4-(bis(2-chloroethyl)amino)phenyl 4-methoxybenzoate

ID: ALA3246953

Cas Number: 22953-57-7

PubChem CID: 89928

Max Phase: Preclinical

Molecular Formula: C18H19Cl2NO3

Molecular Weight: 368.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)Oc2ccc(N(CCCl)CCCl)cc2)cc1

Standard InChI:  InChI=1S/C18H19Cl2NO3/c1-23-16-6-2-14(3-7-16)18(22)24-17-8-4-15(5-9-17)21(12-10-19)13-11-20/h2-9H,10-13H2,1H3

Standard InChI Key:  HYSSJKYEXPISGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   13.5978  -15.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5967  -16.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3047  -16.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0144  -16.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0115  -15.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3029  -14.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3045  -17.4526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5967  -17.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0121  -17.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0119  -18.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5965  -18.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8887  -19.0866    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7195  -19.0873    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3005  -14.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0070  -13.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0045  -12.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7159  -14.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7129  -12.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7108  -11.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0013  -11.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2925  -11.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2981  -12.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9978  -10.5058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7037  -10.0942    0.0000 C   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
 20 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246953

   p-(Bis(2-chloroethyl)amino)phenyl p-methoxybenzoate

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: 368.26

Molecular Weight (Monoisotopic): 367.0742

AlogP: 4.20

#Rotatable Bonds: 8

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.38

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: -0.59

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