5-chloro-3-(3-methoxy-4-(methylsulfonyl)benzylidene)indolin-2-one

ID: ALA2206024

PubChem CID: 71452402

Max Phase: Preclinical

Molecular Formula: C17H14ClNO4S

Molecular Weight: 363.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\C(=O)Nc3ccc(Cl)cc32)ccc1S(C)(=O)=O

Standard InChI:  InChI=1S/C17H14ClNO4S/c1-23-15-8-10(3-6-16(15)24(2,21)22)7-13-12-9-11(18)4-5-14(12)19-17(13)20/h3-9H,1-2H3,(H,19,20)/b13-7-

Standard InChI Key:  JTPZWWYBRZKSDB-QPEQYQDCSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.4543   -9.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531  -10.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612  -10.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594   -8.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -9.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683  -10.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469  -10.3829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280   -9.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -9.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9451   -9.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -8.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6980   -8.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2413   -8.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0399   -8.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928   -7.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7410   -7.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445   -7.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -8.9067    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0919   -7.6027    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6397   -8.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8748   -6.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4938   -6.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5866   -9.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3340   -9.9365    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
 19 21  2  0
 19 22  2  0
 14 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206024

   (3Z)-5-chloro-3-[(3-methoxy-4-methylsulfonylphenyl)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: 363.82

Molecular Weight (Monoisotopic): 363.0332

AlogP: 3.24

#Rotatable Bonds: 3

Polar Surface Area: 72.47

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: ┄

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: -0.98

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