6-[4-(Acetamido)benzylidene]-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one

ID: ALA5286444

Max Phase: Preclinical

Molecular Formula: C19H15NO4

Molecular Weight: 321.33

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(/C=C2\Cc3cc4c(cc3C2=O)OCO4)cc1

Standard InChI:  InChI=1S/C19H15NO4/c1-11(21)20-15-4-2-12(3-5-15)6-14-7-13-8-17-18(24-10-23-17)9-16(13)19(14)22/h2-6,8-9H,7,10H2,1H3,(H,20,21)/b14-6+

Standard InChI Key:  JFACWUIDVSYPAX-MKMNVTDBSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -2.5663    1.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    1.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399    1.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399    0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    0.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552    0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551    1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297    1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3542    1.7218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3543    0.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414    2.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549    1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928    0.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -1.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697   -1.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532   -0.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -1.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4285   -1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -2.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -1.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  1  0
  9  7  1  0
  1 10  1  0
  6 11  1  0
 11 12  1  0
 12 10  1  0
  8 13  2  0
  9 14  2  0
 14 15  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286444

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.33

Molecular Weight (Monoisotopic): 321.1001

AlogP: 3.20

#Rotatable Bonds: 2

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -0.25

References

1. Altıntop MD, Özdemir A, Temel HE, Demir Cevizlidere B, Sever B, Kaplancıklı ZA, Akalın Çiftçi G..  (2022)  Design, synthesis and biological evaluation of a new series of arylidene indanones as small molecules for targeted therapy of non-small cell lung carcinoma and prostate cancer.,  244  [PMID:36270087] [10.1016/j.ejmech.2022.114851]

Source

Source(1):

• Scientific Literature