2-{N,N-bis(2'-chloroethyl)}aminoacetamido-4'-chloro-5-nitrobenzophenone

ID: ALA2282317

PubChem CID: 72722182

Max Phase: Preclinical

Molecular Formula: C19H18Cl3N3O4

Molecular Weight: 458.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(CCCl)CCCl)Nc1ccc([N+](=O)[O-])cc1C(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H18Cl3N3O4/c20-7-9-24(10-8-21)12-18(26)23-17-6-5-15(25(28)29)11-16(17)19(27)13-1-3-14(22)4-2-13/h1-6,11H,7-10,12H2,(H,23,26)

Standard InChI Key:  VWXDADBWBNLOFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   10.8945  -10.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8933  -11.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6014  -11.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3110  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3082  -10.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5996  -10.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0144  -10.3242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0113   -9.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7174   -9.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020   -9.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4267   -9.5016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1329   -9.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8421   -9.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5483   -9.0850    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4298  -10.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1390  -10.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8452  -10.3135    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0194  -11.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7264  -11.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0207  -12.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3123  -13.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3132  -14.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0221  -14.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7315  -14.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7271  -13.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1834  -11.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1827  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4760  -11.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0245  -15.2328    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
  4 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
  2 26  1  0
 23 29  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2282317

   2-[bis(2-chloroethyl)amino]-N-[2-(4-chlorobenzoyl)-4-nitrophenyl]acetamide

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: 458.73

Molecular Weight (Monoisotopic): 457.0363

AlogP: 4.20

#Rotatable Bonds: 10

Polar Surface Area: 92.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.99

CX Basic pKa: 3.46

CX LogP: 5.08

CX LogD: 5.08

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -1.69

References

1. Singh RK, Prasad DN, Bhardwaj TR.  (2013)  Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent,  22  (12): [10.1007/s00044-013-0582-8]

Source

Source(1):

• Scientific Literature