methyl 4-(3-acetamido-5-methoxyphenoxy)-7-methoxyquinoline-6-carboxylate

ID: ALA5283099

Max Phase: Preclinical

Molecular Formula: C21H20N2O6

Molecular Weight: 396.40

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2c(Oc3cc(NC(C)=O)cc(OC)c3)ccnc2cc1OC

Standard InChI:  InChI=1S/C21H20N2O6/c1-12(24)23-13-7-14(26-2)9-15(8-13)29-19-5-6-22-18-11-20(27-3)17(10-16(18)19)21(25)28-4/h5-11H,1-4H3,(H,23,24)

Standard InChI Key:  HKWSFYDQCDJRMZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    2.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -2.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    0.2065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    1.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301   -1.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    0.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301   -1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -2.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -3.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  7  8  1  0
  9  3  1  0
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 19 14  1  0
 20  1  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 17 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 18 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283099

   ---

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: 396.40

Molecular Weight (Monoisotopic): 396.1321

AlogP: 3.79

#Rotatable Bonds: 6

Polar Surface Area: 95.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.56

CX Basic pKa: 5.27

CX LogP: 2.56

CX LogD: 2.55

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -0.72

References

1. Lv G, Shi Q, Zhang T, Li J, Long Y, Zhang W, Choudhry N, Yang K, Li H, Kalashova J, Yang C, Zhou X, Reddy MC, Anantoju KK, Zhang S, Zhang J, Allen TD, Liu H, Nimishetti N, Yang D..  (2023)  Integrating a phenotypic screening with a structural simplification strategy to identify 4-phenoxy-quinoline derivatives to potently disrupt the mitotic localization of Aurora kinase B.,  80  [PMID:36696874] [10.1016/j.bmc.2023.117173]

Source

Source(1):

• Scientific Literature