11-Acetyl-2-(2-dimethylamino-ethyl)-dibenzo[de,h]isoquinoline-1,3-dione

ID: ALA147668

PubChem CID: 44364118

Max Phase: Preclinical

Molecular Formula: C22H20N2O3

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1cccc2cc3cccc4c3c(c12)C(=O)N(CCN(C)C)C4=O

Standard InChI:  InChI=1S/C22H20N2O3/c1-13(25)16-8-4-6-14-12-15-7-5-9-17-19(15)20(18(14)16)22(27)24(21(17)26)11-10-23(2)3/h4-9,12H,10-11H2,1-3H3

Standard InChI Key:  ZMOIOXCNUGUANF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  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
    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
    1.9375   -5.8417    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
    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
    5.4917   -4.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -4.6042    0.0000 O   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
    4.7875   -7.4875    0.0000 C   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
    1.2167   -6.2417    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
    1.2167   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -4.3000    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  5  1  0
  9  7  1  0
 10  7  2  0
 11  1  1  0
 12  8  2  0
 13  2  2  0
 14  3  2  0
 15 10  1  0
 16 15  2  0
 17 11  1  0
 18 17  1  0
 19  6  2  0
 20 23  2  0
 21  9  2  0
 22 10  1  0
 23 19  1  0
 24 22  2  0
 25 15  1  0
 26 18  1  0
 27 18  1  0
  5  4  2  0
  8 20  1  0
 12  9  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA147668

   3-Acetyl-15-[2-(dimethylamino)ethyl]-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,8,10,12-heptaene-14,16-dione

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: 360.41

Molecular Weight (Monoisotopic): 360.1474

AlogP: 3.35

#Rotatable Bonds: 4

Polar Surface Area: 57.69

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.82

CX LogP: 2.47

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.41

Np Likeness Score: -0.57

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]

Source

Source(1):

• Scientific Literature