8-Methoxy-acridine-4-carboxylic acid (2-dimethylamino-ethyl)-amide hydrochloride

ID: ALA1203698

PubChem CID: 386511

Max Phase: Preclinical

Molecular Formula: C19H22ClN3O2

Molecular Weight: 323.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2nc3c(C(=O)NCCN(C)C)cccc3cc12.Cl

Standard InChI:  InChI=1S/C19H21N3O2.ClH/c1-22(2)11-10-20-19(23)14-7-4-6-13-12-15-16(21-18(13)14)8-5-9-17(15)24-3;/h4-9,12H,10-11H2,1-3H3,(H,20,23);1H

Standard InChI Key:  BSZAYAHSZXNOJI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    9.0495   -2.2475    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6410    3.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    3.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752   -3.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150   -3.7418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270   -5.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323   -5.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2443   -7.4841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2879   -8.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2097   -8.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 16 17  2  0
 17  4  1  0
 17  8  1  0
 11 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

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: 323.40

Molecular Weight (Monoisotopic): 323.1634

AlogP: 2.69

#Rotatable Bonds: 5

Polar Surface Area: 54.46

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.51

CX LogP: 2.44

CX LogD: 1.30

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -1.12

References

1. Atwell GJ, Rewcastle GW, Baguley BC, Denny WA..  (1987)  Potential antitumor agents. 50. In vivo solid-tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide.,  30  (4): [PMID:3560161] [10.1021/jm00387a014]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays