5-chloro-3-(4-(3-chloropropoxy)benzylidene)indolin-2-one

ID: ALA2206028

PubChem CID: 71457713

Max Phase: Preclinical

Molecular Formula: C18H15Cl2NO2

Molecular Weight: 348.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccc(Cl)cc2/C1=C/c1ccc(OCCCCl)cc1

Standard InChI:  InChI=1S/C18H15Cl2NO2/c19-8-1-9-23-14-5-2-12(3-6-14)10-16-15-11-13(20)4-7-17(15)21-18(16)22/h2-7,10-11H,1,8-9H2,(H,21,22)/b16-10-

Standard InChI Key:  PFBSBFFUFZPNAB-YBEGLDIGSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   22.2155   -3.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2143   -4.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9224   -5.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9206   -3.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6292   -3.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6295   -4.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4081   -4.9969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8891   -4.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4077   -3.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7063   -4.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6599   -2.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4592   -2.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0025   -3.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8011   -3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0540   -2.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5022   -1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7057   -1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5076   -3.5207    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.8531   -2.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4009   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1999   -2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7478   -3.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5468   -3.0870    0.0000 Cl  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
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206028

   (3Z)-5-chloro-3-[[4-(3-chloropropoxy)phenyl]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: 348.23

Molecular Weight (Monoisotopic): 347.0480

AlogP: 4.84

#Rotatable Bonds: 5

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: 4.44

CX LogD: 4.44

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: -0.72

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