1-Methyl-3-(2,4,6-trimethoxybenzyliden)indolin-2-one

ID: ALA1086939

PubChem CID: 46889130

Max Phase: Preclinical

Molecular Formula: C18H16ClNO4

Molecular Weight: 345.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(/C=C2/C(=O)Nc3ccc(Cl)cc32)c(OC)c1

Standard InChI:  InChI=1S/C18H16ClNO4/c1-22-11-7-16(23-2)14(17(8-11)24-3)9-13-12-6-10(19)4-5-15(12)20-18(13)21/h4-9H,1-3H3,(H,20,21)/b13-9+

Standard InChI Key:  XCYXSXCVCRBPBV-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.3897  -16.4835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8820  -15.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3971  -15.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5257  -12.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1197  -13.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5454  -13.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3731  -13.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7731  -12.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3490  -12.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7958  -14.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7076  -15.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6058  -16.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6159  -15.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9092  -14.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1919  -15.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1857  -16.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8930  -16.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4802  -14.9663    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.0998  -11.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5036  -10.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5985  -12.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0268  -13.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1414  -14.4525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3159  -14.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  2  0
  1  2  1  0
  5  6  1  0
 12 13  2  0
  2  3  1  0
 13 14  1  0
  6  7  2  0
 14 15  2  0
  3 13  1  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
 12  1  1  0
 15 18  1  0
  8  9  2  0
  4 19  1  0
  9  4  1  0
 19 20  1  0
  8 21  1  0
  7 10  1  0
 21 22  1  0
 10  3  2  0
  6 23  1  0
  4  5  2  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086939

   (3E)-5-chloro-3-[(2,4,6-trimethoxyphenyl)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: 345.78

Molecular Weight (Monoisotopic): 345.0768

AlogP: 3.86

#Rotatable Bonds: 4

Polar Surface Area: 56.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.28

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: -0.38

References

1. Höttecke N, Liebeck M, Baumann K, Schubenel R, Winkler E, Steiner H, Schmidt B..  (2010)  Inhibition of gamma-secretase by the CK1 inhibitor IC261 does not depend on CK1delta.,  20  (9): [PMID:20350806] [10.1016/j.bmcl.2010.02.110]

Source

Source(1):

• Scientific Literature