2-(4-Ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)-N-(4-isopropylphenyl)acetamide

ID: ALA3407652

PubChem CID: 53244396

Max Phase: Preclinical

Molecular Formula: C19H28N2O3

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CC(C)(C)OC(=O)C1CC(=O)Nc1ccc(C(C)C)cc1

Standard InChI:  InChI=1S/C19H28N2O3/c1-6-21-12-19(4,5)24-18(23)16(21)11-17(22)20-15-9-7-14(8-10-15)13(2)3/h7-10,13,16H,6,11-12H2,1-5H3,(H,20,22)

Standard InChI Key:  QPLWIEGBKHLNPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  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
    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
   -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
   -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
   -2.5844    7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    9.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8304   10.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9086   10.3641    0.0000 C   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
  8 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3407652

   2-(4-Ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)-N-(4-isopropylphenyl)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: 332.44

Molecular Weight (Monoisotopic): 332.2100

AlogP: 3.16

#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: 6.15

CX LogP: 3.30

CX LogD: 3.28

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.52

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