(3S,7aR,11aR)-3-isopropyl-9-((6-(trifluoromethyl)pyridin-3-yl)methyl)octahydrooxazolo[2,3-j][1,6]naphthyridin-5(6H)-one

ID: ALA5202255

PubChem CID: 168292664

Max Phase: Preclinical

Molecular Formula: C20H26F3N3O2

Molecular Weight: 397.44

Names and Identifiers

Canonical SMILES:  CC(C)[C@H]1CO[C@]23CCN(Cc4ccc(C(F)(F)F)nc4)C[C@H]2CCC(=O)N13

Standard InChI:  InChI=1S/C20H26F3N3O2/c1-13(2)16-12-28-19-7-8-25(11-15(19)4-6-18(27)26(16)19)10-14-3-5-17(24-9-14)20(21,22)23/h3,5,9,13,15-16H,4,6-8,10-12H2,1-2H3/t15-,16-,19-/m1/s1

Standard InChI Key:  SSCSXGXGTCGKOK-GPMSIDNRSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.6015    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727   -0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871   -0.4600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015   -0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871   -1.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729   -1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -1.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -1.6967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -2.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -2.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729   -2.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674   -2.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817   -2.5217    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543   -3.6497    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -3.6497    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    2.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    2.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    2.0150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716    2.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6717    0.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    3.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817    3.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3019    3.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    3.2522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.3651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  3 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  2 21  1  6
 21 22  1  0
 23 22  1  0
 24 23  1  0
  2 24  1  0
 22 25  1  6
 25 26  1  0
 25 27  1  0
 20 28  2  0
  3 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5202255

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 397.44

Molecular Weight (Monoisotopic): 397.1977

AlogP: 3.30

#Rotatable Bonds: 3

Polar Surface Area: 45.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.80

CX LogP: 3.39

CX LogD: 2.85

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -0.54

References

1. Dam S, Tangara S, Hamela C, Hattabi T, Faïon L, Carre P, Antoine R, Herledan A, Leroux F, Piveteau C, Eveque M, Flipo M, Deprez B, Kremer L, Willand N, Villemagne B, Hartkoorn RC..  (2022)  Tricyclic SpiroLactams Kill Mycobacteria In Vitro and In Vivo by Inhibiting Type II NADH Dehydrogenases.,  65  (24.0): [PMID:36473699] [10.1021/acs.jmedchem.2c01493]

Source

Source(1):

• Scientific Literature