(E)-N-hydroxy-3-(4-(((3-(naphthalen-1-yl)ureido)oxy)methyl)phenyl)acrylamide

ID: ALA4568030

PubChem CID: 155560660

Max Phase: Preclinical

Molecular Formula: C21H19N3O4

Molecular Weight: 377.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(CONC(=O)Nc2cccc3ccccc23)cc1)NO

Standard InChI:  InChI=1S/C21H19N3O4/c25-20(23-27)13-12-15-8-10-16(11-9-15)14-28-24-21(26)22-19-7-3-5-17-4-1-2-6-18(17)19/h1-13,27H,14H2,(H,23,25)(H2,22,24,26)/b13-12+

Standard InChI Key:  KBZKKCRWOQRYGE-OUKQBFOZSA-N

Molfile:  

 
     RDKit          2D

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   22.1070   -8.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8150   -9.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5247   -8.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5219   -7.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8133   -7.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3990   -9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6916   -8.7468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2280   -7.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9373   -7.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6434   -7.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3527   -7.9141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6404   -6.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0589   -7.5028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9836   -9.1548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2762   -8.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5681   -9.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2768   -7.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8608   -8.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4508   -7.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4528   -8.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1599   -9.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1598   -7.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8629   -7.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5670   -7.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5693   -6.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8615   -6.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1603   -6.7110    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
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 11 13  2  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
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 16 18  2  0
 17 19  1  0
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 23 20  2  0
 20 21  1  0
 21 22  2  0
 22 19  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4568030

   ---

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: 377.40

Molecular Weight (Monoisotopic): 377.1376

AlogP: 3.61

#Rotatable Bonds: 6

Polar Surface Area: 99.69

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.74

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