5-chloro-3-(4-hydroxybenzylidene)indolin-2-one

ID: ALA2206029

PubChem CID: 71461364

Max Phase: Preclinical

Molecular Formula: C15H10ClNO2

Molecular Weight: 271.70

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H10ClNO2/c16-10-3-6-14-12(8-10)13(15(19)17-14)7-9-1-4-11(18)5-2-9/h1-8,18H,(H,17,19)/b13-7-

Standard InChI Key:  UKVCHQYKDKIMCB-QPEQYQDCSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    2.0663  -11.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652  -12.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732  -13.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7714  -11.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4801  -11.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803  -12.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590  -12.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400  -12.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585  -11.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5572  -12.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108  -10.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101  -10.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533  -11.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6519  -11.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9049  -10.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3531   -9.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565   -9.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585  -11.3872    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7039  -10.0832    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2206029

   (3Z)-5-chloro-3-[(4-hydroxyphenyl)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: 271.70

Molecular Weight (Monoisotopic): 271.0400

AlogP: 3.54

#Rotatable Bonds: 1

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.85

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.78

Np Likeness Score: -0.32

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