N-(4-Chlorobenzyl)-2-(4-ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)acetamide

ID: ALA3407691

PubChem CID: 53244723

Max Phase: Preclinical

Molecular Formula: C17H23ClN2O3

Molecular Weight: 338.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CC(C)(C)OC(=O)C1CC(=O)NCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C17H23ClN2O3/c1-4-20-11-17(2,3)23-16(22)14(20)9-15(21)19-10-12-5-7-13(18)8-6-12/h5-8,14H,4,9-11H2,1-3H3,(H,19,21)

Standard InChI Key:  YFEFXZMGVVLTDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.3238   -0.1256    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
    1.2709   -1.9497    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 O   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    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
   -3.8933    3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.5994    0.0000 C   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
   -5.1894    6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895    7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4885    8.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7876    7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7876    6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4886    5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8268    8.1110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
  4  8  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3407691

   N-(4-Chlorobenzyl)-2-(4-ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)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: 338.84

Molecular Weight (Monoisotopic): 338.1397

AlogP: 2.37

#Rotatable Bonds: 5

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.27

CX LogP: 2.37

CX LogD: 2.34

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.53

References

1. Bardiot D, Thevissen K, De Brucker K, Peeters A, Cos P, Taborda CP, McNaughton M, Maes L, Chaltin P, Cammue BP, Marchand A..  (2015)  2-(2-oxo-morpholin-3-yl)-acetamide derivatives as broad-spectrum antifungal agents.,  58  (3): [PMID:25585716] [10.1021/jm501814x]

Source

Source(1):

• Scientific Literature