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

ID: ALA4515565

PubChem CID: 155539891

Max Phase: Preclinical

Molecular Formula: C21H23N5O

Molecular Weight: 361.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NCCn2c(C3CCN(Cc4ccccc4)CC3)nc3cncc1c32

Standard InChI:  InChI=1S/C21H23N5O/c27-21-17-12-22-13-18-19(17)26(11-8-23-21)20(24-18)16-6-9-25(10-7-16)14-15-4-2-1-3-5-15/h1-5,12-13,16H,6-11,14H2,(H,23,27)

Standard InChI Key:  ZEXCKQPPOYSAKB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   11.0511  -10.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5853  -11.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7998  -11.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804  -10.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0618   -9.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9532   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5212   -8.5068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3383   -8.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7930   -9.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5529  -10.0415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3586  -10.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3781  -11.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0966  -11.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759   -8.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5100  -10.6382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1173  -11.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2963  -11.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8721  -10.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2648   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0858   -9.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3310  -10.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7552  -11.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3584  -12.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7863  -12.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6111  -12.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0080  -12.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5800  -11.2999    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  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  1  0
 15 21  1  0
  1 18  1  0
 22 23  1  0
 22 27  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4515565

   ---

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: 361.45

Molecular Weight (Monoisotopic): 361.1903

AlogP: 2.55

#Rotatable Bonds: 3

Polar Surface Area: 63.05

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.11

CX LogP: 1.50

CX LogD: -0.21

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.95

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