5-chloro-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)indoline

ID: ALA2206025

PubChem CID: 71461363

Max Phase: Preclinical

Molecular Formula: C20H16ClN3O2

Molecular Weight: 365.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\C(=O)Nc3ccc(Cl)cc32)ccc1-n1cnc(C)c1

Standard InChI:  InChI=1S/C20H16ClN3O2/c1-12-10-24(11-22-12)18-6-3-13(8-19(18)26-2)7-16-15-9-14(21)4-5-17(15)23-20(16)25/h3-11H,1-2H3,(H,23,25)/b16-7-

Standard InChI Key:  LUWKNOZCOHZTLD-APSNUPSMSA-N

Molfile:  

     RDKit          2D

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   11.4226   -8.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4215   -9.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1362   -9.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1345   -8.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8498   -8.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8500   -9.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6361   -9.7314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1217   -9.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6357   -8.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9466   -9.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8903   -7.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6972   -7.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2455   -8.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0518   -7.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3071   -7.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7501   -6.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9460   -6.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7081   -8.2412    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6037   -8.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3486   -9.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1138   -6.9248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7258   -7.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4396   -7.0599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2667   -6.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4462   -6.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8176   -5.6392    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
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 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
 14 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206025

   (3Z)-5-chloro-3-[[3-methoxy-4-(4-methylimidazol-1-yl)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: 365.82

Molecular Weight (Monoisotopic): 365.0931

AlogP: 4.34

#Rotatable Bonds: 3

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.29

CX Basic pKa: 5.87

CX LogP: 3.61

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.90

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