2-carboxymethyl-4-methoxy-7-phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-one

ID: ALA204766

PubChem CID: 11551991

Max Phase: Preclinical

Molecular Formula: C20H16N2O4

Molecular Weight: 348.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2c([nH]1)c(OC)cc1nc(-c3ccccc3)cc(O)c12

Standard InChI:  InChI=1S/C20H16N2O4/c1-25-17-10-14-18(12-8-15(20(24)26-2)22-19(12)17)16(23)9-13(21-14)11-6-4-3-5-7-11/h3-10,22H,1-2H3,(H,21,23)

Standard InChI Key:  COZYLVXQETWOEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.4726  -13.8869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0601  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4726  -15.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976  -15.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5351  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9476  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5351  -13.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101  -13.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7577  -14.0592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881  -15.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8426  -14.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101  -16.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226  -15.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976  -15.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9476  -12.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7726  -12.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5584  -15.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2701  -14.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5594  -16.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0464  -15.4012    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  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
  2 15  1  0
 21 22  1  0
  8 21  1  0
 24 26  1  0
 23 24  1  0
 13 23  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA204766

   Methyl 4-methoxy-9-oxo-7-phenyl-3,6-dihydropyrrolo[3,2-f]quinoline-2-carboxylate

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: 348.36

Molecular Weight (Monoisotopic): 348.1110

AlogP: 3.88

#Rotatable Bonds: 3

Polar Surface Area: 84.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.83

CX Basic pKa: 0.92

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.17

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