N-(3-(5-ethylbenzo[d]oxazol-2-yl)phenyl)-5-nitrofuran-2-carboxamide

ID: ALA1632112

PubChem CID: 1270329

Max Phase: Preclinical

Molecular Formula: C20H15N3O5

Molecular Weight: 377.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc2oc(-c3cccc(NC(=O)c4ccc([N+](=O)[O-])o4)c3)nc2c1

Standard InChI:  InChI=1S/C20H15N3O5/c1-2-12-6-7-16-15(10-12)22-20(28-16)13-4-3-5-14(11-13)21-19(24)17-8-9-18(27-17)23(25)26/h3-11H,2H2,1H3,(H,21,24)

Standard InChI Key:  UIQRZGLZDWPCJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.3718  -14.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549  -14.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1520  -13.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3635  -13.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213  -13.0351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313  -12.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765  -13.3673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396  -13.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566  -13.2368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3475  -14.6657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725  -14.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855  -13.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4097  -13.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200  -14.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742  -15.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983  -15.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8004  -16.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6199  -16.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4563  -16.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630  -17.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7792  -17.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4877  -17.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4811  -18.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601  -18.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547  -18.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502  -19.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4597  -19.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  2  0
 16 12  1  0
 17 15  1  0
  6  7  2  0
 16 17  2  0
  6  8  1  0
  3  6  1  0
 18 19  1  0
  3  4  1  0
  5  9  1  0
  4  5  1  0
 19 22  1  0
 21 20  1  0
 20 18  2  0
 17 18  1  0
  9 10  2  0
  5  1  2  0
 21 22  2  0
  9 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 12 13  2  0
 25 27  1  0
  2  3  2  0
 27 28  1  0
M  CHG  2   6   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1632112

   N-[3-(5-ethyl-1,3-benzoxazol-2-yl)phenyl]-5-nitrofuran-2-carboxamide

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: 377.36

Molecular Weight (Monoisotopic): 377.1012

AlogP: 4.81

#Rotatable Bonds: 5

Polar Surface Area: 111.41

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.23

CX Basic pKa: 0.51

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -2.05

References

1. Cheng TJ, Wu YT, Yang ST, Lo KH, Chen SK, Chen YH, Huang WI, Yuan CH, Guo CW, Huang LY, Chen KT, Shih HW, Cheng YS, Cheng WC, Wong CH..  (2010)  High-throughput identification of antibacterials against methicillin-resistant Staphylococcus aureus (MRSA) and the transglycosylase.,  18  (24): [PMID:21075637] [10.1016/j.bmc.2010.10.036]

Source

Source(1):

• Scientific Literature