(E)-2-(3-(4-(2-(4-(4-methoxyphenyl)piperazin-1-yl)-2-oxoethyl)phenyl)allyl)-1H-pyrrolo[3,4-b]quinolin-3(2H)-one

ID: ALA2283031

PubChem CID: 76312753

Max Phase: Preclinical

Molecular Formula: C33H32N4O3

Molecular Weight: 532.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2CCN(C(=O)Cc3ccc(/C=C/CN4Cc5cc6ccccc6nc5C4=O)cc3)CC2)cc1

Standard InChI:  InChI=1S/C33H32N4O3/c1-40-29-14-12-28(13-15-29)35-17-19-36(20-18-35)31(38)21-25-10-8-24(9-11-25)5-4-16-37-23-27-22-26-6-2-3-7-30(26)34-32(27)33(37)39/h2-15,22H,16-21,23H2,1H3/b5-4+

Standard InChI Key:  PWZMAJPYZQGMHA-SNAWJCMRSA-N

Molfile:  

     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   -4.1836   -6.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824   -6.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4790   -7.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -5.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -6.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7668   -6.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556   -7.2523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0665   -5.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558   -6.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -6.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667   -7.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826   -6.4264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -5.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -7.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347   -6.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -7.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632   -7.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -7.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -8.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767   -9.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947   -9.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6005   -8.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -7.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -9.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -9.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8291   -9.2326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364  -10.6479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320  -11.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408  -12.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583  -12.0579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0654  -11.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550  -10.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0678  -12.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584  -13.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0673  -14.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853  -14.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928  -13.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8816  -12.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2958  -14.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8891  -15.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 11 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
 30 33  1  0
 36 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283031

   2-[(E)-3-[4-[2-[4-(4-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]phenyl]prop-2-enyl]-1H-pyrrolo[3,4-b]quinolin-3-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: 532.64

Molecular Weight (Monoisotopic): 532.2474

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 65.98

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.73

CX Basic pKa: 3.99

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.34

Np Likeness Score: -0.72

References

1. Nagarapua L, Gaikwad HK, Manikonda SR, Bantu R, Manda KM, Kalivendi SV.  (2013)  Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity,  22  (1): [10.1007/s00044-012-0018-x]

Source

Source(1):

• Scientific Literature