(R)-2,6-difluoro-3-((2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)pentyl)oxy)benzamide

ID: ALA5081559

PubChem CID: 166627334

Max Phase: Preclinical

Molecular Formula: C18H17F2N5O5

Molecular Weight: 421.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC[C@H](COc1ccc(F)c(C(N)=O)c1F)Nc1ccc([N+](=O)[O-])c2nonc12

Standard InChI:  InChI=1S/C18H17F2N5O5/c1-2-3-9(8-29-13-7-4-10(19)14(15(13)20)18(21)26)22-11-5-6-12(25(27)28)17-16(11)23-30-24-17/h4-7,9,22H,2-3,8H2,1H3,(H2,21,26)/t9-/m1/s1

Standard InChI Key:  BUJJQAFTRAMDEK-SECBINFHSA-N

Molfile:  

 
     RDKit          2D

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    4.3735  -13.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722  -14.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0871  -14.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8034  -14.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8006  -13.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853  -13.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0823  -12.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7956  -12.0601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667  -12.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5135  -13.2973    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589  -13.3039    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5186  -14.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2323  -14.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9475  -14.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6613  -14.5385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3763  -14.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3732  -15.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0875  -16.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8023  -15.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0835  -14.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7971  -14.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4013  -14.3858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0610  -13.6400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2467  -13.7331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5202  -16.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2331  -15.7672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5231  -17.0072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9488  -15.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2349  -16.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2363  -17.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  7  9  2  0
  6  7  1  0
  5 10  1  0
  1 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 21  1  0
 20 16  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 20  2  0
 25 26  2  0
 25 27  1  0
 19 25  1  0
 14 28  1  6
 28 29  1  0
 29 30  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5081559

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.36

Molecular Weight (Monoisotopic): 421.1198

AlogP: 3.17

#Rotatable Bonds: 9

Polar Surface Area: 146.41

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -1.35

References

1. Huecas S, Araújo-Bazán L, Ruiz FM, Ruiz-Ávila LB, Martínez RF, Escobar-Peña A, Artola M, Vázquez-Villa H, Martín-Fontecha M, Fernández-Tornero C, López-Rodríguez ML, Andreu JM..  (2021)  Targeting the FtsZ Allosteric Binding Site with a Novel Fluorescence Polarization Screen, Cytological and Structural Approaches for Antibacterial Discovery.,  64  (9.0): [PMID:33908781] [10.1021/acs.jmedchem.0c02207]

Source

Source(1):

• Scientific Literature