4-(bis(2-chloroethyl)amino)phenyl 3-nitrobenzoate

ID: ALA3246954

Cas Number: 22953-58-8

PubChem CID: 89929

Max Phase: Preclinical

Molecular Formula: C17H16Cl2N2O4

Molecular Weight: 383.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Oc1ccc(N(CCCl)CCCl)cc1)c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H16Cl2N2O4/c18-8-10-20(11-9-19)14-4-6-16(7-5-14)25-17(22)13-2-1-3-15(12-13)21(23)24/h1-7,12H,8-11H2

Standard InChI Key:  OTCCTHBQSGSBNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   17.3371  -15.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3359  -15.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0440  -16.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7536  -15.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7508  -15.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0422  -14.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0438  -17.0853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3360  -17.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7514  -17.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7512  -18.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3358  -18.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6280  -18.7193    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.4588  -18.7200    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0397  -13.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7462  -13.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7438  -12.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4552  -13.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4521  -12.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4500  -11.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7406  -10.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0317  -11.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0373  -12.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1601  -10.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1580  -10.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8688  -11.3556    0.0000 O   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
  3  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 10 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 23 24  2  0
 23 25  1  0
 19 23  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3246954

   p-(Bis(2-chloroethyl)amino)phenyl m-nitrobenzoate

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: 383.23

Molecular Weight (Monoisotopic): 382.0487

AlogP: 4.10

#Rotatable Bonds: 8

Polar Surface Area: 72.68

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.38

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.23

Np Likeness Score: -1.16

References

1. Panthananickal A, Hansch C, Leo A..  (1978)  Structure-activity relationships in antitumor aniline mustards.,  21  (1): [PMID:619146] [10.1021/jm00199a004]

Source

Source(1):

• Scientific Literature