2-(2-Bromo-3,4,5-trimethoxy-benzylidene)-7,8-dimethoxy-tetralone

ID: ALA5282265

Max Phase: Preclinical

Molecular Formula: C22H23BrO6

Molecular Weight: 463.32

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(=O)/C(=C/c1cc(OC)c(OC)c(OC)c1Br)CC2

Standard InChI:  InChI=1S/C22H23BrO6/c1-25-16-9-12-6-7-13(20(24)15(12)11-17(16)26-2)8-14-10-18(27-3)21(28-4)22(29-5)19(14)23/h8-11H,6-7H2,1-5H3/b13-8+

Standard InChI Key:  GNAYGWINHYUXMR-MDWZMJQESA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   12.6987   -8.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7029   -9.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4191   -9.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4170   -8.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6967   -7.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1332   -8.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8473   -8.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8494   -9.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5635   -9.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2796   -9.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2776   -8.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5635   -8.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5607  -10.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761  -11.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9847   -9.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9862   -8.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2729   -8.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5577   -8.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5601   -9.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2740   -9.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8430   -8.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1277   -8.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8458   -9.7746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8485  -10.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9889   -8.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9875   -7.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9935   -9.7603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7084   -9.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1334   -9.7635    0.0000 Br  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
 21 22  1  0
 18 21  1  0
 23 24  1  0
 19 23  1  0
 25 26  1  0
 11 25  1  0
 27 28  1  0
 10 27  1  0
  8 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282265

   ---

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: 463.32

Molecular Weight (Monoisotopic): 462.0678

AlogP: 4.70

#Rotatable Bonds: 6

Polar Surface Area: 63.22

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.32

CX LogD: 4.32

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 0.23

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