4-(2-((4-Chlorobenzyl)amino)-2-oxoethoxy)-N-(2,3-dimethylphenyl)benzamide

ID: ALA4877493

PubChem CID: 164628020

Max Phase: Preclinical

Molecular Formula: C24H23ClN2O3

Molecular Weight: 422.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(NC(=O)c2ccc(OCC(=O)NCc3ccc(Cl)cc3)cc2)c1C

Standard InChI:  InChI=1S/C24H23ClN2O3/c1-16-4-3-5-22(17(16)2)27-24(29)19-8-12-21(13-9-19)30-15-23(28)26-14-18-6-10-20(25)11-7-18/h3-13H,14-15H2,1-2H3,(H,26,28)(H,27,29)

Standard InChI Key:  KIMYHBVSJRISDQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.7455  -18.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552  -17.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552  -16.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438  -16.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387  -16.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387  -17.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313  -16.5853    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1636  -18.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706  -17.8127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790  -18.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2860  -17.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944  -18.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7015  -17.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4070  -18.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1127  -17.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1127  -16.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3994  -16.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7015  -16.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8192  -16.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8192  -15.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5281  -16.9848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2346  -16.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9407  -16.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6467  -16.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6467  -15.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9309  -15.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2346  -15.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3554  -16.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9407  -17.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790  -19.0374    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
  6  5  2  0
  6  1  1  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
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 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 24 28  1  0
 23 29  1  0
 10 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877493

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 422.91

Molecular Weight (Monoisotopic): 422.1397

AlogP: 4.90

#Rotatable Bonds: 7

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: ┄

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.75

References

1. Turgutalp B, Uslu M, Helvacioglu S, Charehsaz M, Gurdal EE, Sippl W, Kocabas F, Yarim M..  (2021)  Lead Optimization and Structure-Activity Relationship Studies on Myeloid Ecotropic Viral Integration Site 1 Inhibitor.,  64  (19.0): [PMID:34542289] [10.1021/acs.jmedchem.1c00972]

Source

Source(1):

• Scientific Literature