(E)-3-(5-((2-cyanoquinolin-4-yl)(methyl)amino)-2-methoxyphenyl)-N-hydroxyacrylamide

ID: ALA5183440

PubChem CID: 146469200

Max Phase: Preclinical

Molecular Formula: C21H18N4O3

Molecular Weight: 374.40

Names and Identifiers

Canonical SMILES:  COc1ccc(N(C)c2cc(C#N)nc3ccccc23)cc1/C=C/C(=O)NO

Standard InChI:  InChI=1S/C21H18N4O3/c1-25(19-12-15(13-22)23-18-6-4-3-5-17(18)19)16-8-9-20(28-2)14(11-16)7-10-21(26)24-27/h3-12,27H,1-2H3,(H,24,26)/b10-7+

Standard InChI Key:  QHXOKFICRLZQNX-JXMROGBWSA-N

Molfile:  

 
     RDKit          2D

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   -2.8574    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    0.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555   -0.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -0.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838    1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    2.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308    1.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162    0.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014    1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -0.6181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308    1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555   -2.2679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8544    1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692    0.6198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8544    1.8576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    1.0324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  2 10  1  0
  3 11  1  0
 11 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
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 17 16  2  0
 12 17  1  0
 15 18  1  0
 18 19  1  0
 11 20  1  0
  5 21  1  0
 21 22  3  0
 14 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5183440

   ---

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: 374.40

Molecular Weight (Monoisotopic): 374.1379

AlogP: 3.40

#Rotatable Bonds: 5

Polar Surface Area: 98.48

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.55

CX Basic pKa: 3.21

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -0.67

References

1. Hauguel C, Ducellier S, Provot O, Ibrahim N, Lamaa D, Balcerowiak C, Letribot B, Nascimento M, Blanchard V, Askenatzis L, Levaique H, Bignon J, Baschieri F, Bauvais C, Bollot G, Renko D, Deroussent A, Prost B, Laisne MC, Michallet S, Lafanechère L, Papot S, Montagnac G, Tran C, Alami M, Apcher S, Hamze A..  (2022)  Design, synthesis and biological evaluation of quinoline-2-carbonitrile-based hydroxamic acids as dual tubulin polymerization and histone deacetylases inhibitors.,  240  [PMID:35797900] [10.1016/j.ejmech.2022.114573]

Source

Source(1):

• Scientific Literature