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

ID: ALA429086

PubChem CID: 23634556

Max Phase: Preclinical

Molecular Formula: C22H22N2O

Molecular Weight: 330.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCn1ccc2c3c(=O)cc(-c4ccccc4)[nH]c3ccc21

Standard InChI:  InChI=1S/C22H22N2O/c1-2-3-7-13-24-14-12-17-20(24)11-10-18-22(17)21(25)15-19(23-18)16-8-5-4-6-9-16/h4-6,8-12,14-15H,2-3,7,13H2,1H3,(H,23,25)

Standard InChI Key:  ZWEXCFHQOXSQKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.4605   -6.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -7.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -7.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902   -7.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -6.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -6.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021   -6.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -6.4580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3173   -4.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985   -5.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -3.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -5.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312   -6.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -6.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4587   -6.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464   -4.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4567   -5.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0655   -4.6757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188   -4.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8926   -4.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3150   -3.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1415   -3.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5597   -3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3862   -3.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
 15 17  1  0
 16 12  1  0
 16 17  2  0
  7  8  1  0
  3  4  2  0
  4  5  1  0
  7 10  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
  8 13  1  0
 18 21  1  0
 12  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  1  0
  2  3  1  0
 23 24  1  0
  9 11  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA429086

   3-pentyl-7-phenyl-6H-pyrrolo[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: 330.43

Molecular Weight (Monoisotopic): 330.1732

AlogP: 5.34

#Rotatable Bonds: 5

Polar Surface Area: 37.79

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.49

CX LogP: 5.34

CX LogD: 5.34

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -0.62

References

1. Gasparotto V, Castagliuolo I, Ferlin MG..  (2007)  3-substituted 7-phenyl-pyrroloquinolinones show potent cytotoxic activity in human cancer cell lines.,  50  (22): [PMID:17915851] [10.1021/jm070534b]

Source

Source(1):

• Scientific Literature