2-(4-Ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)-N-(1-methyl-1H-indol-5-yl)acetamide

ID: ALA3407673

PubChem CID: 53244722

Max Phase: Preclinical

Molecular Formula: C19H25N3O3

Molecular Weight: 343.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CC(C)(C)OC(=O)C1CC(=O)Nc1ccc2c(ccn2C)c1

Standard InChI:  InChI=1S/C19H25N3O3/c1-5-22-12-19(2,3)25-18(24)16(22)11-17(23)20-14-6-7-15-13(10-14)8-9-21(15)4/h6-10,16H,5,11-12H2,1-4H3,(H,20,23)

Standard InChI Key:  ZPVVOKSYONOZRG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.8968    8.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    8.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0030    8.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465    7.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2445    7.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396    5.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380    5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    5.9922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2768    5.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    3.5979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013    5.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    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
  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  2  0
 17 18  1  0
 18 21  2  0
 20 19  2  0
 19 16  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3407673

   2-(4-Ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)-N-(1-methyl-1H-indol-5-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: 343.43

Molecular Weight (Monoisotopic): 343.1896

AlogP: 2.53

#Rotatable Bonds: 4

Polar Surface Area: 63.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.86

CX Basic pKa: 6.10

CX LogP: 2.38

CX LogD: 2.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.72

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