2-(2-Bromo-3,4,5-trimethoxy-benzylidene)-5-hydroxy-tetralone

ID: ALA5286155

Max Phase: Preclinical

Molecular Formula: C20H19BrO5

Molecular Weight: 419.27

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CCc3c(O)cccc3C2=O)c(Br)c(OC)c1OC

Standard InChI:  InChI=1S/C20H19BrO5/c1-24-16-10-12(17(21)20(26-3)19(16)25-2)9-11-7-8-13-14(18(11)23)5-4-6-15(13)22/h4-6,9-10,22H,7-8H2,1-3H3/b11-9+

Standard InChI Key:  IFGMAUVCWFFMTB-PKNBQFBNSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.2927  -17.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2969  -19.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0130  -19.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0109  -18.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2906  -17.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7272  -17.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4413  -18.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4434  -19.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1575  -19.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8736  -19.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8716  -18.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1575  -17.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1545  -20.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8701  -20.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5786  -19.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5802  -18.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8669  -17.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517  -18.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541  -19.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8679  -19.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5874  -19.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3024  -19.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7274  -19.5120    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5828  -17.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5813  -17.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8699  -20.3445    0.0000 O   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
 10 21  1  0
  8 23  1  0
 24 25  1  0
 11 24  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286155

   ---

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: 419.27

Molecular Weight (Monoisotopic): 418.0416

AlogP: 4.39

#Rotatable Bonds: 4

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.32

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: 0.36

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