Ethyl 4-(2-(2-acetamidophenyl)-2-oxoacetamido)benzoate

ID: ALA3577034

PubChem CID: 122177417

Max Phase: Preclinical

Molecular Formula: C19H18N2O5

Molecular Weight: 354.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(NC(=O)C(=O)c2ccccc2NC(C)=O)cc1

Standard InChI:  InChI=1S/C19H18N2O5/c1-3-26-19(25)13-8-10-14(11-9-13)21-18(24)17(23)15-6-4-5-7-16(15)20-12(2)22/h4-11H,3H2,1-2H3,(H,20,22)(H,21,24)

Standard InChI Key:  MUEWXKPDASKSLU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876   -6.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1824   -7.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5843   -7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8725   -9.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691  -10.5028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9086  -10.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608  -12.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186  -12.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    3.6021    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
  4  7  1  0
  7  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
 21 23  2  0
 18 21  1  0
 22 24  1  0
 24 25  1  0
  8 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577034

   ---

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: 354.36

Molecular Weight (Monoisotopic): 354.1216

AlogP: 2.64

#Rotatable Bonds: 6

Polar Surface Area: 101.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.11

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -1.09

References

1. El-Faham A, Zainab Al Marhoon, Abdel-Megeed A, Khattab SN, Bekhit AA, Albericio F..  (2014)  α-Ketoamino acid ester derivatives as promising MAO inhibitors.,  25  (1): [PMID:25466194] [10.1016/j.bmcl.2014.11.007]

Source

Source(1):

• Scientific Literature