(E)-N-hydroxy-3-(4-(((3-(4-methoxyphenyl)ureido)oxy)methyl)phenyl)acrylamide

ID: ALA4535463

PubChem CID: 155547606

Max Phase: Preclinical

Molecular Formula: C18H19N3O5

Molecular Weight: 357.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)NOCc2ccc(/C=C/C(=O)NO)cc2)cc1

Standard InChI:  InChI=1S/C18H19N3O5/c1-25-16-9-7-15(8-10-16)19-18(23)21-26-12-14-4-2-13(3-5-14)6-11-17(22)20-24/h2-11,24H,12H2,1H3,(H,20,22)(H2,19,21,23)/b11-6+

Standard InChI Key:  LZFRGGLRIPWNJS-IZZDOVSWSA-N

Molfile:  

 
     RDKit          2D

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   22.3929   -2.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3918   -3.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0998   -4.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8095   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8067   -2.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0980   -2.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6837   -4.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9764   -3.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5128   -2.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2221   -2.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9282   -2.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6375   -2.9367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9251   -1.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3436   -2.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2683   -4.1774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5609   -3.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8529   -4.1763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5616   -2.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1455   -3.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1512   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4446   -2.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7356   -2.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7376   -3.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4447   -4.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0277   -2.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3202   -2.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535463

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 357.37

Molecular Weight (Monoisotopic): 357.1325

AlogP: 2.47

#Rotatable Bonds: 7

Polar Surface Area: 108.92

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.73

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 2.15

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: -0.69

References

1. Pflieger M, Hamacher A, Öz T, Horstick-Muche N, Boesen B, Schrenk C, Kassack MU, Kurz T..  (2019)  Novel α,β-unsaturated hydroxamic acid derivatives overcome cisplatin resistance.,  27  (19): [PMID:31431326] [10.1016/j.bmc.2019.07.052]

Source

Source(1):

• Scientific Literature