3-(4-butoxybenzyliden)-5-chloroindolin-2-one

ID: ALA2206031

PubChem CID: 2470340

Max Phase: Preclinical

Molecular Formula: C19H18ClNO2

Molecular Weight: 327.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(/C=C2\C(=O)Nc3ccc(Cl)cc32)cc1

Standard InChI:  InChI=1S/C19H18ClNO2/c1-2-3-10-23-15-7-4-13(5-8-15)11-17-16-12-14(20)6-9-18(16)21-19(17)22/h4-9,11-12H,2-3,10H2,1H3,(H,21,22)/b17-11-

Standard InChI Key:  HPTWABVHEZXCFE-BOPFTXTBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   22.4878  -11.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4867  -12.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1948  -12.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1930  -11.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9016  -11.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9018  -12.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6805  -12.4837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1615  -11.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6801  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9787  -11.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9323  -10.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7316  -10.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2749  -10.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0735  -10.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3264   -9.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7746   -9.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9781   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7800  -11.0074    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.1255   -9.7035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6733  -10.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4723  -10.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0202  -10.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8192  -10.5738    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
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206031

   (3Z)-3-[(4-butoxyphenyl)methylidene]-5-chloro-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: 327.81

Molecular Weight (Monoisotopic): 327.1026

AlogP: 5.01

#Rotatable Bonds: 5

Polar Surface Area: 38.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.29

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -0.72

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