2-Amino-9,10-dimethyl-9,10-dihydroindolo[2,3-a]pyrimido[5,4-c]carbazol-4(3H)-one

ID: ALA2089147

PubChem CID: 136217466

Max Phase: Preclinical

Molecular Formula: C22H17N5O

Molecular Weight: 367.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2ccccc2c2c3nc(N)[nH]c(=O)c3c3c4ccccc4n(C)c3c21

Standard InChI:  InChI=1S/C22H17N5O/c1-26-13-9-5-3-7-11(13)15-17-18(24-22(23)25-21(17)28)16-12-8-4-6-10-14(12)27(2)20(16)19(15)26/h3-10H,1-2H3,(H3,23,24,25,28)

Standard InChI Key:  CGXNLGCIRYNXHX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 33  0  0  0  0  0  0  0  0999 V2000
   -0.3230  -14.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864  -15.7030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677  -15.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785  -14.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201  -15.7012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844  -14.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648  -15.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149  -15.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853  -15.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006  -14.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502  -14.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8723  -15.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845  -14.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4483  -14.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001  -14.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841  -15.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194  -15.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9485  -16.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739  -13.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400  -13.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276  -12.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445  -12.2143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784  -12.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9954  -12.9412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961  -11.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046  -12.9343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604  -16.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7397  -15.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  2  0
 12 13  2  0
  4 13  1  0
 13 14  1  0
 12  5  1  0
 14 15  2  0
  5  3  1  0
 15 16  1  0
  1 20  1  0
 16 17  2  0
 17 12  1  0
 28  2  1  0
  5 18  1  0
 19 20  2  0
  6  7  2  0
  2  7  1  0
  7  8  1  0
  6  1  1  0
  8  9  2  0
  3  4  2  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  9 10  1  0
 23 25  1  0
 19  4  1  0
 21 26  2  0
 10 11  2  0
  2 27  1  0
 11  6  1  0
  3 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089147

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.41

Molecular Weight (Monoisotopic): 367.1433

AlogP: 3.80

#Rotatable Bonds: ┄

Polar Surface Area: 81.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.20

CX Basic pKa: 3.35

CX LogP: 3.18

CX LogD: 3.18

Aromatic Rings: 6

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.13

References

1. Pierce LT, Cahill MM, Winfield HJ, McCarthy FO..  (2012)  Synthesis and identification of novel indolo[2,3-a]pyrimido[5,4-c]carbazoles as a new class of anti-cancer agents.,  56  [PMID:22910137] [10.1016/j.ejmech.2012.08.002]

Source

Source(1):

• Scientific Literature