N-(2-((S)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-1,3-trans-dioxan-5-yl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxamide

ID: ALA5177294

PubChem CID: 168277386

Max Phase: Preclinical

Molecular Formula: C23H22FN5O7

Molecular Weight: 499.46

Names and Identifiers

Canonical SMILES:  COc1ccc2ncc(F)c(C[C@H](O)[C@H]3OC[C@H](NC(=O)c4ccc5c(n4)NC(=O)CO5)CO3)c2n1

Standard InChI:  InChI=1S/C23H22FN5O7/c1-33-19-5-3-14-20(29-19)12(13(24)7-25-14)6-16(30)23-35-8-11(9-36-23)26-22(32)15-2-4-17-21(27-15)28-18(31)10-34-17/h2-5,7,11,16,23,30H,6,8-10H2,1H3,(H,26,32)(H,27,28,31)/t11-,16-,23-/m0/s1

Standard InChI Key:  GOMYQMSOGFDKOC-QNEUBCLTSA-N

Molfile:  

 
     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   -4.3365   -1.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3405   -2.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174   -2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174   -1.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -1.2774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2120   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   -1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984   -2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -2.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -1.2650    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.8964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -0.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4239   -0.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8363    0.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    0.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887    0.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.0880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    0.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117    0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5242    0.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117    1.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950    1.5028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5242    2.2124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3493    2.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7577    1.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410    0.7850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -0.6957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0501   -1.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7596   -1.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6593    1.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7596    2.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  5  6  2  0
  6  1  1  0
  7  5  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  8 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 18 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 27 26  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 30 29  1  0
 31 30  1  0
 32 31  1  0
 26 32  1  0
 15 33  1  6
  1 34  1  0
 34 35  1  0
 22 36  2  0
 30 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5177294

   ---

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: 499.46

Molecular Weight (Monoisotopic): 499.1503

AlogP: 0.58

#Rotatable Bonds: 6

Polar Surface Area: 154.02

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.01

CX Basic pKa: 2.00

CX LogP: 1.00

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.44

Np Likeness Score: -0.66

References

1. Lu Y, Mann CA, Nolan S, Collins JA, Parker E, Papa J, Vibhute S, Jahanbakhsh S, Thwaites M, Hufnagel D, Hazbón MH, Moreno J, Stedman TT, Wittum T, Wozniak DJ, Osheroff N, Yalowich JC, Mitton-Fry MJ..  (2022)  1,3-Dioxane-Linked Novel Bacterial Topoisomerase Inhibitors: Expanding Structural Diversity and the Antibacterial Spectrum.,  13  (6.0): [PMID:35707162] [10.1021/acsmedchemlett.2c00111]

Source

Source(1):

• Scientific Literature