3-[4-(2,3-dihydro-1H-indol-1-yl)-3-nitrophenyl]-1,2,3-oxadiazol-3-ium-5-olate

ID: ALA98684

PubChem CID: 405163

Max Phase: Preclinical

Molecular Formula: C16H12N4O4

Molecular Weight: 324.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-[n+]2cc([O-])on2)ccc1N1CCc2ccccc21

Standard InChI:  InChI=1S/C16H12N4O4/c21-16-10-19(17-24-16)12-5-6-14(15(9-12)20(22)23)18-8-7-11-3-1-2-4-13(11)18/h1-6,9-10H,7-8H2

Standard InChI Key:  REIKGZJBRJPXAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.3917    1.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417    0.6958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -1.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917    1.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -1.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -1.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917    2.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  2  0
  3  7  1  0
  4  1  2  0
  5  2  1  0
  6  1  1  0
  7 14  2  0
  8  6  2  0
  9 11  1  0
 10  4  1  0
 11  1  1  0
 12  3  1  0
 13  3  1  0
 14 19  1  0
 15  5  1  0
 16  5  2  0
 17  8  1  0
 18 12  2  0
 19 11  2  0
 20 13  1  0
 21 12  1  0
 22 18  1  0
 23 21  2  0
 24 23  1  0
 10  8  1  0
  7  2  1  0
 20 18  1  0
 22 24  2  0
M  CHG  4   1   1   5   1  15  -1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA98684

   N-(4-Indoline-1-yl-3-nitrophenyl)sydnone

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: 324.30

Molecular Weight (Monoisotopic): 324.0859

AlogP: 1.63

#Rotatable Bonds: 3

Polar Surface Area: 99.35

Molecular Species: ACID

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.98

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.41

Np Likeness Score: -1.02

References

1. Dunkley CS, Thoman CJ..  (2003)  Synthesis and biological evaluation of a novel phenyl substituted sydnone series as potential antitumor agents.,  13  (17): [PMID:14611853] [10.1016/s0960-894x(03)00487-6]

Source

Source(1):

• Scientific Literature