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

ID: ALA2282316

PubChem CID: 76334409

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)c1ccccc1Cl

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

Standard InChI Key:  VBHSVZQBYURIDL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.9012  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001  -11.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081  -11.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178  -11.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3150  -10.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6063  -10.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211  -10.3365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0181   -9.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7242   -9.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -9.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335   -9.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1396   -9.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8489   -9.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5550   -9.0974    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4365  -10.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1458  -10.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8519  -10.3259    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0261  -11.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332  -11.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0274  -12.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191  -13.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200  -14.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289  -14.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383  -14.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7339  -13.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902  -11.9827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895  -12.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828  -11.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395  -12.7868    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
 25 29  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2282316

   2-[bis(2-chloroethyl)amino]-N-[2-(2-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: -1.74

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