5-Chloro-3-(2,3,4-trimethoxybenzylidene)indolin-2-one

ID: ALA1086796

PubChem CID: 8856659

Max Phase: Preclinical

Molecular Formula: C18H16ClNO4

Molecular Weight: 345.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2/C(=O)Nc3ccc(Cl)cc32)c(OC)c1OC

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

Standard InChI Key:  KIEKWFPKBYGAJA-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.8895  -16.9016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817  -16.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969  -15.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255  -12.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195  -13.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452  -14.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8729  -14.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2728  -13.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488  -12.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2955  -14.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2073  -16.2466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056  -16.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157  -15.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4090  -15.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918  -15.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856  -16.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3929  -17.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801  -15.3846    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0982  -13.3932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265  -14.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2464  -11.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718  -11.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997  -12.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034  -11.2855    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
  8 19  1  0
  9  4  1  0
 19 20  1  0
  9 21  1  0
  7 10  1  0
 21 22  1  0
 10  3  2  0
  4 23  1  0
  4  5  2  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086796

   (3E)-5-chloro-3-[(2,3,4-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: -0.45

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]

2. 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