2-(2-chloro-3-methoxybenzylidene)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one

ID: ALA5287426

Max Phase: Preclinical

Molecular Formula: C20H19ClO4

Molecular Weight: 358.82

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(=O)/C(=C/c1cccc(OC)c1Cl)CC2

Standard InChI:  InChI=1S/C20H19ClO4/c1-23-16-6-4-5-13(19(16)21)9-14-8-7-12-10-17(24-2)18(25-3)11-15(12)20(14)22/h4-6,9-11H,7-8H2,1-3H3/b14-9+

Standard InChI Key:  XYMGHHFXYPPIAA-NTEUORMPSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   20.0162   -2.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0204   -4.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7365   -3.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7344   -3.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0141   -1.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4504   -2.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1645   -3.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1666   -3.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8806   -4.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5968   -3.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5946   -3.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8806   -2.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8778   -5.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5931   -5.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3022   -3.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3037   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5906   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8753   -3.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8779   -3.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5916   -4.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1585   -2.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4431   -3.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1635   -4.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1663   -5.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4506   -4.3856    0.0000 Cl  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
  8 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287426

   ---

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: 358.82

Molecular Weight (Monoisotopic): 358.0972

AlogP: 4.58

#Rotatable Bonds: 4

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -0.14

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