2-(2-chloro-3,4-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one

ID: ALA5283933

Max Phase: Preclinical

Molecular Formula: C19H17ClO3

Molecular Weight: 328.80

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\CCc3ccccc3C2=O)c(Cl)c1OC

Standard InChI:  InChI=1S/C19H17ClO3/c1-22-16-10-9-13(17(20)19(16)23-2)11-14-8-7-12-5-3-4-6-15(12)18(14)21/h3-6,9-11H,7-8H2,1-2H3/b14-11+

Standard InChI Key:  MWZVEXVGCCUGQP-SDNWHVSQSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.0792   -8.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0833   -9.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7996   -9.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7975   -8.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0771   -7.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5138   -8.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2279   -8.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2300   -9.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9442   -9.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6603   -9.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6582   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9441   -8.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9412  -10.5803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6568  -10.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3650   -9.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -8.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6533   -8.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381   -8.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404   -9.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6543   -9.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5140   -9.7552    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.3742   -9.7522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0892   -9.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0
 15  2  1  0
  2  3  1  0
  3  4  1  0
  1  4  1  0
  1  5  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  4  6  2  0
 13 14  1  0
  9 13  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  8 21  1  0
 22 23  1  0
 10 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283933

   ---

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: 328.80

Molecular Weight (Monoisotopic): 328.0866

AlogP: 4.57

#Rotatable Bonds: 3

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -0.24

References

1. Qin HL, Leng J, Zhang CP, Jantan I, Amjad MW, Sher M, Naeem-Ul-Hassan M, Hussain MA, Bukhari SN..  (2016)  Synthesis of α,β-Unsaturated Carbonyl-Based Compounds, Oxime and Oxime Ether Analogs as Potential Anticancer Agents for Overcoming Cancer Multidrug Resistance by Modulation of Efflux Pumps in Tumor Cells.,  59  (7): [PMID:27010345] [10.1021/acs.jmedchem.6b00276]

Source

Source(1):

• Scientific Literature