2-(5-nitro-1,3-dioxoisoindolin-2-yl)-N-(4-(2-oxopropoxy)phenyl)acetamide

ID: ALA604486

PubChem CID: 46225803

Max Phase: Preclinical

Molecular Formula: C19H15N3O7

Molecular Weight: 397.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)COc1ccc(NC(=O)CN2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)cc1

Standard InChI:  InChI=1S/C19H15N3O7/c1-11(23)10-29-14-5-2-12(3-6-14)20-17(24)9-21-18(25)15-7-4-13(22(27)28)8-16(15)19(21)26/h2-8H,9-10H2,1H3,(H,20,24)

Standard InChI Key:  NZGKLOLOFAPWKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.2473   -4.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484   -5.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -6.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -4.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200   -4.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8152   -5.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0277   -5.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -5.3104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -4.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -3.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318   -6.7650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -5.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -4.4962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6769   -4.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -3.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -4.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5125   -4.5838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708   -3.8767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5179   -6.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340   -6.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7598   -6.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1679   -5.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496   -5.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1775   -7.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -7.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -8.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2451   -8.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0128   -8.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 13 15  1  0
  1 13  1  0
  5  4  2  0
 12 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 16 18  2  0
  8  9  1  0
 17 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  2  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  7 11  2  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
  8 12  1  0
 25 26  1  0
  2  3  1  0
 26 27  1  0
  3  6  2  0
 27 28  1  0
  1  2  2  0
 27 29  2  0
M  CHG  2  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA604486

   2-(5-nitro-1,3-dioxoisoindol-2-yl)-N-[4-(2-oxopropoxy)phenyl]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: 397.34

Molecular Weight (Monoisotopic): 397.0910

AlogP: 1.80

#Rotatable Bonds: 7

Polar Surface Area: 135.92

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.18

CX Basic pKa: ┄

CX LogP: 1.42

CX LogD: 1.42

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.65

References

1. Fells JI, Tsukahara R, Liu J, Tigyi G, Parrill AL..  (2009)  Structure-based drug design identifies novel LPA3 antagonists.,  17  (21): [PMID:19800804] [10.1016/j.bmc.2009.09.022]

Source

Source(1):

• Scientific Literature