6-[(2-bromo-3,4,5-trimethoxyphenyl)methylidene]-5-(hydroxyimino)-5,6,7,8-tetrahydronaphthalen-1-ol

ID: ALA5286853

Max Phase: Preclinical

Molecular Formula: C20H20BrNO5

Molecular Weight: 434.29

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CCc3c(O)cccc3\C2=N\O)c(Br)c(OC)c1OC

Standard InChI:  InChI=1S/C20H20BrNO5/c1-25-16-10-12(17(21)20(27-3)19(16)26-2)9-11-7-8-13-14(18(11)22-24)5-4-6-15(13)23/h4-6,9-10,23-24H,7-8H2,1-3H3/b11-9+,22-18+

Standard InChI Key:  GMICQZYPDHPHBG-KASPCKEOSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.7177  -20.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7177  -22.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890  -22.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890  -20.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1465  -20.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8608  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752  -20.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2895  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2895  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752  -22.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8608  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752  -23.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2895  -23.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0040  -22.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7183  -22.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0040  -20.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7183  -21.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7177  -19.9761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321  -19.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464  -22.4508    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2890  -23.2758    0.0000 O   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
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  1  0
 16 18  1  0
 20 21  1  0
 15 20  1  0
 22 23  1  0
 14 22  1  0
  2 11  2  0
 24 25  1  0
  1 24  2  0
 17 26  1  0
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286853

   ---

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: 434.29

Molecular Weight (Monoisotopic): 433.0525

AlogP: 4.39

#Rotatable Bonds: 4

Polar Surface Area: 80.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.70

CX Basic pKa: 1.31

CX LogP: 4.34

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: 0.31

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