(3S,7aR,11aR)-9-benzyl-3-isopropyloctahydrooxazolo[2,3-j][1,6]naphthyridin-5(6H)-one

ID: ALA5182198

PubChem CID: 168275580

Max Phase: Preclinical

Molecular Formula: C20H28N2O2

Molecular Weight: 328.46

Names and Identifiers

Canonical SMILES:  CC(C)[C@H]1CO[C@]23CCN(Cc4ccccc4)C[C@H]2CCC(=O)N13

Standard InChI:  InChI=1S/C20H28N2O2/c1-15(2)18-14-24-20-10-11-21(12-16-6-4-3-5-7-16)13-17(20)8-9-19(23)22(18)20/h3-7,15,17-18H,8-14H2,1-2H3/t17-,18-,20-/m1/s1

Standard InChI Key:  XJYVCBMQCHHPSW-QWFCFKBJSA-N

Molfile:  

 
     RDKit          2D

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   -0.1728    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1728   -0.8182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1728    1.6569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    1.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9575    0.5769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423    1.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    2.8941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    2.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1728   -1.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413   -2.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2558   -1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -2.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576   -3.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413   -2.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.0069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    2.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    3.2918    0.0000 C   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
  1  6  1  0
  6  5  1  0
  2  7  1  6
  8  7  1  0
  9  8  1  0
 10  9  1  0
  3 10  1  0
  7 11  1  0
  2 12  1  0
 12 13  1  0
 13 11  1  0
  8 14  2  0
 11 15  1  6
  5 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
  3 23  1  1
 15 24  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5182198

   ---

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: 328.46

Molecular Weight (Monoisotopic): 328.2151

AlogP: 2.88

#Rotatable Bonds: 3

Polar Surface Area: 32.78

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.83

CX LogP: 3.34

CX LogD: 1.90

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -0.10

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