2-acetyl-4-(4-(dimethylamino)phenyl)indeno[2,1-e]pyrrolo[2,3-b]pyridin-5(1H)-one

ID: ALA4475411

PubChem CID: 129908047

Max Phase: Preclinical

Molecular Formula: C24H19N3O2

Molecular Weight: 381.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)c1cc2c(-c3ccc(N(C)C)cc3)c3c(nc2[nH]1)-c1ccccc1C3=O

Standard InChI:  InChI=1S/C24H19N3O2/c1-13(28)19-12-18-20(14-8-10-15(11-9-14)27(2)3)21-22(26-24(18)25-19)16-6-4-5-7-17(16)23(21)29/h4-12H,1-3H3,(H,25,26)

Standard InChI Key:  WANWGZTZQXJMJU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   13.2484  -17.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5027  -17.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8398  -16.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4312  -17.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1814  -17.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3863  -16.9993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8892  -18.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0947  -18.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8396  -17.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4367  -18.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7749  -18.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0251  -17.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4790  -17.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6826  -17.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4352  -17.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9830  -18.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1421  -19.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5947  -19.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8480  -20.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6484  -20.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1950  -20.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9388  -19.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4400  -19.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2803  -16.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8868  -17.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4513  -16.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9033  -21.6522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3584  -22.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7032  -21.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  2  0
  2  3  1  0
  3  5  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 10  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  7 17  1  0
 10 23  2  0
  2 24  1  0
 24 25  1  0
 24 26  2  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475411

   ---

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: 381.44

Molecular Weight (Monoisotopic): 381.1477

AlogP: 4.71

#Rotatable Bonds: 3

Polar Surface Area: 66.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.58

CX Basic pKa: 4.46

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.25

References

1. Stanton RA, Lu X, Detorio M, Montero C, Hammond ET, Ehteshami M, Domaoal RA, Nettles JH, Feraud M, Schinazi RF..  (2016)  Discovery, characterization, and lead optimization of 7-azaindole non-nucleoside HIV-1 reverse transcriptase inhibitors.,  26  (16): [PMID:27390064] [10.1016/j.bmcl.2016.06.065]

Source

Source(1):

• Scientific Literature