 409.88

Molecular Weight (Monoisotopic): 409.1306

AlogP: 2.85

#Rotatable Bonds: 2

Polar Surface Area: 80.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.14

CX LogP: 1.46

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -1.24

References

1. Li H, Hu Y, Wang X, He G, Xu Y, Zhu Q..  (2016)  Novel tricyclic poly (ADP-ribose) polymerase-1/2 inhibitors with potent anticancer chemopotentiating activity: Design, synthesis and biological evaluation.,  24  (19): [PMID:27561983] [10.1016/j.bmc.2016.08.016]

Source

Source(1):

• Scientific Literature