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

ID: ALA3246950

Cas Number: 22953-54-4

PubChem CID: 89925

Max Phase: Preclinical

Molecular Formula: C17H16Cl3NO2

Molecular Weight: 372.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Oc1ccc(N(CCCl)CCCl)cc1)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C17H16Cl3NO2/c18-8-10-21(11-9-19)15-4-6-16(7-5-15)23-17(22)13-2-1-3-14(20)12-13/h1-7,12H,8-11H2

Standard InChI Key:  SXYLQUYLIISZOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.5521  -14.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510  -15.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590  -15.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9687  -15.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659  -14.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572  -14.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2588  -16.7386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510  -17.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664  -17.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9662  -17.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508  -17.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430  -18.3726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6738  -18.3733    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2548  -13.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613  -13.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9588  -12.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6702  -13.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672  -11.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6651  -11.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9556  -10.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2468  -11.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524  -11.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3718  -10.6059    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
  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
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246950

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

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: 372.68

Molecular Weight (Monoisotopic): 371.0247

AlogP: 4.84

#Rotatable Bonds: 7

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.38

CX LogP: 5.68

CX LogD: 5.68

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.40

Np Likeness Score: -0.99

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