2-(2-bromo-3,4,5-trimethoxybenzylidene)-4-methyl-3,4-dihydronaphthalen-1(2H)-one oxime

ID: ALA5285192

Max Phase: Preclinical

Molecular Formula: C21H22BrNO4

Molecular Weight: 432.31

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CC(C)c3ccccc3\C2=N\O)c(Br)c(OC)c1OC

Standard InChI:  InChI=1S/C21H22BrNO4/c1-12-9-14(19(23-24)16-8-6-5-7-15(12)16)10-13-11-17(25-2)20(26-3)21(27-4)18(13)22/h5-8,10-12,24H,9H2,1-4H3/b14-10+,23-19+

Standard InChI Key:  SYFDSUKODVFXKW-CYZHIAODSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    7.4028  -19.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1173  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1173  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4028  -20.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6885  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742  -20.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2598  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742  -19.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6885  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4028  -21.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8317  -19.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5462  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2605  -19.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9748  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9748  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2605  -20.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5462  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2605  -21.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9748  -22.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6893  -20.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4036  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6893  -19.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4036  -19.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4028  -18.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1173  -17.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8317  -20.8570    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  4 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  1  0
 17 19  1  0
 21 22  1  0
 16 21  1  0
 23 24  1  0
 15 23  1  0
  2 12  2  0
 25 26  1  0
  1 25  2  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285192

   ---

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: 432.31

Molecular Weight (Monoisotopic): 431.0732

AlogP: 5.24

#Rotatable Bonds: 4

Polar Surface Area: 60.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.00

CX Basic pKa: 1.94

CX LogP: 4.93

CX LogD: 4.39

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 0.30

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