N-[2-(2-Dimethylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-10-yl]-2,2-dimethyl-propionamide

ID: ALA356939

PubChem CID: 10364662

Max Phase: Preclinical

Molecular Formula: C25H27N3O3

Molecular Weight: 417.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1C(=O)c2cccc3cc4ccc(NC(=O)C(C)(C)C)cc4c(c23)C1=O

Standard InChI:  InChI=1S/C25H27N3O3/c1-25(2,3)24(31)26-17-10-9-15-13-16-7-6-8-18-20(16)21(19(15)14-17)23(30)28(22(18)29)12-11-27(4)5/h6-10,13-14H,11-12H2,1-5H3,(H,26,31)

Standard InChI Key:  DDPVQBZDHSMXPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.0625   -4.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -6.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -5.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -7.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -4.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -5.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -7.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  3  1  0
  7  4  1  0
  8 12  1  0
  9  5  1  0
 10  7  1  0
 11  1  1  0
 12 18  1  0
 13  9  2  0
 14  2  2  0
 15  8  1  0
 16  7  2  0
 17  3  2  0
 18 16  1  0
 19  8  2  0
 20 10  2  0
 21 11  1  0
 22 21  1  0
 23  6  2  0
 24 18  2  0
 25 26  2  0
 26 23  1  0
 27 15  1  0
 28 15  1  0
 29 15  1  0
 30 22  1  0
 31 22  1  0
  5  4  2  0
  9 25  1  0
 13 10  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA356939

   N-[15-[2-(dimethylamino)ethyl]-14,16-dioxo-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,8,10,12-heptaen-4-yl]-2,2-dimethylpropanamide

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: 417.51

Molecular Weight (Monoisotopic): 417.2052

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 69.72

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.73

CX Basic pKa: 8.52

CX LogP: 3.95

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -0.93

References

1. Sami SM, Dorr RT, Alberts DS, Sólyom AM, Remers WA..  (1996)  2-[2'-(Dimethylamino)ethyl]-1,2-dihydro- 3H-dibenz[de,h]isoquinoline-1,3-diones with substituents at positions 4, 8, 9, 10, and 11. Synthesis, antitumor activity, and quantitative structure-activity relationships.,  39  (25): [PMID:8960558] [10.1021/jm960623g]

2. Sami SM, Dorr RT, Sólyom AM, Alberts DS, Remers WA..  (1995)  Amino-substituted 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H- dibenz[de,h]isoquinoline-1,3-diones. Synthesis, antitumor activity, and quantitative structure--activity relationship.,  38  (6): [PMID:7699715] [10.1021/jm00006a018]

Source

Source(1):

• Scientific Literature