5-chloro-3-(4-methoxybenzyliden)indolin-2-one

ID: ALA2206030

PubChem CID: 2338583

Max Phase: Preclinical

Molecular Formula: C16H12ClNO2

Molecular Weight: 285.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\C(=O)Nc3ccc(Cl)cc32)cc1

Standard InChI:  InChI=1S/C16H12ClNO2/c1-20-12-5-2-10(3-6-12)8-14-13-9-11(17)4-7-15(13)18-16(14)19/h2-9H,1H3,(H,18,19)/b14-8-

Standard InChI Key:  VFGCMJDXLFMWON-ZSOIEALJSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   12.3431  -11.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3420  -12.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0500  -12.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0482  -11.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7569  -11.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7571  -12.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5358  -12.6116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0168  -11.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5353  -11.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8340  -11.9488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7876  -10.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5869  -10.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1301  -10.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9287  -10.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1817  -10.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6299   -9.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8333   -9.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6353  -11.1354    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9807   -9.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2320   -9.0538    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  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
 15 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206030

   (3Z)-5-chloro-3-[(4-methoxyphenyl)methylidene]-1H-indol-2-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: 285.73

Molecular Weight (Monoisotopic): 285.0557

AlogP: 3.84

#Rotatable Bonds: 2

Polar Surface Area: 38.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.29

CX Basic pKa: ┄

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.85

Np Likeness Score: -0.63

References

1. Amombo GM, Kramer T, Lo Monte F, Göring S, Fach M, Smith S, Kolb S, Schubenel R, Baumann K, Schmidt B..  (2012)  Modification of a promiscuous inhibitor shifts the inhibition from γ-secretase to FLT-3.,  22  (24): [PMID:23107479] [10.1016/j.bmcl.2012.10.016]

Source

Source(1):

• Scientific Literature