(Z)-3-(2-(2-(1-allyl-2-oxoindolin-3-ylidene)hydrazinyl)-2-oxoacetamido)benzoic acid

ID: ALA2323031

Cas Number: 883791-50-2

PubChem CID: 3595217

Max Phase: Preclinical

Molecular Formula: C20H16N4O5

Molecular Weight: 392.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)/C(=N\NC(=O)C(=O)Nc2cccc(C(=O)O)c2)c2ccccc21

Standard InChI:  InChI=1S/C20H16N4O5/c1-2-10-24-15-9-4-3-8-14(15)16(19(24)27)22-23-18(26)17(25)21-13-7-5-6-12(11-13)20(28)29/h2-9,11H,1,10H2,(H,21,25)(H,23,26)(H,28,29)/b22-16-

Standard InChI Key:  VPOGUPFTDTXHJI-JWGURIENSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   33.8501   -2.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8490   -3.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5570   -3.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5552   -2.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2638   -2.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2687   -3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0530   -3.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5331   -2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0452   -2.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2932   -1.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7428   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9908    0.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3502   -2.8101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3101   -4.2595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1104   -4.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3675   -5.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1678   -5.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8242   -5.8109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4248   -6.1414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7110   -4.7552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8816   -6.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0849   -6.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5419   -7.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7988   -7.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6038   -8.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1433   -7.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7388   -7.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4821   -6.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1952   -7.6376    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  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
  7 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 17 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  1  0
 27 29  2  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2323031

   3-(2-(2-(1-Allyl-2-oxoindolin-3-ylidene)hydrazineyl)-2-oxoacetamido)benzoic 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: 392.37

Molecular Weight (Monoisotopic): 392.1121

AlogP: 1.38

#Rotatable Bonds: 5

Polar Surface Area: 128.17

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.92

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: -1.18

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.47

References

1. Zhang M, Catrow JL, Ji H..  (2013)  High-Throughput Selectivity Assays for Small-Molecule Inhibitors of β-Catenin/T-Cell Factor Protein-Protein Interactions.,  4  (2): [PMID:24900664] [10.1021/ml300367f]

Source

Source(1):

• Scientific Literature