(E)-N-{4-[3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)prop-1-enyl]phenyl}aceticacid

ID: ALA2283029

PubChem CID: 76327219

Max Phase: Preclinical

Molecular Formula: C22H18N2O3

Molecular Weight: 358.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccc(/C=C/CN2Cc3cc4ccccc4nc3C2=O)cc1

Standard InChI:  InChI=1S/C22H18N2O3/c25-20(26)12-16-9-7-15(8-10-16)4-3-11-24-14-18-13-17-5-1-2-6-19(17)23-21(18)22(24)27/h1-10,13H,11-12,14H2,(H,25,26)/b4-3+

Standard InChI Key:  SINZJQVVUKDQDA-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -1.0923    0.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0912   -0.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3859    1.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269    0.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276   -0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -0.5910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306    1.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    0.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271   -0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    0.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7825   -1.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260    0.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2373   -0.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544   -0.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4657   -1.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574   -1.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4680   -2.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860   -2.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -1.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2788   -1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6983   -3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5154   -3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9204   -2.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277   -3.9866    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2283029

   2-[4-[(E)-3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2-yl)prop-1-enyl]phenyl]acetic acid

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: 358.40

Molecular Weight (Monoisotopic): 358.1317

AlogP: 3.53

#Rotatable Bonds: 5

Polar Surface Area: 70.50

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.45

CX Basic pKa: 1.23

CX LogP: 3.54

CX LogD: 0.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.11

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