7-(3'-nitro-phenyl)-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-one

ID: ALA381126

PubChem CID: 11688086

Max Phase: Preclinical

Molecular Formula: C17H11N3O3

Molecular Weight: 305.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(-c2cc(O)c3c(ccc4[nH]ccc43)n2)c1

Standard InChI:  InChI=1S/C17H11N3O3/c21-16-9-15(10-2-1-3-11(8-10)20(22)23)19-14-5-4-13-12(17(14)16)6-7-18-13/h1-9,18H,(H,19,21)

Standard InChI Key:  USVRRCZREISWAA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    6.1861  -15.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5986  -14.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1861  -13.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611  -13.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9486  -14.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1236  -14.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111  -15.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1236  -16.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9486  -16.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611  -15.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9051  -15.1764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747  -14.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203  -14.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9486  -13.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4236  -14.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8361  -13.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6611  -13.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0736  -14.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6611  -15.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8361  -15.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0736  -13.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6611  -12.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8986  -13.2054    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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 12 13  2  0
 11 13  1  0
  6 12  1  0
  7 11  1  0
  4 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 15 20  1  0
 21 22  2  0
 21 23  1  0
 17 21  1  0
  2 15  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA381126

   7-(3-Nitrophenyl)-3,6-dihydropyrrolo[3,2-f]quinolin-9-one

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: 305.29

Molecular Weight (Monoisotopic): 305.0800

AlogP: 4.00

#Rotatable Bonds: 2

Polar Surface Area: 92.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.51

CX Basic pKa: 0.78

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: -0.73

References

1. Gasparotto V, Castagliuolo I, Chiarelotto G, Pezzi V, Montanaro D, Brun P, Palù G, Viola G, Ferlin MG..  (2006)  Synthesis and biological activity of 7-phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-ones: a new class of antimitotic agents devoid of aromatase activity.,  49  (6): [PMID:16539377] [10.1021/jm0510676]

Source

Source(1):

• Scientific Literature